Chalet vacation 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

New! Ski-in/ski-out condo w hot tub & grill

Welcome to The Snowline Chalet, a true ski-in/ski-out townhouse nestled in Big Sky’s Saddle Ridge community. This three-bedroom, two-and-a-half-bath home spans three levels, each offering sweeping valley views, multiple balconies, a private hot tub, and a grill. With true ski-in/ski-out access, guests can hit the slopes effortlessly via the nearby Iron Horse Lift—the preferred choice for quick access to Big Sky’s vast terrain. The Pony Express Lift also provides additional access.

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.

Ski-in/ski-out home in Moonlight Basin w/hot tub

Ski-in/ski-out from this 2 bedroom/2.5 bathroom Saddle Ridge townhome. As you walk in, the main level opens to the kitchen, gas fireplace, dining area, and breakfast bar. Walk out on our deck to take in the views while cooking on our gas grill. Upstairs you will find the master suite with a king bed and private bath. As you make your way downstairs from the main entryway you will find bedroom suite number 2. This room contains a queen bed and a twin/twin bunk bed.

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.

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.

Ski-in/out | Dog Friendly | Hot Tub | Moonlight

Ski-in/ski-out in Moonlight Basin, steps from the Pony Express lift. Spanish Peaks views, a private hot tub, and genuine mountain quiet year-round. Hike and bike from the property in summer, with Yellowstone just over an hour away. Three bedrooms, a full kitchen, NFL Sunday Ticket, and one dog welcome.

Homestead Chalet 4 | Ski-in/Out 6BR w/ Hot Tub

It’s not easy to find a six-bedroom home in Big Sky and definitely not one as simply stunning as Chalet 4. This contemporary mountain home is perched on Lone Mountain in Big Sky Resort's newest and most sought-after development, with effortless access to the slopes. The best in Big Sky Lodging.

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.

Silver Star Alpine Lodge | Ski-In/Out Chalet |

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.