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The holiday season is a magical time in Big Sky, Montana, where snow-covered landscapes and a vibrant mountain community come together to create unforgettable experiences. Whether you’re dreaming of a cozy cabin retreat or looking to fill your days with family-friendly holiday activities, Big Sky has everything you need for the perfect holiday escape.

 

Cozy Cabins for the Holidays

The Wildwood Lodge

Imagine waking up in a luxurious mountain cabin surrounded by pristine snow, with the scent of pine trees in the air. Our holiday vacation rentals in Big Sky offer the ultimate combination of comfort, charm, and convenience. Whether you’re gathering with family or friends, these cabins are designed for memorable moments, featuring:


Cozy Cabins for the Holidays in Big Sky

Unwind in a Hot Tub Under the Stars

Hot Tub in Winter Looking into Forest

After a day of holiday activities or carving through fresh powder, there’s no better way to relax than in a private hot tub. Many of our holiday rentals in Big Sky come with outdoor hot tubs, allowing you to soak your cares away while surrounded by stunning natural beauty. Picture yourself beneath a canopy of stars, with the crisp mountain air on your skin and the soothing warmth of the water melting your stress away. Whether sipping hot cocoa with the kids or sharing a toast with friends, a hot tub is the ultimate holiday indulgence.

Vacation Rentals With Hot Tubs

Family-Friendly Activities for the Holidays in Big Sky

Big Sky’s holiday season is brimming with festive events and activities designed to create lasting memories. Here’s what you can look forward to this year:

Signature Big Sky Holiday Events

Holiday Christmas Tree Lighting

Big Sky Christmas Delights

Santa and Kid

Other Family Fun

Two Reindeer in Winter

Ring in the New Year in Big Sky Style

Big Sky also knows how to throw an unforgettable New Year’s Eve celebration! Here are some highlights:

Big Sky Fireworks

Plan Your Big Sky Family Ski Trip

White Wolf in Winter Lone Peak in Background

With its luxurious holiday vacation rentals, festive events, and family-friendly activities, Big Sky is the perfect destination for a memorable family ski trip this holiday season. Don’t wait—secure your cozy cabin and start planning your magical getaway today!


Cozy Cabins for the Holidays in Big Sky

Dice Spelling Staycation on Table

For Bozeman locals, sometimes the perfect vacation is just a short drive away. With its breathtaking landscapes, luxurious accommodations, and a true sense of Montana’s rugged yet welcoming charm, Big Sky is the ultimate nearby destination for a refreshing getaway. Whether you’re craving a quiet weekend retreat or an adventure-filled staycation, Big Sky offers an ideal blend of peaceful serenity and vibrant outdoor activities, making it one of the best staycations near Bozeman. Big Sky redefines what it means to “get away” without venturing far from home.

Quick Drive, Big Change: Why Big Sky is the Ultimate Staycation Destination

Two Girls in Car Driving

Just an hour’s scenic drive from Bozeman, Big Sky is an ideal staycation spot, giving you a refreshing change of pace without the time and hassle of a long trip. Imagine winding through picturesque mountain roads, passing by flowing rivers and dense pine forests as you leave city life behind. Within an hour, the urban rush melts away, replaced by the stillness and grandeur of the Gallatin and Madison mountain ranges. Here, Bozeman locals can fully immerse themselves in nature, reconnect with themselves or loved ones, and enjoy the slower rhythm of mountain life.

For many, Big Sky is not just a place to unwind but a chance to enjoy the Montana dream—a staycation destination where luxury and nature blend effortlessly. The short drive offers an ideal escape that feels worlds away from city stress, and for Bozeman locals who crave quality experiences and memorable adventures, Big Sky is an unbeatable choice. It’s no wonder why so many residents consider Big Sky the ultimate weekend or holiday retreat, one that balances adventure, relaxation, and the essence of Montana. Whether you’re seeking quiet moments under the stars or an adrenaline-packed itinerary in the great outdoors, Big Sky has something to offer every type of staycationer.

Luxury Vacation Rentals Perfect For Staycation

Wilson Peak Properties Vacation Rental in Winter form Above

A staycation in Big Sky offers Bozeman locals a taste of pure luxury right in the heart of Montana. Choosing to stay in one of Wilson Peak Properties’ beautiful vacation rentals is a great way to enjoy the beauty of the area without sacrificing comfort. Each home is thoughtfully curated to provide a warm, inviting environment where guests can feel instantly at home—whether it’s by the stone fireplace with a warm beverage in hand or around a large dining table for a shared family meal.

