Two Pines Vacation Rentals

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Big Sky Montana Vacation Rentals

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!

Flying or Driving | How to Get to Big Sky

Big Sky is known for being an outdoor enthusiast’s playground, and for good reason. From world-class skiing once the resort opens at the end of November to being the perfect base camp for a Yellowstone vacation, this popular Montana town is surrounded by adventure. However, before you can enjoy all the fun, you need to take care of a couple of logistical items. One is reserving your rental from Two Pines Properties. The other is figuring out how you’re going to get to Big Sky.

Option 1: Flying

If you’re traveling from afar, your best bet is to catch a flight to Big Sky. The Bozeman Yellowstone International Airport is less than 45 minutes from town. Depending on the time of year, there are several nationwide direct flights, so you don’t have to spend all day in airports. Another option is the West Yellowstone Airport, which has seasonal flights from Denver and Salt Lake City. 

If you are flying, there are plenty of shuttle services that can get you to and from the airport, including Skyline Bus and Karst Stage. The airport also has several rental car options for those looking to have a car with them for the duration of their vacation. Guests at our Big Sky cabins can enjoy a discount code for a car from Explore Rentals.

Option 2: Driving

Driving to Big Sky is a great way to enjoy a vacation within your vacation. No matter how long of a drive you have, there are sure to be attractions to explore along the way. Take your time to stop at some of these roadside spots to add a bit of extra fun to your vacation. Before heading out, be sure you have a car emergency kit packed, snacks ready, and your favorite playlist queued up.

Turn to Two Pines for Your Big Sky Rental Needs

The living area of a vacation rental to relax in after navigating how to get to Big Sky.

No matter how you choose to get to Big Sky, rest easy knowing you have a relaxing place to unwind after your journey. At Two Pines, our well-appointed Big Sky rentals come in a range of sizes and styles. From luxurious cabins to modern condos, all our properties have all the comforts of home. This means whether you are planning a trip for two or a getaway with all your friends, we have the place for you. 

As you browse our accommodations, look for extra amenities designed to enhance your stay. These features can include hot tubs, a balcony, ski-in/ski-out access, and more. We even have pet-friendly rentals! For more information on one of our Big Sky rentals or to learn more about special offers, call 406-995-2299.

Why Call Big Sky Home on a Yellowstone National Park Vacation

One thing that can make or break any vacation is where you call home. This is especially true for anyone planning a vacation to Yellowstone National Park. This popular natural attraction is filled with endless adventure. Given its size, there are several towns to choose from when picking your base camp, and Big Sky should be at the top of your list. The local team at Two Pines Properties has first-hand knowledge of why our Montana town is your perfect option. Keep reading to learn more.

Variety of Area Amenities

Having a relaxing vacation rental to call home is only one piece of the puzzle regarding your Yellowstone vacation. After a long day of exploring the 2.2 million-acre park, you’re sure to have worked up an appetite. Luckily, Big Sky is home to countless restaurants to choose from, like Horn & Cantle, Buck’s T-4, and Ousel & Spur Pizza Co. You can also stop by a local grocery store like Roxy’s Market & Cafe to stock up on things to make a delicious meal in your Big Sky rental. If you’re looking to soothe your sore muscles, visit Solace Spa & Recovery Lounge or Raydient Bodywork for a massage. 

Proximity to Park Entrances

Big Sky is only about 20 minutes from the park’s west boundary. However, it takes about an hour to reach the gate where you can purchase an entry pass. While this may seem like a bit of a drive, the stunning views make the journey worth it. This gives you plenty of time to map out your hikes and any other activities you’re hoping to enjoy. One thing we don’t recommend waiting to book on the drive is your outing with Backcountry Safaris, which offers both half-day and full-day excursions. You’ll want to reserve your spot on a tour around the same time you reserve your rental.

Variety of Big Sky Vacation Rentals to Choose From

The hot tub at a Big Sky rental to relax in on a Yellowstone National Park vacation.

One of the biggest reasons to make Big Sky your base camp is the incredible selection of rentals from Two Pines. Our inventory of well-appointed vacation properties has it all. Whether you’re looking for a cozy condo, a charming townhome, or a spacious home, we have just the place for you.

While all of our rentals have the comforts of home, one might fit your Yellowstone National Park vacation better than the others. Take your time browsing our offerings to find the one that meets all your wants and needs. We highly recommend choosing a rental with a hot tub, perfect for relaxing after going on a guided hike with Backcountry Safaris. For help reserving your Big Sky vacation rental or to learn about special offers, call 406-995-2299.

