Two Pines Vacation Rentals

There's adventure between every Two Pines

Drew Schug

Your Ultimate Guide to Big Sky Summer Activities

Big Sky, Montana, claims the title as one of the best winter ski havens in the country. But did you know it’s also an incredible summer playground? 

Big Sky holds countless summer activities for every type of traveler. High-country hikes, wild river rides, tranquil trout streams, toe-tapping local events—all await you in this gem of a mountain town. 

From adrenaline-pumping adventures in the mountains to chill evenings under the stars, this guide will help you discover the best Big Sky summer activities and attractions. Whether you’re a couple seeking a romantic wilderness escape or a family gearing up for outdoor fun, Big Sky’s got it all when it comes to summer adventures. So pack your bags and get ready to explore why Big Sky should be at the top of your summer getaway list!

The Best Things to Do in Big Sky in the Summer

1. Hiking Adventures in Big Sky

Ready to immerse yourself in Montana’s famed wilderness? Hiking in Big Sky is the way to go. The Big Sky area offers a vast expanse of towering mountains, cascading waterfalls, and vibrant alpine meadows. Best of all, there are trails for all levels of hikers—everyone can savor the fresh mountain air.

You can take a stroll through lush forests or challenge yourself with a climb to a panoramic peak. Either way, you’re in for breathtaking scenery at every turn. Here are a few of our top trail recommendations in Big Sky: 

  • Beehive Basin Trail: Widely regarded as one of the best summer hikes in Big Sky, this trail leads you through tranquil pine forests to a gorgeous alpine lake surrounded by wildflowers and peaks​. 
  • Ousel Falls: This trail is a local favorite for a short but beautiful hike. It’s a gentle 1.6-mile path that meanders along the Gallatin River, crossing charming wooden bridges before reaching a stunning waterfall oasis in the woods​. 
  • Lava Lake: A highlight of the Gallatin Canyon, the Lava Lake Trail offers a moderate 6-mile round-trip hike that rewards you with a pristine alpine lake nestled beneath rugged cliffs. The trail climbs steadily through shaded forest, following Cascade Creek most of the way, and opens up to sweeping views before reaching the sparkling lake.
  • Storm Castle: If you’re up for a bit more of a challenge, the Storm Castle Trail delivers with steep switchbacks and jaw-dropping summit views. This 5-mile out-and-back trail climbs over 2,000 feet and rewards hikers with panoramic views of the Gallatin River, surrounding canyon walls, and even glimpses of the Spanish Peaks on a clear day. 

Don’t forget—with Yellowstone National Park just a short drive away, you can even tack on a day hike in the park’s incredible backcountry for bonus trails and wildlife sightings​. Whether you stick to the Big Sky area or venture into Yellowstone, you’ll find no shortage of unforgettable hiking adventures.

2. Mountain Biking Thrills

If you prefer two wheels to two feet, Big Sky has you covered. Whether you’re a newbie or a seasoned shredder, the mix of gentle valley trails and challenging alpine terrain makes Big Sky a prime destination for summer mountain biking thrills.

Big Sky Resort turns into a mountain biker’s paradise in summer, with over 50 miles of trails for riders of all levels​. From flowy beginner routes to heart-pounding downhill tracks, you can ride high-speed chairlifts (outfitted with bike racks) up the slopes and then zoom down through forests and wildflower fields. Lift-served downhill mountain biking is a must-try for adrenaline junkies. It’ll get your blood and adrenaline pumping!​

And if you didn’t bring your own bike, no worries. Local shops like Different Spokes at the resort rent out quality mountain bikes and safety gear so you can hit the trails fully equipped​.

Prefer cross-country style biking? Big Sky boasts fantastic singletrack weaving through town and the surrounding National Forest. Many trailheads are accessible right from the highway or local bike shops; for example, the folks at Gallatin Alpine Sports can point you toward a perfect forest trail and set you up with any gear or maps you need​.

3. Fly Fishing on Blue-Ribbon Waters

For those who seek solitude and relaxation (with a side of excitement), fly fishing in Big Sky is not to be missed. The region is home to legendary blue-ribbon trout streams, most notably the Gallatin River, which winds right through Big Sky’s canyon. Visually, the Gallatin River is stunning. In fact, parts of the movie A River Runs Through It were filmed on these waters, and it’s renowned among anglers for its healthy trout populations​. 

You can certainly fish on your own, but hiring a local guide can elevate the experience (especially if you’re new to Montana’s rivers). Outfitters like Gallatin River Guides have been helping anglers find fish in the Gallatin, Madison, and Yellowstone Rivers since 1984​. They’ll take you to the best spots, tie the right flies, and maybe even help you land that bucket-list wild trout. (Insider tip: if you’re staying with Two Pines Vacation Rentals, ask about their partnership perks. Two Pines guests enjoy discounts on guided trips with Gallatin River Guides​!) 

4. Water-Based Sports and Activities

Big Sky’s rivers and lakes are postcard-perfect and the site of some of the most refreshing summer fun around. Whether you’re chasing adrenaline or aiming for pure relaxation, there’s a water activity for everyone. Here are a few of our favorites:

  • Whitewater Rafting: If you’re craving a thrill, look no further than a whitewater rafting trip on the Gallatin River. Winding through a dramatic canyon just outside Big Sky, the Gallatin offers exhilarating class II-IV rapids with names like “Mad Mile” and “House Rock” that are sure to get your heart racing. Local outfitters like Geyser Whitewater Expeditions will get you geared up and guide you safely through the wild, splash-filled ride. It’s the perfect adventure for families, groups, or anyone looking to make unforgettable memories on the water.
  • Paddleboarding: For something a bit more mellow, try stand-up paddleboarding (SUP) on one of the area’s serene lakes. Lake Levinsky, located at the base of Big Sky Resort, is a favorite for calm waters and scenic surroundings. Or, for a more off-the-beaten-path experience, take a paddleboard out to Hyalite Reservoir, where you’ll glide across crystal-clear mountain water surrounded by pine forests and jagged peaks. It’s the perfect way to slow down and soak in Big Sky’s natural beauty.
  • River Tubing: If you’re in full vacation mode, floating the Madison River is the ultimate way to relax. Just south of Big Sky, this wide, lazy river is ideal for a slow, scenic drift with friends or family. Pack a cooler, bring a hat, and let the gentle current do the work. Warm sunshine, cool water, and stunning mountain views make this float one of Big Sky’s simplest summer pleasures.

