Chalet vacation rentals in Madison County

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.

4.83 out of 5 average rating, 6 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

5 out of 5 average rating, 3 reviews

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.

5 out of 5 average rating, 5 reviews

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.

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.

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.

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.

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 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.

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.

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.

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.

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.

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.

4.82 out of 5 average rating, 11 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.

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.

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!