Plan Your Visit to Big Sky PBR | Tickets, Schedules, & More

While Big Sky is known for its endless outdoor activities, it’s also home to a jam-packed calendar of events. From checking out incredible music festivals to trying delicious bites at a food festival, there’s something for everyone. One of the year’s most anticipated events is the Big Sky PBR. To help you make the most of your trip to this annual event, the team at Two Pines Properties has put together a guide with important information.

An Overview of the Schedule

For three days in July, some of the world’s best bull riders make their way to Big Sky for the annual Big Sky PRB. However, the fun isn’t limited to three days of riding. The yearly event features things to do that the whole community can enjoy.

Things kick off with the Community Rodeo and Community Street Dance. There’s also Bingo Night, a golf tournament, and more, all leading up to the highly anticipated bull riding nights. 

There are three different nights of riding, with the championship night taking place on Saturday night. We recommend getting to the Big Sky Events Arena early to stock up on snacks and drinks. 

What to Know about Attending the Event

There are several different ticket options available, ranging from general admission to Golden Buckle VIP. If tickets are sold out, you can sign up for the waitlist. 

Another great way to attend the rodeo is to volunteer with BigSkySNO, which is dedicated to protecting and preserving the Big Sky community through sustainability and environmental initiatives. To learn more about their volunteer opportunities at this Big Sky event, fill out their contact form.

When you arrive at the venue, there is designated parking via passes sold at the gate on a first-come, first-served basis. You can access the lot on Aspen Leaf Drive. 

For more answers to common questions, visit the PBR’s FAQ page.

Reserve Your Big Sky Rental Today

The living area of a vacation rental to stay at when attending the Big Sky PBR.

Given the popularity of the Big Sky PBR, it’s important you don’t wait to reserve your Big Sky vacation rental. For some of the best properties in town, turn to Two Pines. The goal at our locally owned and operated company is to bring you vacation rentals that exceed your expectations. This means looking for homes and condos in a range of sizes and price points found throughout town. 

We know it takes more than a relaxing place to call home to have the best stay possible. We’ve worked with local partners to provide our guests with incredible discounts. To learn more about our Two Pines Perks or special offers, call 406-995-2299.

An Unforgettable Montana Spring Break to Big Sky

Big Sky is the ideal destination for any family looking to create long-lasting memories. While the popular town attracts countless visitors during the winter months, there is no bad time of year to visit. Plan your visit to Big Sky with Two Pines Properties for a fun and unique Montana spring break escape.

No matter the age of your children, there’s no shortage of things to do in and around Big Sky that everyone will love. While this spring is sometimes referred to as the mud season, you can still get out and enjoy some of the top activities Big Sky is known for. Keep reading to learn more about what to include on your itinerary.

5 Things to Do in Big Sky on Spring Break

  1. Get in some last runs down the mountain. The mountain is usually open through the end of April, so you have plenty of time for end-of-season skiing. We recommend purchasing your lift tickets early.
  2. Book a spot on a wildlife tour to see what creatures you can spot in Yellowstone National Park. Backcountry Safaris offers full-day and half-day tours that take you around the park.
  3. If you aren’t afraid to get a little muddy, go biking in Yellowstone. Because the roads are still closed to cars, you’ll have the roadways to yourself.
  4. Try your hand at flyfishing on an excursion with Gallatin River Guides. Since 1984, this guide service has been offering year-round trips in world-class trout streams.
  5. See what you can find on a shopping spree. Both Big Sky Resort and Big Sky Center are home to several retailers that have you covered, from souvenirs to jewelry.

Discover the Benefits of Renting from Two Pines

The living space of a Big Sky rental to stay at on a Montana spring break vacation.

Choosing Two Pines as your vacation rental provider means you’re getting more than a phenomenal palace to call home. For anyone planning their Montana spring break getaway with us, we highly recommend checking out Two Pines Perks. See if you can save on any of your top adventures with these special discounts offered to our guests.

To learn more about these offerings, call 406-995-2299. Our local staff can also provide more recommendations on this to do during your stay with us. When you’re ready to plan your escape, take your time browsing our inventory to see which Big Sky vacation rental fits your group best. Before reserving your top choice, take a look at our special offers for ways to save.