5. Horseback Riding in Big Sky Country

No trip out West is complete without a classic horseback riding experience. Here in Big Sky country, you can channel your inner cowboy/cowgirl and explore the mountain trails the old-fashioned way…on horseback! Every summer, local outfitters like the legendary Jake’s Horses saddle up to give visitors a taste of Montana’s ranching heritage. 

There’s something magical about forging creek crossings and trotting through wildflower meadows atop a gentle, trail-wise horse. By the end of your ride, you’ll have great photos, a newfound appreciation for these beautiful animals, and a story or two to tell back home. Don’t forget to tip your hat and thank your trusty steed!

6. Take in Stunning Views: Choose Your Adventure

One of the greatest parts of summer in Big Sky is just how easy it is to be surrounded by awe-inspiring views. You don’t have to be a hardcore hiker or athlete to enjoy them, either—whether you’re riding a scenic lift, scaling a rock face, or stargazing from your deck, the sights are unforgettable. Here are a few ways to soak in Big Sky’s natural beauty from every angle.

  • Chairlift Rides: One of the simplest pleasures in Big Sky is just riding a chairlift in the summer—no skis required! Big Sky Resort keeps a few of its ski lifts running all summer long for sightseers and hikers. Hop on the Swift Current or Ramcharger lift, dangle your feet, and glide quietly above the treetops as breathtaking views open up all around you. Big Sky Resort even offers guided scenic lift tours, where a local expert rides up with you and points out interesting tidbits about the peaks, wildlife, and geology as you soak in the sights​. 
  • Lone Peak Expedition: For the ultimate panoramic thrill, consider the Lone Peak Expedition: a guided jeep and tram ride that whisks you to the 11,166-foot summit of Lone Peak, the highest overlook in Montana. From up there, on a clear day you can see across three states and even into Yellowstone​. 
  • Rock Climbing: If you’re looking for a hands-on way to connect with the landscape (and don’t mind a little adrenaline), rock climbing in Big Sky is an epic way to elevate your adventure—literally and figuratively. The area around Big Sky offers a variety of climbing experiences, from beginner-friendly crags to challenging alpine routes. One popular destination is Gallatin Canyon, just a short drive from town, where routes like “Scorched Earth” and “Sparerib” provide stellar climbing and even better views of the river below. Whether you’re bouldering, top roping, or sport climbing, local outfitters like Montana Alpine Guides offer guided climbs, gear rentals, and instruction for all levels. It’s a great way to try something new—or to push your skills to the next level in an unforgettable setting.
  • Stargazing: It’s no coincidence Montana is nicknamed “Big Sky Country.” The night skies here are phenomenal. With minimal light pollution in Big Sky, on a clear night you can see the Milky Way spilled across the sky like white fire. Consider spending an evening just kicking back on the deck of your vacation rental or driving out a few miles from the village for an impromptu astronomy night. (On certain summer nights, you might even catch meteor showers or the glow of the Northern Lights if you’re lucky!). 

7. Summer Events & Local Culture

If you’re looking to dive into the local community, Big Sky offers a range of eclectic events all summer long. If you time your visit right, you can join the locals for festivals, markets, and even rodeo thrills that add a special flavor to your trip. Here are a few summer events worth checking out:

  • Music in the Mountains: – Every Thursday evening all summer, Big Sky throws a free outdoor concert in Town Center Park. For over a decade, this has been Montana’s finest free music series, featuring up-and-coming bands as well as big-name artists in an incredible alpine amphitheater setting​. It’s family-friendly and BYO blanket/chairs. Grab a spot on the lawn, enjoy the tunes, and dance under the big sky!
  • Big Sky Farmers Market: On Wednesday nights from June through September, Town Center hosts a bustling farmers market (5–8 p.m.) with an array of local produce, art, crafts, and food trucks. Strolling the stalls, you can pick up fresh veggies, sample huckleberry jam, admire local artists’ work, and even catch some live music in the background​. It’s a perfect low-key evening to mingle with locals and savor Big Sky’s community spirit.
  • Big Sky PBR (Professional Bull Riding): For a dose of Wild West excitement, plan for the annual Big Sky PBR rodeo in July. This event has been crowned PBR’s “Event of the Year” multiple times, and it’s easy to see why. World-class bull riders and bulls converge on Big Sky for three nights of heart-stopping rodeo action​. The outdoor arena rocks with energy as cowboys attempt 8-second rides on raging bulls. Tickets can sell out quickly, but if you’re in town during PBR week, it’s an experience you won’t forget (think rodeo meets rock concert atmosphere).

Plan Your Big Sky Summer Getaway with Two Pines Properties

With so many Big Sky summer activities to choose from, you can craft the perfect mix of adventure and relaxation that suits your travel style. 

To make the most of it all, choose a comfortable home base where you can recharge each day. That’s where Two Pines Vacation Rentals shines. When you stay with Two Pines, you’re not just getting a luxury cabin or mountain condo with all the cozy amenities. You’re also tapping into a wealth of local knowledge and hospitality. 

Our team members are Big Sky locals who love our town, and we’re eager to help you experience it to the fullest. Plus, Two Pines properties are situated near all the action. Whether you want to be by the resort, on the river, or in the heart of Town Center, we have options that put you close to your must-do activities.

Book Your Big Sky Stay Today

Turn that Big Sky summer dream into reality. Book your stay with Two Pines Vacation Rentals, and let the mountains, rivers, and local Montana charm do the rest. We can’t wait to welcome you to Big Sky for the summer adventure of a lifetime!​

Big Sky Spring Events Guide: Where to Go & What to Do

Spring in Big Sky, Montana, is a season of transformation. As winter slowly gives way to warmer days, visitors can experience a perfect blend of late-season skiing, festive events, and emerging outdoor adventures. Whether you’re looking to carve the last turns of the ski season, soak up live music, or explore the backcountry as the snow melts, there’s no shortage of things to do. From March through May, here’s your go-to guide to the best Big Sky spring events.

