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

A spacious chalet-style home is set against a backdrop of snow-covered trees. Large windows provide views of the outdoors, while the wrap-around deck features wooden railings. The driveway is partially visible, surrounded by snow and leading to the garage.

Chalet in Big Sky

5 out of 5 average rating, 4 reviews

Big Sky Vacation Rentals: MMH 4 Indian Summer

Located in the Cowboy Heaven neighborhood on the Moonlight side of Lone Mountain, this stunning ski in ski out chalet offers the ultimate Big Sky escape in every season. Only minutes from the Mountain Village and a scenic 45 minute drive from Yellowstone National Park, this chalet is ideally located for summer adventures or winter escapes. Spanning 2,600 square feet, this luxury mountain sanctuary comfortably sleeps eight in beds (ten guests max, including sofa sleeper) and is the ideal choice

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

4.91 out of 5 average rating, 32 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.

Guest favorite

A stunning mountain chalet is nestled among snow-covered pines, showcasing a blend of rustic wood and modern architecture. The two-story home features expansive windows and multiple balconies, inviting natural light and views of the surrounding landscape. A driveway leads up to the entrance, enhancing accessibility.

Chalet in Big Sky

5 out of 5 average rating, 6 reviews

Big Sky Vacation Rentals: Coyote Bluff

This 4 bedroom 4.5 bathroom ski-in/ski-out Big Sky mountain chalet is perfectly perched on the slopes of Cowboy Heaven with unobstructed views of the Spanish Peaks Mountain Range, top-of-the-line indoor and outdoor amenities and elegantly curated interiors for a luxury vacation in Big Sky, MT.

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

Chalet in Big Sky

4.57 out of 5 average rating, 7 reviews

Big Sky Vacation Rentals: 12 Claim Jumper

A slice of heaven awaits in this six-bedroom contemporary home nestled at the base of Lone Mountain, in one of Big Sky’s best neighborhoods, Homestead Chalets. This ski-in/ski-out chalet offers easy access to all things Big Sky!

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.