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Chalet vacation rentals in Jamaica

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Popular amenities for Jamaica chalet rentals

Family-friendly chalet rentals

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

Getaway in Green Mountains

AndrewRating, 5 stars3 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 favorite
Chalet in Plymouth
4.75 out of 5 average rating, 215 reviews

5BR Chalet in Historic Town bet Killington & Okemo

PamalaRating, 5 stars2 months 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 favorite
Chalet in Ludlow
4.82 out of 5 average rating, 76 reviews

Mountain Chalet + HOT TUB

ChristopherRating, 5 stars2 months ago
Great place to stay for okemo mountain!! Very close to local restaurants and the mountain
Superhost
Chalet in Granville
4.81 out of 5 average rating, 89 reviews

Hilltop Chalet on 20 rolling acres

PaulRating, 5 stars8 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, 452 reviews

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

KarenRating, 5 stars1 week ago
We had a great time at the cabin. Although there are other cabins on the property, it felt private. The space was very roomy and comfy. We loved the record player, and I looked at every record and played many of them! We took our own sheets and towels, but all that was at the cabin when we got there, so we didn't need them. It was nice to find empty kitchen cupboards for our own stuff, so we didn't have to rearrange everything :) And we've had a run of vacation rentals with foot high grass lately, so it was nice to see Jason mowing the lawn on our third day there. All in all, it was a great stay
Guest favorite
Chalet in Ludlow
4.95 out of 5 average rating, 128 reviews

Okemo Ski Chalet with Hot Tub

WillRating, 5 stars3 weeks 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 stars2 months ago
Our stay was fantastic. The house was conveniently located relative to Stratton mountain, very comfortable, and the host was fantastic
Top guest favorite
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

Guest favorite
Chalet in Dover
5 out of 5 average rating, 48 reviews

Authentic Vermont Chalet: Year Round Vacation Home

ChristinaRating, 5 stars3 months ago
Beautiful spot with a cozy yet spacious house. Instructions were very clear on how to get in and the different features of the house. Perfect for a relaxing get-away with friends!
Top guest favorite
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 favorite
Chalet in Charlemont
4.99 out of 5 average rating, 103 reviews

The Lodge on Warner Hill

MelissaRating, 5 stars3 weeks ago
We had an absolutely wonderful stay at this beautiful mountainside resort. The Lodge is peaceful, serene and incredibly relaxing—perfect for a weekend getaway. The home had plenty of space for our family, with comfortable beds that made for restful nights and enough space to have privacy. We especially loved the chef’s kitchen—it was fully equipped and a joy to cook in as a family. The outdoor space was fantastic, offering plenty of room to unwind and have fun together. We stayed here to celebrate our daughter’s college graduation, and it was the perfect backdrop for such a special occasion. Michelle was an amazing host—responsive, welcoming, and thoughtful throughout our stay. We highly recommend this property and are planning our return visit soon!
Top guest favorite
Chalet in Dover
5 out of 5 average rating, 35 reviews

Charming Mountain Chalet w/ Spa near Mt Snow

Caitlin Rating, 5 stars2 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 favorite
Chalet in Dover
4.98 out of 5 average rating, 63 reviews

A quintessential Vermont getaway

LauraRating, 5 stars3 months ago
Linda was awesome! She was super responsive and helpful. We ran into several snags with our trip due to weather but we kept in constant communication and it all worked out. The house is cute and has a certain charm to it. The hot tub wasn't working but that was communicated to us a day before so we were aware. The bathrooms are a bit small, particularly the showers. Overall we had a great trip. Very close to Mt Snow. Quiet and scenic location. Fireplace was nice to have. We replenished with kindling and dry wood just so we could keep a nice warm fire going. Lovely host & lovely home.
Guest favorite
Chalet in Winhall
4.89 out of 5 average rating, 80 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 favorite
Chalet in Dover
4.93 out of 5 average rating, 129 reviews

Hot Tub-Game Room-Fire Pit-Dogs Ok-8Min Mount Snow

MattRating, 5 stars1 month ago
Amazing house. Took my son for his 2nd birthday. They had a travel crib and a high chair ready for us. The house was clean and smelt amazing. They have everything you could think of in the kitchen to make your stay feel like home. Fee coffee with cream and sugar. They even had tea! The hot tub was wonderful clean and well maintained. We were so happy to make memories here on my boys birthday! Thank you again we will be back!
Guest favorite
Chalet in Wardsboro
5 out of 5 average rating, 13 reviews

Modern Lux Cabin w/ Mtn Views | Fire Pit

AlexisRating, 5 stars2 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!

Lakefront chalet rentals

Guest favorite
Chalet in Sunapee
4.94 out of 5 average rating, 81 reviews

Lake Sunapee Get Away

LaurieRating, 5 stars6 days ago
Thank you so much for a wonderful stay! The view was spectacular on every level! Lake Sunapee is a very special place, and meant a lot to be able to stay here. Excellent communication and very helpful instructions. The house is well equipped with everything. Beds are so comfortable. Plenty of room to spread out. Quiet and peaceful, loved looking at the lake! Thank you again so much for everything!
Top guest favorite
Private room in Bridgewater
4.99 out of 5 average rating, 172 reviews

MT Retreat / Killington, Woodstock, Rutland, Okemo

NicolaRating, 5 stars2 months 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 favorite
Chalet in Orange
5 out of 5 average rating, 27 reviews

Spectacular Lakefront 3br House, AC, private beach

DonnaRating, 5 stars8 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 stars3 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.

Quick stats about chalet rentals in Jamaica

  • Total rentals

    10 properties

  • Nightly prices starting at

    G$18,886 GYD 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

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  3. Vermont
  4. Windham County
  5. Jamaica
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