Your Must-Visit Big Sky Spring Events

Spring Skiing & Resort Events

Spring skiing at Big Sky Resort is a dream. Warmer temps, longer days, and bluebird skies create prime conditions for soft snow and laid-back vibes. The resort often celebrates the end of the season with fun, festive events:

  • Pond Skim (April 26, 2025) – Watch costumed skiers and snowboarders attempt to skim across an icy pond at the base of the mountain. This crowd-favorite event features music, cheering spectators, and an electric atmosphere. Learn more about the Pond Skim event.
  • Spring Series: Music & Après (Every weekend in April) – Enjoy live performances and après-ski festivities in the Mountain Village Plaza. Dance into spring with DJ performances and soak in the vibrant atmosphere. Discover more about the Spring Series events.
  • Closing Weekend Celebrations (April 26-27, 2025) – The final days of the season bring ski costume contests, après-ski parties, and plenty of good vibes as locals and visitors say goodbye to winter. Details on Closing Weekend Celebrations.
  • Spring Lift Ticket Deals – Take advantage of special promotions in March and April that offer discounts on multi-day passes and lodging packages. Check out current lift ticket deals.

Live Music & Festivals

Big Sky’s spring calendar is packed with concerts, après-ski jams, and community festivals that bring the town to life:

Outdoor Adventures Beyond Skiing

Not a skier? No problem! Spring is the perfect time to explore Big Sky’s wilderness beyond the slopes:

  • Snowshoeing – Join a guided snowshoe tour at Big Sky Resort or explore trails like Ousel Falls, where melting snow reveals rushing waterfalls. Learn about snowshoeing opportunities.
  • Dog Sledding – Experience the thrill of mushing a team of huskies through snowy backcountry trails (offered through local outfitters like Spirit of the North). Discover dog sledding adventures.
  • Wildlife Watching & Yellowstone Tours – March and April are prime months for spotting grizzly bears emerging from hibernation, as well as bison, elk, and wolves in nearby Yellowstone National Park. Plan a Yellowstone tour.
  • Fly Fishing – Before the spring runoff, March and early April offer some of the best trout fishing of the year on the Gallatin and Madison Rivers. Learn about fly fishing in Big Sky.
  • Early-Season Hiking – By late April and May, trails like Beehive Basin and Lava Lake begin to open up, offering breathtaking mountain views with minimal crowds. Explore hiking trails.

Local Traditions & Community Events

Big Sky is more than just a resort—it’s a tight-knit mountain town with unique traditions that bring locals and visitors together:

  • Big Sky Shootout Film & Photo Festival (April 3, 2025) – A must-see for film lovers, the Big Sky Shootout is an annual community film and photography festival featuring locally made short films and stunning photo submissions. This creative celebration showcases the talents of Big Sky locals and the breathtaking landscapes they capture. Get Big Sky Shootout details.
  • Easter Sunrise Service & Egg Hunt (April 20, 2025) – Celebrate Easter in the mountains with a Sunrise Service on Andesite Mountain, followed by an Easter Egg Hunt at Big Sky Resort. Families can search for thousands of hidden eggs, with a golden egg prize up for grabs! Learn more about the Big Sky Resort Easter Egg Hunt.
  • Big Sky Swing Dance Nights (Recurring nights throughout the spring) – Put on your dancing shoes and experience a lively swing dance night in Big Sky! Local venues host these fun-filled evenings where beginners and experienced dancers alike can hit the dance floor, enjoy live swing music, and take part in an energetic community gathering. If you’ve never swing danced before, don’t worry—there are often beginner-friendly lessons to help you get started! Find swing dancing events.

Why Stay with Two Pines for Your Big Sky Spring Getaway?

After an action-packed day on the slopes or trails, you’ll want a comfortable, well-located retreat to relax in. Two Pines Properties offers the best selection of high-quality vacation rentals in Big Sky, with properties ranging from cozy ski-in/ski-out chalets to spacious lodges perfect for groups. Here’s why you should book with us:

  • Prime Locations – Stay just minutes from Big Sky Resort, Town Center, and top spring events. See your options today.
  • Locally Owned & Operated – Our team lives and works in Big Sky, providing guests with insider knowledge and personalized service. Meet the team.
  • On-Site Support – Need a last-minute restaurant recommendation or help with your rental? We’re just a call away.
  • Luxury & Comfort – Enjoy fully equipped kitchens, fireplaces, private hot tubs, and mountain views. Explore our selection of vacation rentals.

Book Your Spring Escape to Big Sky

With direct flights into Bozeman Yellowstone International Airport and an unbeatable lineup of spring events, outdoor adventures, and local traditions, now is the perfect time to visit Big Sky. Don’t wait—browse our vacation rentals today and make your spring getaway unforgettable!

Browse Two Pines Vacation Rentals in Big Sky

Direct Flights to Big Sky Montana: How to Actually Get Here Quickly

Big Sky, Montana: Premier Destination, Easy Access

Nestled in the heart of the Rocky Mountains, Big Sky, Montana, is a dream destination for outdoor enthusiasts, families looking to make one-of-a-kind memories, or anyone looking to escape the hustle of cityscapes. The activities and attractions are endless!

Whether you’re coming for world-class skiing in the winter, breathtaking hiking trails in the summer, or simply to soak in the natural beauty, you just want to get here as quickly and seamlessly as possible.

The good news? Traveling to Big Sky is easier than ever, thanks to convenient direct flights to Bozeman Yellowstone International Airport (BZN). It’s never been more simple to access your ideal mountain getaway.

Ready to start planning your escape to Big Sky? Keep reading to get all the details on direct flights to Big Sky, Montana, maximizing your access to BZN, and where to stay once you arrive.

Bozeman Yellowstone International Airport (BZN): The Gateway to Big Sky

While there is no airport located directly in Big Sky, BZN is known for its fast commute to Big Sky, friendly accommodations, and personable customer service. BZN is Montana’s busiest airport and the most convenient access point for eager travelers heading to Big Sky.

