Chalet holiday rentals in Madison County

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Popular amenities for chalet rentals in Madison County

Family-friendly chalet rentals

Guest favourite
Chalet in Dillon
4.99 out of 5 average rating, 81 reviews

Expedition Lodge

LyndaRating, 5 stars5 months ago
The Expedition Lodge was Beautiful and exceeded our expectations! The living room was so cozy and comfortable and the fireplace was perfect. The kitchen was extremely well-equipped with everything we needed for our Christmas dinner. Bedrooms were all very comfortable and everything was so clean and well supplied and organized. We absolutely loved staying there. We were so impressed with everything, even down to the beautifully decorated Christmas tree. Excellent communication from the owner...Thank you!
Superhost
Chalet in Big Sky
4.88 out of 5 average rating, 8 reviews

Big Sky Vacation Rentals: MMH 4 Shadow Ridge

TimRating, 5 stars26 months ago
The house was fantastic. Spacious, clean, fabulous views, great location. The deck though was covered in ice when we arrived, the balcony was snowed in, and the driveway had a lot of compacted snow that caused one of our cars to get deeply stuck. Despite those snafus we really enjoyed our stay. Kids loved the upstairs loft and hot tub!
Superhost
Chalet in Big Sky
4.86 out of 5 average rating, 29 reviews

Big Sky Vacation Rentals: MMH 5 Derringer

HeatherRating, 5 stars11 months ago
Absolutely beautiful place to stay!! The home was spectacular and the views were amazing
Superhost
Chalet in Big Sky
5 out of 5 average rating, 3 reviews

Big Sky Vacation Rentals: MMH 4 Indian Summer

LeslieRating, 5 stars20 months ago
We had a fabulous stay! The views were breathtaking and the home was just as described. There were some dirty towels left in one bathroom but we didn’t need to use that area so no big deal. I’m sure it was an oversight of the cleaning crew. Highly recommend and will stay again if we travel back to big sky!
Top guest favourite
Chalet in Big Sky
4.81 out of 5 average rating, 27 reviews

Big Sky Vacation Rentals: AM 5 Silver Star

RussellRating, 5 stars2 months ago
Excellent place for skiers to stay. Garage is set up perfectly with boot warmers, bench, treated floors, and ski storage. The location is great for ski in and ski out. It’s a slight walk uphill to the trail, but not too bad. When there’s snow on the road, you can literally ski from the trail into the garage. The view from the living room and master bedroom of the mountains is magnificent.
Superhost
Chalet in Big Sky

Big Sky Vacation Rentals: Homestead 16 Claim

PhillipRating, 5 stars40 months ago
16 Claim Jumper was an incredible stay! The ski in/out location is so convenient and the views of Lone Mtn and the Gallatins are wonderful. Plenty of firewood for the real fireplace and a hot tub right on the back porch with views of the ski run were big hits as well. Couple that with the modern, stylish, quality, comfortable accommodations which made the place truly exceptional.
Superhost
Chalet in Big Sky
4.78 out of 5 average rating, 9 reviews

Big Sky Vacation Rentals: MMH 6 Harvest Moon

shannon Rating, 5 stars7 months ago
This mountain chalet was well worth it , and was beautiful We highly recommend it to future guests
Superhost
Chalet in Big Sky
4.8 out of 5 average rating, 10 reviews

Big Sky Vacation Rentals: MMH 4 Harvest Moon

AshleyRating, 5 stars28 months ago
We had a great stay for a long weekend! The skiing was great and easy to access from the property. It’s a very short walk to and from the house for “ski in- ski out” access. The management company gave us wonderful local recommendations and were very responsive. The only negative was that you are no longer able to utilize a guest pass at Moonlight Basin. This used to be an option but changed in April of 2022. Also- I would recommend renting a car or booking transportation in advance as it was difficult to get rides to and from the town. Overall, we had a wonderful experience.

Luxury chalet rentals

Superhost
Chalet in Gallatin Gateway
4.9 out of 5 average rating, 29 reviews

Big Sky Paradise - Arrowhead

JeremyRating, 5 stars3 months ago
Spacious, homey, perfect location, very well-appointed kitchen (pans, dishes, pantry), comfortable furniture/bedding, views are amazing. Wood burning fireplace is perfect, including kindling and seasoned wood. The remodeled master bath with steam shower is wonderful. You’ll want for nothing in this condo. The walk from the garage/parking is steep, so not for the faint of heart (site manager, johnny on the spot, was very helpful hauling our gear up the hill with a four-wheeler and wagon).
Superhost
Chalet in Big Sky
4.88 out of 5 average rating, 8 reviews

Big Sky Vacation Rentals: MMH 4 Shadow Ridge

TimRating, 5 stars26 months ago
The house was fantastic. Spacious, clean, fabulous views, great location. The deck though was covered in ice when we arrived, the balcony was snowed in, and the driveway had a lot of compacted snow that caused one of our cars to get deeply stuck. Despite those snafus we really enjoyed our stay. Kids loved the upstairs loft and hot tub!
Guest favourite
Chalet in Big Sky
4.91 out of 5 average rating, 11 reviews

Spacious Ski-In/Ski-Out Retreat

KellyRating, 5 stars11 months ago
We had an amazing vacation. It was easy to get to bike trails.
Superhost
Chalet in Big Sky
4.86 out of 5 average rating, 29 reviews

Big Sky Vacation Rentals: MMH 5 Derringer

HeatherRating, 5 stars11 months ago
Absolutely beautiful place to stay!! The home was spectacular and the views were amazing
Superhost
Chalet in Big Sky
5 out of 5 average rating, 3 reviews

Big Sky Vacation Rentals: MMH 4 Indian Summer

LeslieRating, 5 stars20 months ago
We had a fabulous stay! The views were breathtaking and the home was just as described. There were some dirty towels left in one bathroom but we didn’t need to use that area so no big deal. I’m sure it was an oversight of the cleaning crew. Highly recommend and will stay again if we travel back to big sky!
Top guest favourite
Chalet in Big Sky
4.81 out of 5 average rating, 27 reviews

Big Sky Vacation Rentals: AM 5 Silver Star

RussellRating, 5 stars2 months ago
Excellent place for skiers to stay. Garage is set up perfectly with boot warmers, bench, treated floors, and ski storage. The location is great for ski in and ski out. It’s a slight walk uphill to the trail, but not too bad. When there’s snow on the road, you can literally ski from the trail into the garage. The view from the living room and master bedroom of the mountains is magnificent.
Superhost
Chalet in Big Sky
5 out of 5 average rating, 3 reviews

Big Sky Vacation Rentals: Coyote Bluff

JeffRating, 5 stars9 months ago
By far the most well managed Airbnb I’ve ever been at. Communicated perfectly, with daily check ins to make sure everything was perfect. View was spectacular, location was beautiful, plenty of bedrooms and bathrooms. Everything was very clean. Would highly recommend as one of the best airbnbs I’ve ever stayed at A+++
Superhost
Chalet in Big Sky

Big Sky Vacation Rentals: Homestead 16 Claim

PhillipRating, 5 stars40 months ago
16 Claim Jumper was an incredible stay! The ski in/out location is so convenient and the views of Lone Mtn and the Gallatins are wonderful. Plenty of firewood for the real fireplace and a hot tub right on the back porch with views of the ski run were big hits as well. Couple that with the modern, stylish, quality, comfortable accommodations which made the place truly exceptional.

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