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 stars4 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 stars25 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
4.75 out of 5 average rating, 4 reviews

Big Sky Vacation Rentals: Homestead 5 Claim Jumper

Ny (Mia)Rating, 5 stars36 months ago
Great location. Very spacious house, and accommodated 9 adults without feeling crowded in one house. The hot tub was amazing! We had a friendly red fox visit us and hung around the back patio and porch.
Superhost
Chalet in Big Sky
5 out of 5 average rating, 7 reviews

Big Sky Vacation Rentals: MMH 1 Gambler

KristenRating, 5 stars9 months ago
Absolutely outstanding location with unreal views of the mountains! The house was spacious, clean and perfect for hosting a family vacation! Big Sky Vacation Rentals was very responsive and went above and beyond to make sure we had what we needed. Would recommend this home, location and service team over and over again!
Chalet in Big Sky
4.75 out of 5 average rating, 36 reviews

2 Bed ski out Apt in Private Home

MichaelRating, 5 stars15 months ago
William’s apartment is a wonderful ski in ski out base camp for a trip to big sky. Kitchen has all the basics you need for cooking, and the apartment is clean and cozy. Hot tub has a beautiful view of lone peak. Would highly recommend and would stay again.
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 stars1 month 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.

Luxury chalet rentals

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

Big Sky Paradise - Arrowhead

JeremyRating, 5 stars2 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).
Guest favourite
Chalet in Big Sky
4.84 out of 5 average rating, 49 reviews

Luxurious Black Eagle Chalet

JasmeetRating, 5 stars2 months ago
Great home in Mountain Village. Just a few minute walk from the Swift Current & Ramcharger lifts. Bus down to Big Sky Village also just a few minutes away. Views of Lone Mountain from multiple rooms and the hot tub. Heated garage with boot drying system. Sonos sound system throughout the house. Perfect spot for a group visiting Big Sky Resort!
Superhost
Chalet in Big Sky
4.88 out of 5 average rating, 8 reviews

Big Sky Vacation Rentals: MMH 4 Shadow Ridge

TimRating, 5 stars25 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 stars10 months ago
We had an amazing vacation. It was easy to get to bike trails.
Superhost
Chalet in Big Sky
4.75 out of 5 average rating, 4 reviews

Big Sky Vacation Rentals: Homestead 5 Claim Jumper

Ny (Mia)Rating, 5 stars36 months ago
Great location. Very spacious house, and accommodated 9 adults without feeling crowded in one house. The hot tub was amazing! We had a friendly red fox visit us and hung around the back patio and porch.
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 stars1 month 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 stars8 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
4.86 out of 5 average rating, 7 reviews

Ski In/Ski Out Big Sky Home with Incredible Views

JoanneRating, 5 stars8 months ago
We loved our stay. We had trouble with getting the Wi-Fi going and they sent someone right away to help us. We asked if we could get a few more chairs for the deck and they got them for us. We were able to get an early check-in. The house was great and very well equipped. Hot tub on the deck was awesome. Questions were answered in a timely manner and recommendations for the area were helpful. The house is a ski out for the winter months but we were able to use them for walking in the summer. Loved our stay and would definitely return.

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