Located just 50 miles north of Big Sky, the airport offers a hassle-free arrival experience with quick access to transportation options. Whether you choose a rental car, private shuttle, or rideshare service, you can be in Big Sky and settling into your Two Pines Big Sky vacation rental in just under an hour.

Directions from Bozeman Yellowstone International Airport to Big Sky

Did you pick up a rental car and are wondering how to get to Big Sky from the BZN? It’s never been more simple. Here’s how to get here:

  • Exit the airport following Airway Blvd. and follow the roundabouts straight through onto Alaska Rd
  • Take a right on E Valley Center Rd
  • Take the next left onto Jackrabbit Ln
  • Continue onto US-191 S/Gallatin Rd
  • Turn right onto Lone Mountain Trail (The only traffic light after Four Corners)
  • Lone Mountain Trail passes through Big Sky’s Meadow Village & Town Center, before heading up to Big Sky Resort & Moonlight Basin.

Cities Offering Direct Flights to Bozeman

No matter where you’re flying from, there’s a good chance you can get to Big Sky with one simple non-stop flight. Bozeman Yellowstone International Airport offers non-stop flights from many major U.S. cities, making it easier than ever to plan your trip with a click of a button.

Here are some of the cities offering direct flights to BZN:

  • Atlanta, GA (ATL)
  • Boise, ID (BOI)
  • Boston, MA (BOS)
  • Chicago, IL (ORD – MDW)
  • Charlotte, NC (CLT)
  • Dallas/Fort Worth, TX (DFW – DAL)
  • Denver, CO (DEN)
  • Detroit, MI (DTW)
  • Houston, TX (LAH)
  • Las Vegas, NV (LAS)
  • Los Angeles, CA (LAX)
  • Minneapolis/St. Paul, MN (MSP)
  • Nashville, TN (BNA)
  • New York, NY (LGA – JFK)
  • Phoenix/Mesa, AZ (AZA)
  • Portland, OR (PDX)
  • Salt Lake City, UT (SLC)
  • San Diego, CA (SAN)
  • San Francisco, CA (SFO)
  • Seattle/Tacoma, WA (SEA)
  • Washington D.C., VA (IAD)

Note: Flight availability may vary seasonally. Always check with airlines for the latest schedules. If you want to learn more about direct flight routes to Bozeman, MT, visit the Bozeman Yellowstone International Airport’s Airline and Flight Information page. 

Tips for Booking Direct Flights to Bozeman

Want to lock in the best deal and a stress-free travel experience? Here are some expert tips:

  • Use Flight Search Engines: Websites like Google Flights, Skyscanner, and Kayak allow you to filter by direct flights, making your search faster and more efficient.
  • Book Early: Flights to Big Sky, Montana, can fill up quickly—especially during ski season and summer months. Book at least 2-3 months in advance for the best rates.
  • Be Flexible: If your dates are flexible, use fare comparison tools to find the cheapest days to fly. Mid-week flights tend to be more affordable than weekend departures.

Enhance Your Stay in Big Sky with Two Pines 

Once your flight is booked, it’s time to choose the perfect place to stay. So why not choose the best, most comfortable option? 

With consistent 5-star reviews, Two Pines Vacation Rentals offers top-tier accommodations in Big Sky, ensuring your trip is as enjoyable as it is unforgettable. From cozy ski cabins for a romantic getaway to spacious alpine lodges with rooms for every family member, we offer a range of lodging options to fit your dream vacation. 

Why Choose Two Pines Big Sky Vacation Rentals?

Choosing locally-owned vacation rentals for your Big Sky trip connects you to the heart of this truly unique Montana community. With Two Pines Properties, you not only get the largest selection of high-quality Big Sky vacation rentals to choose from. You get a boots-on-the-ground team who lives, breathes, and loves the Big Sky community.

What Makes Us Different?

  • A Team that Genuinely Cares – From hand-written welcome cards to personalized recommendations, we ensure every guest feels at home.
  • Locally Owned and Operated – Our team lives and works in Big Sky, so we’re always nearby when you need assistance.
  • On-Site Support – Whether you need help with a rental issue or a last-minute dinner reservation, we’re just a call away.
  • Insider Knowledge – Get expert local recommendations for hidden gems, the best trails, and the most authentic Montana experiences.

What We Offer in Our Vacation Rentals

  • Diverse Rental Options – Whether you’re seeking a cozy cabin for two or a spacious home for a large family gathering, we have the perfect property for your needs.
  • Luxury Meets Comfort – Enjoy modern amenities, high-end furnishings, and breathtaking mountain views that make your stay truly special.
  • Prime Locations – From ski-in/ski-out properties to secluded retreats surrounded by nature, our rentals are ideally situated to give you the best Big Sky experience.
  • Fully Equipped Homes – Many of our rentals come with amenities like fully stocked kitchens, fireplaces, private hot tubs, and everything else you need for a memorable stay.

Book Your Stay for Big Sky, Montana Today

With direct flights making Big Sky more accessible than ever, there’s never been a better time to plan your trip. Whether you’re visiting for an action-packed adventure or a relaxing getaway, Two Pines Properties has the perfect home for your stay.

Ready to book your perfect stay? Browse our vacation rentals and start planning your Big Sky adventure today!

Here’s Why Two Pines’ Big Sky Vacation Rentals Outshine Big Sky Hotels

Big Sky is the place that stays in your heart and memories long after you leave. Towering snow-capped peaks, fresh mountain air, and endless outdoor adventures make it a dream destination for skiers, hikers, and anyone looking to escape into nature. 

But where you stay can shape your entire trip. 

If you’re looking for places to stay in Big Sky, know that a hotel just won’t live up to the hype of your mountain getaway. Big Sky hotels might seem like the easy choice, but they can’t offer what local vacation rentals offer a level of comfort, privacy, and local charm that hotels simply can’t match. 

Experience the Big Sky state the way it’s meant to be. Here’s why Two Pines Properties’ Big Sky vacation rentals are the best choice for any Montana adventure.