What Wildlife Can You See in Big Sky, Montana

Big Sky and the surrounding area are known for breathtaking views. Whether exploring a winter wonderland or a trail inside Yellowstone National Park, there are countless ways to discover Mother Nature’s beauty. One of the best things you can do on any outdoor adventure is keep your eyes open for animals that call this area home. To help you have a better idea of what you might spot, the team at Two Pines Properties has put together a list of wildlife in Montana you may stumble upon. 

A Guide to 5 Animals You Can See in Yellowstone and Beyond

One of the best places to go wildlife viewing near your Big Sky rental is Yellowstone National Park. For anyone staying with us during the spring, you might just be able to catch a glimpse of babies! If you are out exploring, remember these are wild animals. While they may look cute and cuddly, you should not approach them. Read up on wildlife viewing tips to ensure your excursion is both fun and safe.

  • Bighorn sheep can be seen in several places throughout Yellowstone. During the summer, they frequent the slopes of Mount Washburn. Keep your eyes open as you drive into Big Sky, as you may see them along the roadways. 
  • Herds of elk call the mountain meadows around Big Sky home. You can often hear the call of the bull elk. The best way to spot these creatures is by driving to the boundary of Yellowstone around dawn or dusk.
  • There are less than 200 moose in Yellowstone, which means spotting one is a special moment. Due to their coloring, it can be hard to spot these animals as they munch around the bushes or riverbeds on the outskirts of town.
  • When you think of Montana wildlife, one of the first things to come to mind is probably the North American bison. Yellowstone is the only place in the country that has had bison since prehistoric times. Over 5,000 bison were counted in the summer of 2022.
  • Black bears are commonly seen throughout the park but most often in the Mammoth and Tower areas. As these animals can climb trees, be sure to turn your eyes toward the treeline.

Embrace the Outdoors on a Big Sky Vacation

A luxury Big Sky vacation rental in Montana you can see wildlife from.

You don’t have to set off on day-long adventures to discover wildlife in Montana. You might just be able to see something off in the distance from the comfort of your Two Pines rental. With properties located all over Big Sky, we have vacation rentals surrounded by stunning wilderness. Sit out on your deck or balcony and let the sound of nature be the soundtrack of your vacation. Call 406-995-2299 to learn more about our luxurious rentals or ways to save on your next visit!

Treat Yourself to Retail Therapy Shopping in Big Sky, Montana

When you think of Montana, you probably think of world-class outdoor adventures. While this is certainly true, there is so much more to discover in Big Sky Country, including incredible local businesses. On your next vacation with Two Pines Properties, spend some time shopping at the diverse stores in Big Sky, Montana. You never know what goodies you might stumble upon!

Where to Shop in Big Sky

The stores in Big Sky have it all, from incredible handcraft jewelry to places to pick up last-minute gear. There are two major shopping areas in town, and our team of local experts has put together a list of what you can expect at both of them.

Big Sky Resort

There’s more to Big Sky Resort than phenomenal skiing. The resort is home to numerous other amenities and attractions, including shopping. 

  • Get your Big Sky souvenirs at Lone Peak Logo, the only official logo-wear store in town. Find everything from t-shirts and hoodies to drinkware.
  • Big Sky Sports is an excellent option for those looking for on and off-mountain equipment from top-name brands.
  • Browse the racks at Provisions + Pendleton filled with stunning alpine-inspired apparel, gifts, and accessories.

Big Sky Center

Big Sky Town Center is a hub for entertainment. In addition to being the location for several events, this area is also home to several shops.

  • ART Gallery of Big Sky showcases Ryan Turner’s Fine Art Photography, known for wildlife and dramatic landscapes.
  • If you’re looking for something with some sparkle, head to Ari O Jewelry, a small artisan jewelry company.
  • Discover what contemporary Western style with an urban twist looks like at Rhinestone Cowgirl, which carries top brands like Ariat and BB Dakota.
  • Another great option for art enthusiasts is Gallatin River Gallery. Take in paintings, sculptures, photography, and one-of-a-kind jewelry from local artists.
  • Montana Supply Co is known as a premier mountain lifestyle store. This means they have everything from outdoor gear to things for the home and more.

Discover Incredible Adventures near Your Big Sky Rental

A Big Sky, Montana, rental near top shopping areas.

Whether you’re going shopping or exploring Yellowstone National Park, there is something for everyone in Big Sky, Montana. See for yourself why travelers come back time and time again by booking your getaway with Two Pines today.

