Chalet holiday rentals in Madison County

Ski right to your Chalet!

Amazing ski-in/ski out location! Private Bedroom with Queen bed & single bed (separate bedroom with 2 twin beds also available in separate listing). Your own private bathroom, Smart TV, mini fridge. Wifi. Walking distance to restaurants, bars, nightlife. Bring your own streaming service logins. We do NOT provide cable TV. No Cooking in the room. Leave your toasters and hotplates and crockpots at home.

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: 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 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.

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: 12 Claim Jumper

A slice of heaven awaits in this six-bedroom contemporary home nestled at the base of Lone Mountain, in one of Big Sky’s best neighborhoods, Homestead Chalets. This ski-in/ski-out chalet offers easy access to all things Big Sky!

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 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.

Stunning Ski-In/Ski-Out Mountain Chalet

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