With gourmet kitchens, plush bedding, and elegant furnishings, Wilson Peak Properties’ homes and cabins elevate the staycation experience to new heights. Enjoy an ideal atmosphere for unwinding, with all the amenities you need for a hassle-free stay, including Wi-Fi, entertainment systems, and, in some cases, private hot tubs, gyms, and game rooms. For Bozeman locals looking for the perfect balance of comfort and wilderness, these luxury homes and cabins make Big Sky one of the best staycation ideas nearby

Browse Big Sky Staycation Vacation Rentals

Private Hot Tubs: Relax Under the Montana Sky

Little Wolf Cabin Hot Tub

Few things capture the essence of a mountain getaway like a soak in a private hot tub under the open sky. Big Sky staycations offer a rare opportunity to enjoy this luxury with stunning views of Montana’s iconic landscape. After a day of skiing, hiking, or exploring the region, you can slip into a private hot tub and let the warmth soothe your muscles while you reflect on the breathtaking scenery.

For Bozeman locals, this unique relaxation experience is a major reason Big Sky staycations have become so popular. The sense of peace and tranquility that comes from such moments is unparalleled, offering a true escape from the fast pace of city life. It’s the perfect way to unwind, rejuvenate, and create lasting memories in one of Montana’s most beautiful settings.

Browse Big Sky Staycation Vacation Rentals With Hot Tubs

Year-Round Outdoor Adventures at Your Doorstep

Person Mountain Biking in Big Sky Montana

Big Sky’s unique location offers endless outdoor adventure options, making it a top choice for Montana staycations. In the winter, Big Sky Resort boasts some of the best skiing and snowboarding in the United States, with varied terrain that caters to everyone from beginners to expert skiers. Cross-country skiing, snowshoeing, and snowmobiling are also popular winter activities that allow guests to experience the pristine beauty of Montana in winter.

When the snow melts, Big Sky transforms into a summer paradise for hikers, mountain bikers, and anglers. With miles of trails, fishing spots along the Gallatin River, and adventure parks nearby, Big Sky offers boundless opportunities to explore and connect with nature. For those who prefer a more relaxed approach, there are plenty of picnic spots, scenic viewpoints, and guided tours to enrich your Montana staycation experience. With something for every type of traveler, Big Sky provides an exciting escape that’s close to home for the Montana locals in nearby areas.

More on Seasonal Festivals & Events

Reconnect with Nature, Family, and Friends

People in Backyard Enjoying Staycation

A staycation in Big Sky isn’t just about getting away; it’s about coming together. Wilson Peak Properties offers spacious accommodations perfect for reconnecting with family, friends, or even just yourself. With space for group gatherings, these cabins create an ideal setting for family reunions, romantic retreats, or friends’ weekends, allowing everyone to enjoy the best Big Sky has to offer.

Browse Big Sky Group Vacation Rentals

 

A Refreshing Weekend Getaway Close to Home

Friends Drinking Wine

The proximity of Big Sky to Bozeman means you can leave on a Friday afternoon and be settling into your cabin by dinner, enjoying a full weekend of relaxation and recreation before the quick drive back. This convenient access to such a high-end destination allows locals to plan last-minute getaways without extensive travel planning, making it one of the top Montana staycations for busy professionals, families, and adventure-seekers alike.

During certain seasons, Wilson Peak Properties offers reduced minimum night stays for local guests wishing to have a quick “Getaway” vacation. Typically listed on our DEAL PAGE check for minimum night stays as short as 2-nights.

Discover Your Perfect Big Sky Staycation with
Wilson Peak Properties

For Bozeman locals looking for the best staycations near home, Big Sky is the answer.

Find Your Big Sky Staycation Rental

Check Deals for Reduced Minimum Nights

Car Driving near Big Sky Montana during Fall

Autumn transforms Big Sky, Montana into a breathtaking tapestry of vibrant colors, crisp air, and serene landscapes. As the summer rush fades and before the winter ski season kicks in, Big Sky emerges as a peaceful paradise for fall enthusiasts and locals that just want to slip away. This quiet period offers the perfect opportunity to explore the area’s natural beauty through Montana fall hikes, scenic drives, and outdoor adventures. Whether you are a nature lover, adventure seeker, or simply looking to unwind, Montana in the fall offers an unforgettable experience.

The Beauty of Fall in Big Sky

Montana is known for its wide, open spaces, and in the autumn months, these spaces are draped in stunning fall foliage. The changing leaves create a colorful contrast against Montana’s rugged mountains and vast meadows. If you’re a lover of nature, you’ll be captivated by the Montana fall colors, as the landscape shifts from shades of green to fiery reds, yellows, and oranges. The crisp fall air, paired with the golden hues of the leaves, makes this season the perfect time to visit Big Sky.

