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, 5 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, 33 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.

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.

Superhost

A modern mountain chalet presents an inviting facade with a combination of wood and stone materials. Expansive windows reflect the surrounding snow-covered landscape, while a single-car garage is visible on the right side. The two-story structure features a welcoming entrance under a sloped roof.

Chalet in Big Sky

5 out of 5 average rating, 3 reviews

Big Sky Vacation Rentals: Homestead 16 Claim

Chalet 16 is the epitome of modern mountain living! Offering the best ski access of any of the Homestead Chalets perfectly situated directly on the ski trail just above Powder Ridge. This exclusive vacation rental is the ultimate ski-in/ski-out Big Sky option for large groups looking for comfort, convenience.

Superhost

The chalet-style home is situated amid snow-covered pines, showcasing large windows and a prominent stone chimney. A spacious wrap-around deck is visible, offering views of the surrounding mountain landscape. The warm wood tones of the exterior contrast with the snowy surroundings.

Chalet in Big Sky

4.88 out of 5 average rating, 8 reviews

Big Sky Vacation Rentals: MMH 4 Shadow Ridge

From its sunny perch up in Cowboy Heaven, this ski-in/ski-out chalet-style home is a mountain lover’s haven boasting amazing ski slope views and access to the slopes from your driveway! Luxurious alpine living, perfect views, and unmatched ski access, all you need for an awesome Big Sky vacation.

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

4.79 out of 5 average rating, 29 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.

Guest favorite

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

4.83 out of 5 average rating, 12 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