5 Ways Our Vacation Rentals in Big Sky Surpass Hotels

1. The Space You Need, The Comfort You Deserve

A hotel room might work for a quick overnight stay. But if you’re spending several days in Big Sky, space matters. Most hotels offer a standard one-room layout with a bed, a small sitting area, and a bathroom—functional but limiting. For couples, this setup may be fine, but for families or groups, it quickly becomes cramped. If you’ve ever tried to relax in a hotel room while someone else is taking a conference call, kids are playing on the floor, and ski gear is piled up in the corner, you know how quickly space can feel tight.

Vacation rentals offer an entirely different experience. Instead of being confined to a single room, you get multiple bedrooms, spacious living areas, and often a private deck or patio to enjoy the stunning mountain views. Having separate spaces means everyone can unwind in their own way—kids can play in one room, while adults relax in another. Full kitchens allow for easy meal prep, while cozy fireplaces and plush seating make it easy to settle in after a long day on the slopes.

Beyond functionality, space creates comfort. Imagine coming back from a day of skiing and stretching out on a sectional couch by the fireplace, rather than squeezing into a desk chair or propping up pillows against a hotel headboard. The extra space in a vacation rental transforms your stay from simply a place to sleep into a place where you can truly relax and enjoy your time in Big Sky.

2. Privacy & Peace: Escape the Crowds

Hotels are designed for efficiency, not tranquility. Hallways echo with the sounds of doors slamming, and conversations carry through thin walls. The constant shuffle of guests moving in and out can make it hard to truly relax. 

A vacation rental offers a completely different experience. Instead of navigating crowded hallways and busy lobbies, you can step straight into your private retreat. There’s no need to worry about noisy neighbors or unwanted disturbances—you have the space to truly unwind. Many vacation rentals in Big Sky are tucked away in peaceful residential areas or nestled into the mountainside, offering stunning views and a sense of seclusion that hotels simply can’t match.

Privacy extends beyond just avoiding noise. In a vacation rental, you don’t have to share amenities like hot tubs, balconies, or outdoor seating areas with strangers. You can enjoy your morning coffee in your pajamas on a private deck, soak in a hot tub under the stars without worrying about other guests, and come and go as you please without bumping into housekeeping staff or large tour groups.

Whether you’re traveling solo, as a couple, or with a group, the ability to fully relax and enjoy your own space makes a vacation rental the superior choice for those seeking peace and quiet in Big Sky.

3. Soak Up the Local Experience

Big Sky can easily be impacted by the place where you stay. Hotels often offer a generic, one-size-fits-all experience, with little connection to the surrounding area. The recommendations you receive at the front desk are usually the same mainstream tourist spots listed in every guidebook, and interactions with staff can feel transactional rather than personal.

A vacation rental connects you to the destination in a way that hotels can’t. When you stay with a locally owned rental company like Two Pines, you’re tapping into genuine local knowledge. Instead of generic suggestions, you get curated recommendations from people who live in Big Sky year-round. Maybe it’s a lesser-known hiking trail with breathtaking views or a family-owned restaurant that serves the best bison burger in town. These small details transform your trip into a more immersive and memorable experience.

Staying in a vacation rental also allows you to experience Big Sky in a way that feels more authentic. Rather than being confined to a commercialized hotel district, you can stay in a charming mountain home, a modern ski-in/ski-out condo, or a secluded cabin surrounded by nature. For travelers who want more than just sightseeing, vacation rentals provide a deeper connection to the destination. 

4. Flexibility & Convenience: No Rigid Schedules

Hotels come with schedules, and that means your vacation often has to adjust to their rules. Breakfast service ends early, housekeeping knocks at inconvenient times, and check-in and check-out times are often strict.

Vacation rentals offer the kind of flexibility that makes your trip feel like a true getaway. Instead of planning around hotel policies, you set your own schedule. Wake up when you want, cook meals on your own time, and enjoy a laid-back pace without worrying about service restrictions.

Having a full kitchen is a game-changer. Instead of eating out for every meal, you can prepare breakfast before heading to the mountain, pack a lunch for a scenic picnic, or cook a hearty dinner after a long day of adventure. 

This flexibility also means a smoother travel experience. Many vacation rentals offer self-check-in, so there’s no need to rush to a front desk before it closes. A vacation rental gives you the freedom to experience Big Sky on your own terms—without the constraints of hotel rules and schedules.

5. True Value: More for Your Money

Hotels may seem convenient, but when you break down the costs, they often don’t provide the best value. A standard hotel room typically offers little more than a bed and bathroom. Additional amenities—parking, Wi-Fi, breakfast, and even access to certain hotel facilities—often come with extra fees. 

Vacation rentals give you more for your money. Instead of a small hotel room, you get an entire home or condo, complete with a kitchen, living space, and multiple bedrooms. This is especially valuable for families and groups, where renting a single vacation home can be far more cost-effective than booking multiple hotel rooms.

Beyond space, vacation rentals include perks that hotels charge extra for. Many come with private hot tubs, stunning mountain views, game rooms, and cozy fireplaces—all included in the rental price. Having a full kitchen also means you can save money on dining out, giving you the option to enjoy home-cooked meals instead of relying on expensive restaurants for every meal.

Why Two Pines? The Best Vacation Rentals in Big Sky

If you’re convinced that a vacation rental is the way to go, the next step is finding the right one. Two Pines Properties offers the largest selection of high-quality vacation rentals in Big Sky, all managed by a local team that’s here to make your stay seamless. 

As a locally owned and operated company, Two Pines provides personalized service from people who live in Big Sky and genuinely care about your experience. Every rental is carefully curated, from cozy cabins to luxurious mountain homes, ensuring that every guest finds the perfect fit.

Unlike corporate rental companies that manage properties from afar, Two Pines has a dedicated on-the-ground team to assist with anything you need. Whether it’s a mid-stay request, an unexpected issue, or a local recommendation, they’re always nearby to help. Hotels can offer a place to sleep, but Two Pines offers an experience.