Our collection of luxury Big Sky rentals includes homes and condos, both big and small, which means we can host groups of all sizes. In addition to having all the comforts of home, our properties are centrally located in the best neighborhoods, so adventure is right at your fingertips. For help choosing your dream Big Sky vacation rental, call 406-995-2299. Don’t forget to ask about special offers!

A Summer Like No Other | Plan a Big Sky, Montana Escape

Summer is the perfect time to pack your bags and head out on unforgettable adventures, like one to Big Sky, Montana. Whether planning a getaway for two or the whole family, this town is the ideal destination for everyone, and for good reason. With countless activities and attractions, you won’t have any trouble finding things to do near your Two Pines Properties rental. To help you get a jump start on planning, our team has put together a list of some of the best things to do in Big Sky.

What to Do on a Big Sky Vacation

Summer is a popular time for vacationers to visit Big Sky, and it’s not hard to see why. From sunrise to sunset, there is no shortage of thrilling things to do that’ll leave a lasting impression for years to come.

  • No summer getaway to this region of Montana is complete without spending a day or two in Yellowstone National Park. The national park is filled with some of the best things to do on a sunshine-filled day, including hiking, horseback riding, and sightseeing.
  • Take in views of Big Sky while flying down one of two ziplines found at Big Sky Resort. The Nature Zipline takes about an hour to complete, while the Adventure Zipline is closer to three hours.
  • For a thrilling excursion, reserve your spot on a whitewater rafting tour. Geyser White Water Rafting takes you down the Gallatin River and is open from May through September. They offer trips for all skill levels, making them an excellent option for families.
  • One of the most popular events returns every summer when Music in the Mountains makes its annual return. For over a decade, the free outdoor concert series has brought incredible live music to the Center Stage at Town Center Park on Thursdays from June through September.
  • Plan a delicious meal around the ingredients you find at the Big Sky farmers market. Open from June through September, the market takes place on Wednesdays at Town Center. Not only can you find locally-grown produce and freshly-baked goods, but you can also discover local artwork.

Book Your Summer Getaway Today

The porch of a Big Sky rental to relax on during a Montana summer getaway.

With so many things to do and see in Big Sky during your Montana summer getaway, it’s crucial you have a relaxing place to call home. You get that and more when you stay at a rental from Two Pines. While our luxurious Big Sky rentals are centrally located near top adventures, they provide our guests with a tranquil escape to rest up for another day of fun.
Have all the comforts of home, including fully-equipped kitchens and spacious living areas. We also work to bring your homes that have something extra, like hot tubs or outdoor spaces. Call 406-995-2299 to learn more about our properties or special offers.

Best Hikes & More | Activities in Yellowstone National Park

There’s nothing like spending a sunny summer day in the great outdoors. For those planning an upcoming escape to Big Sky, your Two Pines Properties rental is surrounded by countless adventures that’ll have you surrounded by breathtaking scenery. No trip to this Montana town is complete without spending a day in one of the most popular national parks. During your next visit, give yourself plenty of time to explore some of the best hikes and other activities in Yellowstone National Park.

Basic Park Information

Yellowstone National Park became the first national park on March 1, 1872. The 2.2 million-acre park allows visitors to explore a unique ecosystem of geysers, wildlife, and more. To explore this landmark, you will need to pay an entrance fee; part of that fee goes toward improving services and protecting resources. Before heading out, check the most current road conditions to see if there are any closures or detours. 

The Top Yellowstone Park Activities

After enjoying a delicious breakfast in your Big Sky rental, load up the car and head to the park’s west entrance. Be sure to pack a filling lunch using what you purchased from a local grocery store. The last thing you want is to get hungry and have to leave the park for food. During your visit, there is no shortage of things to do and see.

No matter where your adventures lead you, keep your eyes open for the wildlife that call this area home.

Reserve Your Montana Adventure Base Camp

The bedroom of a Big Sky rental to relax in after exploring the best hikes and other activities in Yellowstone National Park.

At Two Pines, we understand how important the right vacation rental is. After a day exploring the best hikes and other activities in Yellowstone National Park, you want to come space to a place that feels like home. While all of our Big Sky rentals are unique, each one has the comforts of home. Browse our inventory online today to find your dream home away from home. For help reserving your rental or more information on ways to save, call 406-995-2299.