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Chalet holiday rentals in Jamaica

Find and book unique chalets on Airbnb

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Popular amenities for Jamaica chalet rentals

Family-friendly chalet rentals

Guest favourite
Chalet in Peru
4.9 out of 5 average rating, 63 reviews

Getaway in Green Mountains

AndrewRating, 5 stars2 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
Superhost
Chalet in Plymouth
4.75 out of 5 average rating, 215 reviews

5BR Chalet in Historic Town bet Killington & Okemo

PamalaRating, 5 stars1 month ago
We had an issue with our previous rental and needed to find a place to stay that is pet friendly and available. Rad and Carol responded quickly to our reservation request. The house was made available to us early in the day and hot tub prepped last minute for us to enjoy! The Chalet is beautiful and spacious, the location is private and relaxing. The wood stove kept us warm and cozy while we enjoyed watching light snow fall. We would definitely stay there again and bring our family with us!
Guest favourite
Chalet in Wilmington
4.95 out of 5 average rating, 98 reviews

Rustic Sunny Vermont Home near Mount Snow

AndreaRating, 5 stars2 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 stars1 month ago
Great place to stay for okemo mountain!! Very close to local restaurants and the mountain
Superhost
Chalet in Killington
4.87 out of 5 average rating, 75 reviews

West Park Chalet at Killington: Great For Groups!

DarleneRating, 5 stars1 month ago
We had a such a great time staying at Ed's property. Super close to the mountains - we went snowboarding every day, it was great! Ed was very responsive, and the house was kept clean. We really enjoyed the hot tub after a long day of snowboarding. Would highly recommend for big groups. Plenty of bed space.
Superhost
Chalet in Granville
4.81 out of 5 average rating, 89 reviews

Hilltop Chalet on 20 rolling acres

PaulRating, 5 stars6 months ago
My wife and I thoroughly enjoyed our stay at John's Chalet. The house was exactly as described beautiful inside and out. We loved seeing all the wildlife around the home every day. The home is very private and close to many outdoor activities especially hiking. We would certainly consider this home again on our next trip to Vermont. Sincerely Paul & Rebecca
Superhost
Chalet in Jamaica
4.78 out of 5 average rating, 445 reviews

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

OscarRating, 5 stars1 week ago
Beautiful place, real quaint and nice to stay at. The surroundings were real nice at nice and the nature was very nice to be surrounded by. All the amenities worked as expected and the beds were comfortable. The porch was our favorite place to relax at; hammock, yard, stereo playing from inside. Great stay … thanks Jason and Sara :))))
Superhost
Chalet in Wilmington
4.57 out of 5 average rating, 91 reviews

Cozy House - Mount Snow, VT

VincyRating, 5 stars3 months ago
Mariah’s cabin was perfect for our getaway. Lots of natural light, clean and had everything we needed. It was a quick drive to Mt Snow and close to some cute restaurants in Wilmington. I was given clear and very lengthy instructions for check in/check out and Mariah was responsive to some minor questions we had throughout our stay. I missed the opportunity to book the hot tub/clubhouse when we first made the reservation. Hoping future guests don’t make the same mistake and be sure to request it at the time of booking!

Luxury chalet rentals

Guest favourite
Chalet in Dover
5 out of 5 average rating, 15 reviews

Gorgeous Mt. Snow 3 bedroom chalet

MikeRating, 5 stars2 months ago
Great place, nice and clean ,close to Mt Snow. Definitely a place I would stay again.
Top Guest favourite
Chalet in Dover
4.97 out of 5 average rating, 110 reviews

Mountain Chalet: Private Brook - Hot Tub - Firepit

EricRating, 5 stars1 month ago
Family had a great stay at Danielle and Ben’s the house was very clean and kid friendly and we really enjoyed having the view of the creek from decking area. Very close to Mt Snow and surrounding area restaurants and attractions. Would stay again.
Top Guest favourite
Chalet in Charlemont
4.99 out of 5 average rating, 100 reviews

The Lodge on Warner Hill

MichaelRating, 5 stars1 week ago
My friends and I had a wonderful stay at this Airbnb! The space was impeccably clean, making us feel right at home from the moment we arrived. It was incredibly quiet and peaceful, perfect for relaxing and unwinding. The surroundings were rustic and beautiful, adding to the overall charm of the stay. The host was thoughtful and attentive, ensuring everything was perfect. I highly recommend this place to anyone looking for a serene and spotless getaway!
Guest favourite
Chalet in Winhall
4.92 out of 5 average rating, 36 reviews

1970's Classic Ski Chalet - Stratton Mountain

CaraRating, 5 stars2 months ago
The 70’s chalet is its name sake! Cozy and close to the mountain. The fireplace and downstairs room make it a great after ski relaxation spot! And it’s 5 minutes to Stratton Mountain!
Guest favourite
Chalet in Dover
4.93 out of 5 average rating, 44 reviews

New! Custom Chalet minutes from Mt Snow w/ Hottub

ZacharyRating, 5 stars2 months ago
The house was fantastic. Great condition, cool layout! There was a ton of snow, and the property was well plowed, shoveled and sanded!
Superhost
Chalet in Winhall
5 out of 5 average rating, 9 reviews

4+BR pet-friendly w/ hot tub & Stratton parking!

