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Chalet holiday rentals in Jamaica

Find and book unique chalets on Airbnb

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Popular amenities for chalet rentals in Jamaica

Family-friendly chalet rentals

Superhost
Chalet in Peru
4.88 out of 5 average rating, 64 reviews

Getaway in Green Mountains

AndrewRating, 5 stars4 months ago
We stayed here with another couple and their dog two years back and had a wonderful time. I am so grateful that we came back this year with our dog, Chili, and she had the absolute best time! Old Manchester rd is really quiet and is great for off leash walks. Chili loved frequently seeing the other neighbors and their dogs (who were all friendly) on her walks. We’re also runners and so the road is great for running (mostly flat, minimal traffic, frequently plowed, amazing views of Bromley). Jennifer and Dan are both very friendly too. Jennifer did a good job of reaching out to us often making sure we had what we needed. Dan often came by to plow the driveway which was really nice too. Our last day was during a snow storm and they were flexible with checkout which was really helpful. This place really has everything you need and the location is excellent (close to Stratton, Manchester which has a dog park, and downtown Peru which has an outdoor ice skating rink
Guest favourite
Chalet in Mount Holly
4.97 out of 5 average rating, 152 reviews

Charming Summit View Chalet near Okemo and Lakes

LynnRating, 5 stars4 months ago
We enjoyed our stay at the Chalet in Mt Holly. It was our first time not using a Ski In/Ski Out and we were not sure how we would like it. The location was private and the surrounding were so beautiful and peaceful. Libby was very responsive and easy to work with. The home itself was comfortable and clean. We would definitely consider staying here again.
Guest favourite
Chalet in Wilmington
4.95 out of 5 average rating, 98 reviews

Rustic Sunny Vermont Home near Mount Snow

AndreaRating, 5 stars3 months ago
Couldn't say enough great things about both the hosts and the property. Just lovely home - very spacious, and clean and cosy. The area is gorgeous, with a lot to do. Mt. Snow and Hermitage skiing are very close, and Wilmington and the area are charming. Host was very gracious and kind..thank you!
Guest favourite
Chalet in Ludlow
4.82 out of 5 average rating, 76 reviews

Mountain Chalet + HOT TUB

ChristopherRating, 5 stars3 months ago
Great place to stay for okemo mountain!! Very close to local restaurants and the mountain
Superhost
Chalet in Jamaica
4.78 out of 5 average rating, 453 reviews

Chalet 7min to Ski Stratton-WoodStove,Views,DogsOK

JasonRating, 5 stars3 weeks ago
The chalet is secluded, quiet and peaceful. We appreciated its location in the woodland, right near a stream. It was comfortable for our family and we would return again in the future.
Guest favourite
Chalet in Ludlow
4.95 out of 5 average rating, 129 reviews

Okemo Ski Chalet with Hot Tub

WillRating, 5 stars1 month ago
Stop scrolling, you found your next vacation. Bob is a fantastic host with a stunning home. We have stayed with Bob many times and he continues to invest in the property and ensures your stay is nothing short of fantastic. Cannot recommend the ski chalet enough.
Superhost
Chalet in Jamaica
4.86 out of 5 average rating, 94 reviews

Pickleball Pool Golf 7min-Stratton DogsOK Fire Pit

DanielRating, 5 stars3 months ago
Our stay was fantastic. The house was conveniently located relative to Stratton mountain, very comfortable, and the host was fantastic
Top guest favourite
Chalet in Dover
4.97 out of 5 average rating, 113 reviews

Grey Wolf's Den: 5 miles to Mount Snow w/HOT TUB

CaterinaRating, 5 stars3 months ago
Great location! This was a two family trip up to Mt Snow. We had a wide range of ages and 2 dogs. The house had plenty of toys and things for the kids to do - their favorite was the scavenger hunt! The kitchen is one of the best stocked kitchens compared to other Airbnbs we have used. The beds were comfortable - plenty of extra pillows and blankets. The couch and chairs in the living area were also very comfortable. The hot tub was very nice and enjoyable after everyone went skiing.

