Chalet holiday rentals in Madison County

Ski-in/Ski-Out Condo Private Hot Tub Moonlight

This Ski-In Ski-Out, 3 bed 2.5 bath townhome featuring a private hot tub in Big Sky, MT is your perfect winter getaway! This rustic getaway is steps away from the Iron Horse lift at Big Sky resort with unbeatable views of Lone Peak. Inside you are greeted by a cozy atmosphere with a open concept kitchen and living room. The kitchen features stainless steel appliances with everything you need to make a meal for the whole crew. The living room features a gray stone fireplace and easy access to t

Big Sky Vacation Rentals: MMH 4 Indian Summer

Located in the Cowboy Heaven neighborhood on the Moonlight side of Lone Mountain, this stunning ski in ski out chalet offers the ultimate Big Sky escape in every season. Only minutes from the Mountain Village and a scenic 45 minute drive from Yellowstone National Park, this chalet is ideally located for summer adventures or winter escapes. Spanning 2,600 square feet, this luxury mountain sanctuary comfortably sleeps eight in beds (ten guests max, including sofa sleeper) and is the ideal choice

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.

Ski In, Slope Views, Private Hot Tub

Steps from the Iron Horse lift, Timber Wolf Chalet puts you slope-side at the biggest skiing in America. Ski in, drop your gear, and sink into the private hot tub with mountains staring back at you. Four bedrooms, 3.5 baths, and room for 10 spread across three levels. The great room has a gas fireplace and double decks made for morning coffee and après drinks. Kitchen is fully stocked, WiFi is fast, and the slopes are literally outside your door. This one books fast for a reason.

Luxe Mountain Home | Lone Peak Views | Hot Tub

★ Welcome to Big Sky Bliss, a thoughtfully designed mountain retreat for families and group getaways seeking space, comfort, and unforgettable views. ★ Nestled on a scenic slope near Big Sky Resort in the heart of the Gallatin Mountains, this newly remodeled home offers unobstructed Lone Peak views, modern upgrades throughout, and plenty of room for everyone to gather, reconnect, or enjoy a peaceful mountain escape year-round.

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.

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.

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.

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!