Book Your Stay, Experience the Big Sky Way

Hotels can offer a place to sleep, but Two Pines offers an experience. Two Pines Properties’ Big Sky vacation rentals give you more space, more privacy, and a real connection to a one-of-a-kind destination. With Two Pines, you’ll have everything you need to experience Big Sky the right way—on your terms, with all the comforts of home.

Ready to book your perfect stay? Browse our vacation rentals and start planning your Big Sky adventure today!

Winter Wonderland Awaits: Can’t-Miss Big Sky Winter Events

Snow encrusted peaks and squeals of delight from the ski runs. Twinkling fairy lights from frosted pine branches and cozy storefronts with smiling faces welcoming you home. Crisp mountain breezes and the smokey tang of a woodburning fireplace in the air. Sounds like a scene from a Hallmark film or a holiday card, right?

What if we told you that you could experience this and so much more in real life? 

These scenes are just whispers of the vibrant winter wonderland known as Big Sky, Montana.

During the snowy months from December to February (and often beyond), Big Sky is the “it” place to be to enjoy the picture-perfect winter. A tiny mountain town nestled just north of Yellowstone National Park, Big Sky is an exclusive hub for solo travelers and families seeking the ideal winter getaway. From snow-filled adventures and cozy nights in to quirky local traditions and classic winter activities, there are Big Sky winter events for all ages to enjoy. 

Looking for a winter adventure or maybe a relaxing snowscape to gaze at as you cozily sip hot cocoa? Big Sky can offer that and so much more! Keep reading to view our exclusive guide to winter activities in Big Sky. If you’re looking for the perfect base to call “home” while your exploring Big Sky’s many events, Two Pines Properties has the best local property rentals available. 

The Best Big Sky Winter Events 

Big Sky, Montana, comes alive in the winter months, offering a mix of festive celebrations, thrilling competitions, and unique cultural experiences that make it a must-visit destination. From late December through February, the beautiful town and surrounding areas host an array of events that showcase the spirit of this mountain community. Whether you’re looking to revel in holiday cheer, enjoy the thrill of winter sports, or take in world-class performances, there’s no shortage of ways to make your Big Sky winter getaway unforgettable.

We’ll explore the magic of Big Sky’s holiday events, the excitement of outdoor winter activities, and other fun-filled experiences waiting for you in this snowy paradise.

Big Sky Holiday Events

Riding your sleigh into Big Sky for the holidays? You’ve chosen the perfect place to experience the merriest time of year! Big Sky offers a wide range of holiday activities to help you make the season bright and ring in the new year. Let’s take a peek at the presents Big Sky has to offer for holiday activities:

1. Enchanted Forest Lighting Ceremony

Kick off the holiday season with the illumination of the Enchanted Forest on Andesite Mountain. This special lighting ceremony marks the opening of a winter wonderland, inviting guests to explore beautifully lit trails and festive decorations. 

When: December 11, 2024
Learn more: Bigskyresort.com/events/enchanted-forest-lighting-ceremony 

2. Christmas Stroll

Join the Big Sky community for the annual Christmas Stroll, a cherished tradition featuring tree lighting ceremonies, photos with Santa, illuminated cross-country ski and fat bike trails, sleigh rides, classic holiday films, carolers, and fireworks. The festivities span multiple locations—including the Big Sky Town Center, Nordic Center, and Meadow Village—so you can experience the best and brightest of Big Sky in a single night.  

When: : December 13-15, 2024
Learn more: Bigskyresort.com/events/christmas/christmas-stroll 

3. The Nutcracker Ballet

Experience the timeless magic of “The Nutcracker” performed by the Montana Ballet Company at the Warren Miller Performing Arts Center. Set to Tchaikovsky’s beloved score, this production is a holiday favorite for all ages. 

When: December 15, 2024
Learn more: Warrenmillerpac.org/event/nutcracker-montana-ballet/ 

4. Reindeer Visits

Meet Santa’s delightful reindeer at the Mountain Village Plaza. Learn about these majestic creatures before they journey back to the North Pole. 

When: December 20 and 23, 2024, 5:00pm to 7:00pm
Learn more: Bigskyresort.com/events/christmas/reindeer 

5. Pictures with Santa Claus

Capture cherished memories with Santa at the Mountain Village Plaza. Bring your wishlist and enjoy a festive photo opportunity. 

When: December 21 and 23, 2024, between 12:00 and 4:00 pm
Learn more: Bigskyresort.com/events/christmas/pictures-with-santa 

6. Holiday Cookie Decorating Class

Unleash your creativity at an all-ages cookie decorating class in the Cheyenne Room, Huntley Lodge. Registration is required for this festive activity. 

When: December 21 and 28, 2024, 4:00 pm to 5:30 pm

Learn more: Bigskyresort.com/events/christmas/cookie-decorating-dec-21 

7. Holiday Cocktail Creation

Join expert mixologists for a holiday cocktail creation class, where you’ll learn to craft festive beverages. This class is for guests 21 and over.

When: December 22, 27, and 30, 2024, 8:00 pm to 9:00 pm
Learn more: Bigskyresort.com/events/christmas/holiday-cocktail-class-dec-27 

8. Holiday Trivia

Test your festive knowledge at Westward Social. Enjoy a spirited game of trivia alongside delicious dinner and drinks. 

When: December 23, 26, 29, and January 1, 2025
Learn more: Bigskyresort.com/events/christmas/holiday-trivia 

9. Fireworks & Torchlight Parade

Marvel at a stream of lights descending Andesite Mountain during the torchlight parade, followed by a spectacular fireworks display visible from Mountain Village. 

When: on December 24, 2024, 8:30 pm
Learn more: Bigskyresort.com/events/christmas/fireworks-and-torchlight-parade 

10. Skiing with Santa

Hit the slopes with Santa Claus, Mrs. Claus, and the elves! Catch them on the mountain and in the base areas, adding a festive touch to your skiing experience. 

When: December 24 and 25, 2024
Learn more: Bigskyresort.com/events/christmas/skiing-with-santa 

11. New Year’s Eve Fireworks

Ring in the New Year with a dazzling fireworks display at Big Sky Resort. The festivities include gourmet dining, live music, and family-friendly activities, culminating in a vibrant celebration. 