YairRating, 5 stars2 months ago
Great house, as described. Very responsive host before and during the stay with clear instructions. The couple of things that stood out: 1. Big house; easily sleeps 10, can get a couple more kids in if you want. 2. 15 minutes to Stratton with a parking permit provided which was key. 3. Indoor garage space was great, especially as it was snow storming outside. Kitchen had everything you'd want. Snow was plowed early in the morning. Stayed with wife and 2 teenage daughters and 2 dogs. Would come back. Thank you!
Guest favourite
Chalet in Wardsboro
4.88 out of 5 average rating, 43 reviews

Indoor Hot Tub Chalet | Firepit Fun Near Mt Snow

KellyRating, 5 stars1 month ago
We really enjoyed our stay! The house is beautiful and perfect location for skiing at Mt snow or Stratton. Indoor hot tub was a huge hit & spacious living spaces were great for spending quality time together!
Guest favourite
Chalet in Winhall
4.96 out of 5 average rating, 95 reviews

Minutes to Stratton! Large, private home w. sauna

AliciaRating, 5 stars2 months ago
We had a wonderful stay at Zach and Tasha’s place. Perfect house for our 2 families with kids. Close to Stratton Mountain. Very clean house and well equipped. The sauna was our favorite part! Will come back for sure!

Lakefront chalet rentals

Top Guest favourite
Private room in Bridgewater
4.99 out of 5 average rating, 172 reviews

MT Retreat / Killington, Woodstock, Rutland, Okemo

NicolaRating, 5 stars1 month ago
Linda and Ted are very welcoming hosts and have a beautiful home. We had a great weekend and would definitively consider going back.
Top Guest favourite
Chalet in Orange
5 out of 5 average rating, 27 reviews

Spectacular Lakefront 3br House, AC, private beach

DonnaRating, 5 stars7 months ago
OMG Beautiful! Walking into the gorgeous house, we didn't know whether to look inside or outside first! The inside is lovely, clean and neat without unnecessary clutter. The outside is spacious and beautiful. The house and property were described perfectly. Washer & dryer worked well. The pool table downstairs could easily be used without waking anyone in the house. When the owner learned we would be traveling with an infant, she made sure to have a highchair, crib, and infant life jacket in the house. The house is safe for babys. There isn't space to list all that we loved about this house. It has become part of our reunion week wonderful memories. Did I mention that the house was spotless and the grounds immaculate (except for the falling leaves which was part of the beauty!) I would happily stay here again and again and again.
Chalet in Ludlow
4.76 out of 5 average rating, 128 reviews

Charming Lakefront House

EricaRating, 5 stars2 months ago
This home was just what we were looking for. It is charming and spacious, rustic in all of the right ways, with a gorgeous view of the lake, and so close to Okemo. The master bedroom was huge, and we really enjoyed the large communal space with the wood-burning stove. Some of us were cooking while others were playing games, while others were relaxing by the fire, so that we could all easily enjoy each other‘s company. It was the perfect spot for a ski getaway. We all agreed we would love to stay there again.
Superhost
Chalet in Winchester
4.85 out of 5 average rating, 122 reviews

Chalet Sonsie: A Sweetwater Stay

SarahRating, 5 stars2 weeks ago
Absolutely amazing stay!! So peaceful and relaxing. Not too much nearby, which honestly was a good thing - allowed us to relax and unwind from the every day grind! Our son, age 5, absolutely loved playing in the Arcade!! We got in some fishing on the dock and watched movies by the fireplace at night. Just stunning. Exactly what we needed as a small family. Could not have asked for anything more. We WILL be back again soon!

Quick stats about chalet rentals in Jamaica

  • Total rentals

    10 properties

  • Nightly prices starting at

    $140 AUD before taxes and fees

  • Total number of reviews

    1.6K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Wi-Fi availability

    10 properties include access to Wi-Fi

  • Popular amenities

    Kitchen, Wi-Fi and Pool

Destinations to explore

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  3. Vermont
  4. Windham County
  5. Jamaica
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