Luxury chalet rentals

Top guest favourite
Chalet in Wilmington
5 out of 5 average rating, 62 reviews

Beautiful Home on 22 Acres w/Ponds & Central A/C

Christopher WRating, 5 stars1 month ago
Beautiful place. The house, the land. My family of 5 and our dog loved it. The kids loved the ponds and the games room. Vanessa was a great host and helped make it a great experience from start to finish. Cheers!
Top guest favourite
Chalet in Charlemont
4.99 out of 5 average rating, 104 reviews

The Lodge on Warner Hill

AllisonRating, 5 stars3 weeks ago
It was remote compared to the graduation we were attending in the area but we all felt worth the distance. Very comfortable, incredibly clean, well designed house. We had freezing weather so were not able to use the deck or fire pit area. Thank you, Michelle!
Top guest favourite
Chalet in Dover
5 out of 5 average rating, 35 reviews

Charming Mountain Chalet w/ Spa near Mt Snow

Caitlin Rating, 5 stars3 months ago
Lovely stay in a cozy, comfortable house only 15 minutes from Mount Snow. We enjoyed post ski-day nights by the fire, with plenty of comfortable seating and board games galore. The yard was great for our dogs and features like the koi pond and hot tub were easy to enjoy in a peaceful and private environment. We’ll be back!
Guest favourite
Chalet in Winhall
4.93 out of 5 average rating, 46 reviews

Le Chalet : beautiful renovated home - Stratton

CathyRating, 5 stars4 months ago
The best way I can explain our stay was that it felt like home. We are a family of six adults and four children ages 2-8. We spent most of our time on the top floor living area. The large kitchen island fit all ten of us, and we were able to eat all our meals together. The house was very clean and had everything we needed. There was a lot of snow on the property, so we were able to do some tubing in the backyard. It was a quick trip to Stratton Mountain each morning. Max was a great host. He ensured that the driveway was well plowed after a recent storm. He was quick to respond to any question, but we really did not need much help as everything was in order.
Guest favourite
Chalet in Winhall
4.89 out of 5 average rating, 81 reviews

Spacious Chalet W/ Endless Entertainment THE BARN

LukeRating, 5 stars1 month ago
We had a wonderful weekend at The Barn. Truly a comfortable and scenic space for us to relax and enjoy the weekend. Host was very responsive and everything worked as we expected. A great choice for a weekend away with a large group of friends easily accomodated.
Guest favourite
Chalet in Wardsboro
4.89 out of 5 average rating, 45 reviews

Indoor Hot Tub Chalet | Firepit Fun Near Mt Snow

AnneRating, 5 stars1 week ago
Great stay, would recommend to anyone looking for a VT retreat :)
Guest favourite
Chalet in Wardsboro
5 out of 5 average rating, 13 reviews

Modern Lux Cabin w/ Mtn Views | Fire Pit

AlexisRating, 5 stars3 weeks ago
We had the most amazing weekend getaway with a group of 12 close friends! The house was cozy, beautifully decorated, and felt like the perfect home away from home. Despite it being a rainy Memorial Day weekend, we had the best time just enjoying the space together. The backyard was stunning, a great place for walking out in the morning with your cup of coffee. The kitchen was a total highlight: spacious, well-stocked with everything we needed, and perfect for cooking and feasting with a group. This stay gave us such great memories, and we’re so grateful to the hosts for creating such a warm and welcoming space. Would absolutely recommend and hope to return someday!
Top guest favourite
Chalet in Winhall
5 out of 5 average rating, 27 reviews

Luxurious Fireside Lodge w/Stratton View

ChrisRating, 5 stars3 weeks ago
Had a group of 13 friends together for the long weekend and it was fantastic. The check-in and out process was smooth, the house was well organized and equipped with things you need for the kitchen, and plenty of firewood for the indoor and outdoor fireplaces. House was well done with a gigantic main room for everyone to hang out in, either on the comfortable couch and easy chairs, rocking chairs, dining table, or around the stunning kitchen island. Nice view of the mountains. Vermont surrounds are beautiful! Would come again!

Quick stats about chalet rentals in Jamaica

  • Total rentals

    10 properties

  • Nightly prices starting at

    $116 SGD before taxes and fees

  • Total number of reviews

    1.6K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Wifi availability

    10 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi and Pool

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Windham County
  5. Jamaica
  6. Chalet rentals