When: December 31, 2024, 9:00 pm
Learn more: Bigskyresort.com/events/new-years-eve/fireworks 

12. New Year’s Eve Party

Dance the night away at Montana Jack’s New Year’s Eve Party. Enjoy music, dancing, and celebration as we bid farewell to 2024 and welcome 2025. This event is for guests aged 21 and over; tickets are required.

When: December 31, 2024, 9:30 pm
Learn more: Bigskyresort.com/events/new-years-eve/new-years-eve-party 

13. New Year’s Eve Masquerade Ball

Celebrate in style at The Waypoint’s Masquerade Ball with live music, drink specials, and a champagne toast. Dress to impress for the Best Dressed Contest!

When: December 31, 2024
Learn more: Visitbigsky.com/event/nye-masquerade-ball/1522/ 

Big Sky Winter Outdoor Activities 

In the winter, Big Sky transforms into a playground of wonder, offering an array of activities that immerse you in its stunning snowy landscape. Whether you’re carving down world-class ski slopes, exploring peaceful snow-covered trails, or experiencing the thrill of dogsledding or snowmobiling, every moment in Big Sky is a chance to create unforgettable memories.

1. Snow Sports 

  • Skiing & Snowboarding: Experience the “Biggest Skiing in America” at Big Sky Resort, boasting over 5,850 acres of skiable terrain suitable for all skill levels. Whether you’re a novice or an expert, the resort offers diverse runs to match your abilities. 

    Learn more: Bigskyresort.com 
  • Skiing & Snowboarding Lessons: Enhance your skills with professional instruction available for both skiing and snowboarding, ensuring a safe and enjoyable experience for all ages. 

    Learn more: Bigskyresort.com/lessons 
  • Nordic Skiing & Snowshoeing: Lone Mountain Ranch boasts 80 kilometers of world-renowned groomed cross-country ski trails, offering an unforgettable Nordic skiing experience. Voted the #1 Nordic Ski Resort in North America by Cross Country Skier magazine, the ranch caters to every type of skier and snowshoer.

    Learn more: Lonemountainranch.com/perfect-ski-trip-big-sky/ 

2. Outdoor Adventures

  • Snowmobiling: Embark on thrilling snowmobile tours through the Gallatin Canyon or venture into Yellowstone National Park to witness iconic landmarks like Old Faithful. These guided adventures cater to both beginners and seasoned riders, offering an exhilarating way to explore the winter landscape. 

    When: Available throughout the winter months. Check listings for availability.
    Learn more: Backcountry-adventures.com/ 
  • Dogsledding: Your guides will provide hands-on instruction and expert tips, allowing you to experience the exhilarating thrill of driving your own sled dog team. Picture yourself gliding through a snowy wonderland, surrounded by Montana’s majestic mountains, as a team of spirited Alaskan huskies leads the way. Their high spirits and lovable personalities are sure to capture your heart in no time.

    When: Available throughout the winter months. Check listing for availability.
    Learn more: Huskypower.com 
  • Snowcoach Tours: Discover the winter wonders of Yellowstone National Park aboard a heated snowcoach, offering comfortable access to geothermal features and wildlife sightings amidst the snowy backdrop. These tours are ideal for families and groups seeking a relaxed yet immersive experience.

    When: Available throughout the winter months. Check listing for availability. 
    Learn more: Backcountry-adventures.com

Local-Favorite Winter Events

1. Warren Miller’s Performance Arts Center

MPAC hosts a diverse lineup of world-class performances throughout the winter season, including music, theater, and dance, enriching Big Sky’s cultural scene. One of the amazing events they host is International Guitar Night. Scheduled for February 20, 2025, this event features a captivating evening with renowned acoustic guitarists from around the globe, offering a unique musical experience.

Learn more: Warrenmillerpac.org/ 

2. Best In The West Showdown

Witness the excitement of skijoring—a unique sport where a skier is pulled by a horse through a course of jumps and obstacles. This family-friendly event also features live entertainment and festivities, capturing the adventurous spirit of Big Sky.

When: February 8-9, 2025
Learn more: Bigskytowncenter.com/annual-events/ 

3. Winter Farmers Market

Explore local crafts, produce, and artisanal goods at the Big Sky Winter Farmers Market. It’s a delightful way to engage with the community and find unique souvenirs. 

When: Available throughout the winter months. Check listing for availability.
Learn more: Bigskytowncenter.com/farmers-market/ 

4. Country Dance Nights

Put on your dancing boots and join the locals for an evening of country dancing. These events are filled with lively music and are a fantastic way to experience Big Sky’s vibrant community spirit.

When: Recurring weekly on Wednesday
Learn more: Visitbigsky.com/event/country-dance-nights/1185/ 

5. Montana Dinner Yurt

Discover the enchantment of dining under Montana’s Big Sky at the Montana Dinner Yurt. Begin your adventure with an exciting ride through the picturesque backcountry in a rugged army truck, leading to a cozy yurt nestled amidst breathtaking views. Inside, indulge in a hearty, three-course meal crafted with care and bursting with flavor. Whether you’re marking a special occasion or simply looking for a one-of-a-kind dining experience, a night at the Montana Dinner Yurt promises unforgettable moments and cherished memories.

When: Availability throughout the winter months. Check listing for reservations.
Learn more: Bigskyyurt.com 

6. Sleigh Ride Dinner

Take a magical 20-minute sleigh ride through snowy trails under a sparkling night sky to the historic North Fork Cabin. Inside, savor a three-course, family-style meal of mouthwatering dishes, such as \ prime rib slow-cooked on a century-old stove, mashed potatoes, and huckleberry cobbler. Cowboy singer-storytellers add charm with songs and tales, creating an unforgettable evening.

When: December through April
Learn more: Lonemountainranch.com/sleigh-ride-dinner/ 

Why Stay with Two Pines Properties

When it comes to experiencing the best of Big Sky in winter, Two Pines Properties is your trusted partner. Our vacation rentals are strategically located to provide easy access to the area’s most exciting winter activities and events, from the thrill of skijoring to serene snowshoeing trails. Whether you’re here for family fun, a romantic getaway, or an adventurous retreat, our homes put you right in the heart of the action.

