Chalet vacation rentals in Madison County

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Popular amenities for Madison County chalet rentals

Family-friendly chalet rentals

Superhost
Chalet in Big Sky
4.86 out of 5 average rating, 7 reviews

Big Sky Vacation Rentals: MMH 44 Cowboy Heaven

ElizabethRating, 5 stars4 months ago
Amazing ski in ski out location! Wonderful location!
Guest favorite
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
4.86 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, 5 reviews

Big Sky Vacation Rentals: MMH 4 Mountain Home

WilliamRating, 5 stars27 months ago
A beautiful home. Clean. White sheets and towels. Well appointed kitchen with all the necessary tools. We took advantage of the location (ski-in, ski-out) to stop for lunch during the ski day. The hot tub was used daily. Having a heated garage for one vehicle was very convenient. Big Sky was very responsive to our needs. Overall, a great family experience.
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!
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.
Superhost
Chalet in Big Sky
4.5 out of 5 average rating, 6 reviews

Big Sky Vacation Rentals: Homestead 10 Claim

SahalaRating, 5 stars57 months ago
Beautiful location. Stylish, comfortable spaces great for a large family. This is the best vacation rental I've stayed in. Quality appliances and amenities. It's an experience on its own living right in the mountains at 7800 feet. You can hike right out the door, or check out many other recreation locations within a short walk or drive. Would love to also experience winter here! With covid we were worried about sanitization. Not only was the place cleaned well and sprayed down, but they let extra time for the place to be aired out. Also, the management was very quick to respond when we had some safety questions. Very pro.

Luxury chalet rentals

Superhost
Chalet in Big Sky
4.86 out of 5 average rating, 7 reviews

Big Sky Vacation Rentals: MMH 44 Cowboy Heaven

ElizabethRating, 5 stars4 months ago
Amazing ski in ski out location! Wonderful location!
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

Big Sky Vacation Rentals: MMH 7 Derringer

RyanRating, 5 stars5 months ago
The view was better in person than you can imagine. Great place, great skiing and will definitely be back.
Guest favorite
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!
Guest favorite
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
5 out of 5 average rating, 5 reviews

Big Sky Vacation Rentals: MMH 4 Mountain Home

WilliamRating, 5 stars27 months ago
A beautiful home. Clean. White sheets and towels. Well appointed kitchen with all the necessary tools. We took advantage of the location (ski-in, ski-out) to stop for lunch during the ski day. The hot tub was used daily. Having a heated garage for one vehicle was very convenient. Big Sky was very responsive to our needs. Overall, a great family experience.
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!
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 stars9 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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