Chalet vacation rentals in Madison County

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Top-rated chalet rentals in Madison County

Guests agree: these chalets are highly rated for location, cleanliness, and more.

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Superhost

The exterior of the chalet is presented with a snow-covered surface and a spacious wooden deck. The structure features multiple gabled roofs, contrasting materials of wood and stone, and large windows that invite natural light. The surrounding snow-capped landscape enhances the alpine retreat's charm.

Chalet in Big Sky

4.8 out of 5 average rating, 5 reviews

Big Sky Vacation Rentals: Homestead 5 Claim Jumper

Homestead Chalet 5 is a luxury ski in / ski out mountain retreat situated within Big Sky Resort. This stunning chalet features tons of desirable amenities including thoughtful interior design, modern finishes, a private hot tub, dedicated boot dryers & ski storage, a Peloton bike & shuffleboard table, and a variety of sleeping options making this home the perfect choice for larger groups or families traveling together. Located just minutes from Mountain Village and within an hour drive

Superhost

Chalet in Big Sky

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.

Superhost

The chalet features a modern A-frame design with a distinctive brown exterior. Large windows provide ample natural light, and a covered entrance is visible from the front. Surrounding greenery adds to the serene mountain environment.

Chalet in Gallatin Gateway

4.9 out of 5 average rating, 31 reviews

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.

Superhost

Chalet in Big Sky

New to Market! 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.

Top guest favorite

A rustic lodge is showcased at dusk, with warm light glowing from large windows. The building is framed by lush green grass and trees, adding to its inviting presence. The gentle slope of the lawn leads up to the welcoming front porch.

Chalet in Dillon

4.99 out of 5 average rating, 84 reviews

Expedition Lodge

My place is close to great views, restaurants and dining, and family-friendly activities. You’ll love my place because of the location, the ambiance, and the outdoors space. My place is good for couples, business travelers, families (with kids), and big groups. The outdoor rock fireplace is a customer favorite, and the sunsets are photo worthy.

Superhost

A spacious living area features a prominent stone fireplace, framed by large windows that offer panoramic views of the surrounding mountains. Various seating options, including leather sofas and a cozy chair, are arranged around a light-colored coffee table. Natural light enhances the warm wood tones and neutral décor.

Chalet in Big Sky

4.88 out of 5 average rating, 34 reviews

Big Sky Vacation Rentals: MMH 5 Derringer

Experience mountain living at its finest in this Big Sky home situated atop Cowboy Heaven on the Moonlight side of Lone Mountain. Big Sky Resort ski access doesn’t get better than this with America's Biggest Skiing right off your back deck! This home was recently renovated and has new furniture, paint and art, throughout.

The exterior of the two-story chalet features a spacious patio with a dining table and chairs. A hot tub is positioned nearby, surrounded by a verdant lawn. Large windows in the upper floor allow for ample natural light, and the surrounding trees contribute to a serene setting.

Chalet in Big Sky

4.75 out of 5 average rating, 36 reviews

2 Bed ski out Apt in Private Home

Luxurious ski in - out rental apartment in private ski lodge in Big Sky, Montana. Full home comforts. Groomed ski trails to the resort lifts. Located on a warm southern facing slope of the Big Sky ski area, with panoramic views.

Superhost

A stylish alpine home is nestled among snow-covered trees, showcasing a spacious deck with stunning views of distant mountains. The exterior features a blend of stone and wood accents, enhancing the natural surroundings while the snow-covered path provides direct access to ski activities.

Chalet in Big Sky

4.86 out of 5 average rating, 7 reviews

Big Sky Vacation Rentals: MMH 44 Cowboy Heaven

Set on a sunny perch high in Cowboy Heaven overlooking the Spanish Peaks, this tasteful alpine home tucked in the woods offers a top Big Sky ski-in/ski-out location with direct access to the slopes from your back door.

Guest favorite

The living area features a large stone fireplace as the focal point, surrounded by comfortable leather seating. Notable is the row of tall windows that showcase expansive mountain views, allowing natural light to fill the space. A rustic coffee table completes the cozy atmosphere.

Chalet in Big Sky

4.82 out of 5 average rating, 28 reviews

Big Sky Vacation Rentals: AM 5 Silver Star

This luxurious Alpine Meadows ski chalet is perched high on the slopes of Moonlight Mountain, secluded in a quiet cul de sac in the pines, with direct ski-in/ski-out to the uncrowded slopes of Big Sky Resort.

Superhost

A stylish alpine retreat is surrounded by snow-covered slopes and tall pine trees. The exterior features multiple levels with large balconies that overlook the winter landscape, with a path leading toward the entrance. The bright blue sky adds to the serene mountain atmosphere.

Chalet in Big Sky

4.8 out of 5 average rating, 10 reviews

Big Sky Vacation Rentals: MMH 6 Harvest Moon

Moonlight Mountain Homes offer some of Big Sky’s finest lodgings and from its sunny perch up in Cowboy Heaven, this ski-in/ski-out stylish alpine retreat does not disappoint.

Guest favorite

The exterior of a spacious alpine home features a combination of wooden and stone elements. A large deck extends from the upper level, offering views of the snow-dusted landscape and surrounding mountains under a clear blue sky.

Chalet in Big Sky

5 out of 5 average rating, 9 reviews

Big Sky Vacation Rentals: MMH 1 Gambler

This high altitude alpine hideaway in Cowboy Heaven overlooks the Spanish Peaks and boasts both breathtaking mountain views and outstanding ski access from your door!

Superhost

A spacious living room features a large stone fireplace, surrounded by a cozy sectional sofa adorned with decorative pillows. Natural light floods the space through large windows, offering views of surrounding trees. A wooden coffee table sits atop a patterned area rug, enhancing the warm and inviting atmosphere.

Chalet in Big Sky

4.82 out of 5 average rating, 11 reviews

Big Sky Vacation Rentals: MMH 4 Harvest Moon

Moonlight Mountain Homes are situated on the slopes in Cowboy Heaven with easy access to the “Biggest Skiing in America” and endless alpine adventures.