Chalet holiday rentals in Madison County

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Popular amenities for Madison County chalet rentals

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
4.5 out of 5 average rating, 4 reviews

Big Sky Vacation Rentals: 12 Claim Jumper

SallyRating, 5 stars23 months ago
This was the cleanest vacation rental we have ever stayed in. The view was gorgeous, the kitchen was well stocked, and the communication was awesome
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
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 stars3 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
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.
Superhost
Chalet in Big Sky
5 out of 5 average rating, 7 reviews

Big Sky Vacation Rentals: MMH 1 Gambler

KristenRating, 5 stars10 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!

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

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 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
4.5 out of 5 average rating, 4 reviews

Big Sky Vacation Rentals: 12 Claim Jumper

SallyRating, 5 stars23 months ago
This was the cleanest vacation rental we have ever stayed in. The view was gorgeous, the kitchen was well stocked, and the communication was awesome
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
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 stars3 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
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

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