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.

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.

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: Homestead 14 Claim

This Big Sky Lodging ski-in/ski-out chalet sets the benchmark for contemporary modern mountain living! Perfectly situated just above Powder Ridge with easy access to the Big Sky lifts, this six bedroom home is an ideal base for larger groups to gather and explore Big Sky Country.

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 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.

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.

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 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.