Chalet holiday rentals in Madison County

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.

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: 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.

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.

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.

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: 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.