Chalet holiday rentals in Big Sky

Modern Mountaintop Retreat

This sunlit home is nestled on the side of the Bridger Mountain range, just 10 minutes from downtown Bozeman and 25 minutes from Bridger Bowl Ski Hill. You will have 60 acres of stunning pine forests to explore or ski. Watch the sunset over the whole valley from the porch or snuggle up by the wood burning fireplace- this home has something for everyone and fast, efficient wifi for remote work. A one of a kind Montana experience that combines rugged natural beauty and thoughtful, modern design.

Ski-In/Ski-Out Luxury Chalet at Big Sky Resort

Welcome to your mountain getaway in Big Sky! This four-bedroom, 3,033 square-foot residence offers the perfect blend of luxury, comfort, and adventure—with direct ski-in/ski-out access to some of the best terrain in North America. The slopeside setting places world-class skiing at your back door, while Mountain Village shops, dining, and après-ski are just a short walk away. To make your trip even easier, our partner Ski Butlers delivers top-of-the-line rental equipment right to your door.

Lonely Mountain Chalet

Experience the ultimate mountain getaway at this luxury mountainside condo, located next to Bridger Bowl Ski Area and directly across from Crosscut Mountain Sports Center! Imagine stepping out the door onto pristine snow or lush trails, surrounded by the breathtaking beauty of the Custer Gallatin National Forest, this chalet is an outdoor enthusiast's dream. From exhilarating downhill and cross-country skiing in winter to world-class mountain biking and hiking in summer, adventure awaits!

Bridger Bowl - Crosscut Hideaway!

Enjoy fresh air and mountain living in this brand new 2 bedroom, 2.5 bathroom, luxuriously furnished home. Located between Bridger Bowl Ski Area and Crosscut Nordic Ski/Bike Area, there are plenty of activities to enjoy right out the front door. Ample hiking, biking and fishing in the summer time as well as downhill, backcountry, and cross country skiing in the winter, to name a few. Enjoy cozy nights around the fireplace while taking in alpine views from every window.

Modern Rustic A-Frame | King Loft w/Bridger Views

Escape to a modern rustic A-frame guesthouse on a shared 5-acre property, tucked away at the end of a quiet road just 10 minutes from downtown Bozeman, 15 minutes from the airport, and 20 minutes from Bridger Bowl. Enjoy a private entrance, soaring ceilings, a full kitchen, a queen bedroom, and a king loft with Bridger Mountain views. Ideal for couples, solo travelers, and business guests. Not suitable for infants or children due to the loft ladder and resident dogs.

Modern Upper Pines Chalet

4 bed/4bath chalet. Plenty of room and privacy for multiple families with baths for every bedroom. Home includes a chef's kitchen, large private hot tub, game room, and a balcony with grill and fire pit. Enjoy spectacular views of the local mountains including Lone Peak. Less than 5 minute drive to Town Center for shopping, dining, and festivals and 10 minutes to the Big Sky resort for world class skiing and biking. Perfect year-round escape for your family.

‼️3BR Big Sky Getaway w/ Hot Tub and Mountain View

》Hit '♡ Save' and relax in our cozy Big Sky chalet—perfect for families or groups, with stunning mountain views and space for 8. ✦ 3 comfy bedrooms + loft with sleeper sofa. ✦ Hot tub with mountain views. ✦ Fully equipped kitchen with everything you need. ✦ Washer/dryer in-unit & all essentials provided. ✦ 6 miles to Big Sky Resort, 50 miles to Yellowstone. ✦ Baby gear, board games & kid-friendly extras. Book your peaceful Montana escape now!

Town Ctr | Mtn View | Hot Tub | Fireplace l Loft

Beautifully designed 3BR/3BA + loft Firelight chalet with attached garage in the heart of Big Sky. Perfect for families, groups or couples, this spacious retreat offers comfort and convenience just steps from Town Center. Enjoy world-class skiing, hiking, golf, fishing, and rafting, with Yellowstone and Bozeman only 45 minutes away. Nestled in a peaceful setting, it’s the ideal home base to relax, explore, and create lasting memories.

Cozy Log Cabin w/ stunning 360 views!

• Secluded but only 8min drive to downtown Bozeman • Stunning 360 views ~> 4+ mountain ranges • Swimming pond on property w/ beach volleyball court! • Bridger Bowl Ski Area (15min drive) • Rocky Creek Nordic Ski Area just down the hill (ski there!) • Rocky Creek for fly fishing (10min walk) • Nearby Yellowstone Park (~1.5hr drive) Can sleep up to 5: Three bedroom w/ open dining & living room areas, sweeping decks (cover & open).

Ski-in/out Moonlight Basin home w/private hot tub

Don't miss the rare, true ski-in/ski-out opportunity to stay only steps from the Iron Horse lift in The Iron Horse Haven Chalet, 2 bedroom Saddle Ridge that sits on the slope.This property literally sits on the slopes! We guarantee that if you stay in this unit, you will never need to carry your skis! Ski to the Iron Horse or Pony Express lift in seconds and take your pick, Big Sky or Moonlight Basin.

Big Sky Paradise - Arrowhead

One of the most amazing ski-in/ski-out locations in Big Sky. Our 4-bedroom, 4 bath, 3 level chalet at the base of Silverknife ski run has everything you need to comfortably accommodate 8 guests. There are no other ski-in/ski-out chalets with 3 ensuite bedrooms (private bathroom/ shower) and wood burning fireplaces in the living room this close to the ski lifts, at this price, with our views.

Vast Ski In/Ski Out Big Sky Chalet

Luxury Ski-in/Ski-out Retreat in Big Sky, Montana <br><br>Experience the ultimate mountain escape at this stunning 6-bedroom, 8-bathroom ski-in/ski-out home, nestled in the heart of Big Sky, Montana. Whether you're here to carve the slopes, unwind by the fire, or explore the breathtaking landscapes, this luxurious retreat is the perfect base for your adventure.