Fall Hikes: Explore Montana’s Natural Beauty

Woman Relaxing on Fall Hike at Top of MountainOne of the best ways to experience autumn in Montana is through hiking. The trails are quieter than in the summer, and the cool weather makes for comfortable trekking. Some top trails near Big Sky include:

More Hiking Trails

Scenic Drives: A Picture-Perfect Road Trip

If hiking isn’t your style, a scenic drive through Big Sky and the surround mountains is equally breathtaking. One of the best routes is the drive along Highway 191, which takes you through the Gallatin Canyon. With the towering Gallatin River on one side and golden aspens on the other, this drive offers an unforgettable visual feast. Another great option is the Big Sky Scenic Byway, which showcases miles of Montana fall colors that highlight the beauty of the changing season.

Adventure and Tranquility Before Ski Season

Caught Trout in RiverBig Sky offers much more than just scenic views. The autumn months provide an ideal time for outdoor adventures and tranquil getaways. With fewer tourists around, it’s easy to find solitude in nature while enjoying your favorite activities. Some of the top seasonal activities include:

Halloween Festival + Fall Events

Autumn in Big Sky also brings a handful of seasonal events and festivals that celebrate the season. Local weekly events for football, trivia, and dancing are popular plus a few annual festivities like the Skull and Roses Ball and the Haunted Peaks Halloween Festival, which is typically 3 days of Halloween celebration at the Big Sky Town Center. These events are perfect for catching great music, sharing family time, and simply enjoying the warm, community spirit that thrives during our Falls in Big Sky.

More on Seasonal Festivals & Events

Cozy Accommodations for Your Perfect Fall Escape

Back of Vacation Rental BobtailAfter a day of exploring Montana’s beautiful autumn landscapes, nothing beats returning to a cozy accommodations. Warm up by the fireplace with a cup of hot cocoa, or relax in a hot tub under the stars as you soak in the peacefulness of Big Sky’s fall season. Consider luxury mountain lodges with stunning views or, if you prefer, a quaint cabin tucked away in the forest, either way the perfect retreat is waiting. With its breathtaking scenery and endless opportunities for outdoor adventures, Big Sky is the ultimate destination for a Montana autumn getaway. Book your stay with Wilson Peak Properties to experience the beauty of fall in the mountains.

Browse Big Sky Fall Vacation Rentals

Madison 8 Chairlift Rendering

Big Sky Ski Resort is already one of North America’s top ski destinations, but it’s set to become even more extraordinary. In 2025, the resort will unveil the Madison 8 Chairlift, the largest and most advanced chairlift in the world, solidifying Big Sky’s position as a leader in ski resort innovation.

What is the Madison 8 Chairlift?

The Madison 8 is part of Big Sky’s ongoing commitment to creating an unmatched ski experience. This state-of-the-art, high-speed chairlift is designed to cut down lift wait times significantly, offering skiers and snowboarders faster access to the expansive terrain.

Here’s what makes the Madison 8 special:

How the Madison 8 Enhances the Big Sky Experience

Big Sky Ski Resort is known for its incredible range of terrain, and with the new Madison 8 Chairlift, access to that terrain will be easier and faster than ever. Whether you’re an advanced skier looking for challenging runs or a beginner hoping to enjoy the scenic slopes, the Madison 8 will improve your time on the mountain.

This lift will also reduce bottlenecks and congestion, making your skiing experience smoother. Plus, the additional comfort features mean that even on cold days, you’ll enjoy a warm, sheltered ride to the top.

Planning Your Trip to Big Sky in 2025Wilson Peak Properties Vacation Rental in Winter form Above

If you’re thinking about booking a trip to Big Sky in 2025, the Madison 8 Chairlift should definitely be on your radar. The upcoming season promises shorter lift lines, more comfortable rides, and even more time to explore Big Sky’s vast terrain. With the Madison 8 Chairlift opening, Big Sky Ski Resort is continuing its legacy of innovation and world-class skiing. Be sure to plan your trip to experience this cutting-edge lift firsthand and enjoy a faster, more comfortable, and thrilling ride to the top.

For those looking to stay near the slopes, Wilson Peak Properties offers luxury lodging options that provide easy access to the resort’s best features. Whether you’re planning a winter adventure or considering a longer stay, our properties are the perfect base for enjoying all that Big Sky has to offer.

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