Chalet vacation rentals in Madison County

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.

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.

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.

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.

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.

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.

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.

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.

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!

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.

*New Listing* Stunning Ski-In/Ski-Out Mountain Cha

4 Bedroom - 4.5 Bathrooms - Sleeps 12 - Private Hot Tub - Mountain Village Location - (Property Code: 23 Black Eagle)

Ski-In/Ski-Out Big Sky Home with Incredible Views

CODE 10 Silver Star - 3 Bedrooms with Loft - 4.5 Bathrooms - Sleeps 11 - Private Hot Tub - Moonlight Basin Location