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.

Superhost

The exterior of a mountain chalet is displayed, featuring a combination of wood and stone accents. Snow-covered ground surrounds the home, with tall trees nearby. The backdrop showcases majestic mountains under a clear blue sky with wispy clouds.

Chalet in Big Sky

Big Sky Vacation Rentals: MMH 7 Derringer

Escape to Big Sky Country and stay at Moonlight Mountain Home 7 Derringer, a beautifully designed ski in ski out mountain chalet located right on the slopes. Ideal for families or small groups, this spacious multi-level home offers three luxe bedrooms, three full bathrooms, air conditioning, a private hot tub, a one car garage, and a two car driveway.

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.

Superhost

The chalet-style home featuring a pitched roof with snow-covered eaves is situated among snow-dusted trees. Large windows reflect the clear blue sky, while wooden balconies invite outdoor enjoyment. A snow-covered path leads to the front entrance, enhancing the home's winter setting.

Chalet in Big Sky

4 out of 5 average rating, 6 reviews

Big Sky Vacation Rentals: MMH 7 Bull Dogger

Surrounded by towering pines, this breathtaking chalet-style Moonlight Mountain Home is elevated on a secluded end lot bordering Big Sky woodlands. A stylish 4 Bedroom 4.5 Bathroom Big Sky chalet only steps from the slopes with spectacular views from every angle.

Superhost

The inviting living area features a cozy stone fireplace, surrounded by comfortable seating options including a large sofa and an armchair. Large windows provide abundant natural light, framing views of the mountainous surroundings, while a wooden coffee table sits in the center.

Chalet in Big Sky

5 out of 5 average rating, 5 reviews

Big Sky Vacation Rentals: MMH 4 Mountain Home

If comfort and convenience are important to you on vacation, then look no further! This Moonlight Mountain gem is situated in Big Sky and Moonlight Basin's most sought-after location, Cowboy Heaven and you can ski right to/from the back door of the home.

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.

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