What sets Two Pines apart is our personalized service and local expertise. We’re more than hosts. We’re your local guides, ready to help craft a seamless and unforgettable winter itinerary. Our team’s insider knowledge ensures you’ll discover hidden gems and make the most of your time in Big Sky.

After a day filled with snowy adventures, return to the comfort and warmth of a Two Pines property. From cozy fireplaces and luxurious hot tubs to fully equipped kitchens for family meals, our amenities are designed for relaxation and connection. Here, you’ll find all the comforts of home—and then some.

Plan Your Winter Escape with Two Pines

Big Sky is calling, and winter is the perfect time to answer. With its dazzling array of events, world-class outdoor activities, and breathtaking mountain scenery, this destination offers something for everyone. Two Pines Properties is your key to experiencing it all with ease and style.

Ready to experience the best of Big Sky this winter? Explore our vacation rentals today and start planning your unforgettable getaway!

Big Sky Vacation Rentals: Why Choosing Local Makes a Difference

“Choose Local” goes deeper than a phrase you hear during Black Friday or see on a storefront sticker. “Choose Local” means investing in a one-of-a-kind experience you can only find in a local community, one steeped in tradition, culture, and community. So if you’re planning a Big Sky getaway, the choice of where you stay and who’s managing your trip matters more than you think.

Choosing locally-owned vacation rentals for your Big Sky trip connects you to the heart of this truly unique Montana community. With Two Pines Properties, you not only get the largest selection of high-quality Big Sky vacation rentals to choose from. You get a boots-on-the-ground team who lives, breathes, and loves the Big Sky community. 

That means you get a better trip experience. Period.

If you want to see the difference locally-owned vacation rentals can make for your trip to Big Sky, keep reading and enjoy the adventure! Ready to book your stay in Big Sky? Browse through our available vacation rentals in Big Sky today.

What Does it Mean to be a “Locally-Owned Business?”

Being locally owned isn’t only about having a physical presence in Big Sky. It’s about being part of the community. So when we say we’re a locally owned business, we’re not talking about being a business that started in Montana but is now so large that it has no ties to the local community. We’re the real deal. 

Two Pines Properties is Big Sky’s largest locally-owned and operated rental company with team members who live, work, and thrive in this community. Our co-owners Wes and Alex Hoecker are proud Big Sky residents who brave through our infamous snowstorms to pen hand-written cards to our guests (Watch this video if you don’t believe us). Our deep roots in the community allow us to offer a truly personalized experience, ensuring that every guest feels like part of our Big Sky family.

How We Live Up to the “Locally-Owned” Label

Our local connection enables our team to provide a level of care and attention to guests that larger, corporate competitors simply can’t match. From offering insider tips on the best trails in Yellowstone National Park to recommending family-friendly activities in and around the Big Sky area, our team members’ local expertise ensures every guest has a memorable stay, every rental is comfortable, and every reservation goes smoothly. So when you choose Two Pines, you’re not just renting a property—you’re gaining a trusted friend and local guide to all that Big Sky has to offer.

How You Benefit From Local Big Sky Vacation Rentals

To put it simply, staying with a locally owned vacation rental company means a better, more personalized Big Sky experience for you. At Two Pines Properties, our deep connection to the Big Sky community allows us to offer a level of care and service that sets us apart from corporate competitors. Our team is more than property managers. We’re your neighbors, guides, and trusted hosts who are here to make your trip exceptional in every way. Here’s what you get when you choose local vacation rentals with Two Pines Properties:

1. A Team that Genuinely Cares

In Montana, hospitality is a way of life, and our team embodies that spirit. From the moment you book with Two Pines, you’ll feel the difference. We’re here to answer your questions, provide guidance, and ensure every aspect of your trip is seamless. 

Whether it’s delivering firewood during a snowstorm or helping you book a last-minute reservation at a local favorite restaurant, we enjoy making your time in Big Sky unforgettable. It’s the little moments, like providing thoughtful suggestions tailored to your interests, that make your trip feel as welcoming as the community we call home.

2. No Long-Distance Relationships

Unlike big corporate rental companies, we don’t manage properties from hundreds of miles away. Our team lives and works right here in Big Sky, breathing the same crisp mountain air and enjoying the same breathtaking views that brought you here. This means we’re steeped in local knowledge and deeply connected to the community.

Because we’re local, we can respond quickly to your needs—whether it’s fixing a minor issue in your rental, recommending a dinner spot that fits your vibe, or sharing real-time updates on weather and conditions. You’re never left waiting for an answer from a distant call center.

3. Available On-Site Support

Things can come up while traveling, and having on-site support makes all the difference. At Two Pines, we’re here when you need us. Maybe you need help figuring out how to use the hot tub after a long day of skiing, or perhaps you’re curious about where to rent snowshoes for tomorrow’s adventure. Whatever the need, our team is just a call or a short drive away to ensure everything goes smoothly.

This on-site presence gives you peace of mind. If something unexpected happens—a power outage, a lost key, or even just needing a few extra blankets—you’re not left scrambling for help. Our team is here to ensure your vacation stays stress-free and enjoyable.

4. You Get the Insider Scoop

One of the best parts of staying with a locally owned company is access to the kind of insider knowledge you can’t get from a quick Google search. We love sharing our favorite Big Sky secrets, like the best time to hit the slopes for fewer crowds, the quietest trails for a morning snowshoe, or the coziest spot for après-ski cocktails. 

We love helping you discover the hidden gems that make Big Sky feel like home. Think tucked-away cafes, family-owned restaurants, or local events that give you a true taste of Montana culture. These personalized tips help you experience Big Sky in a way that feels authentic and unique.

Book Your Stay, Experience the Big Sky Way

Your Big Sky adventure deserves the personal touch that only a locally-owned company provides. The Twin Pines team truly loves and lives in this community, so we’re excited to share the joys of our community with you.

Experience Big Sky the way it’s meant to be. Browse our vacation rentals and book your stay with Two Pines Properties today!