
Chalet holiday rentals in Jamaica
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Top-rated chalet rentals in Jamaica
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Popular amenities for chalet rentals in Jamaica
Family-friendly chalet rentals

Getaway in Green Mountains
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

Rustic Sunny Vermont Home near Mount Snow
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!

Mountain Chalet + HOT TUB
Great place to stay for okemo mountain!! Very close to local restaurants and the mountain

Hilltop Chalet on 20 rolling acres
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

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

Okemo Ski Chalet with Hot Tub
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.

Pickleball Pool Golf 7min-Stratton DogsOK Fire Pit
Our stay was fantastic. The house was conveniently located relative to Stratton mountain, very comfortable, and the host was fantastic

Cozy House - Mount Snow, VT
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

Authentic Vermont Chalet: Year Round Vacation Home
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!

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

Charming Mountain Chalet w/ Spa near Mt Snow
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!

A quintessential Vermont getaway
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.

Serene & Stylish Chalet + HOT TUB near Manchester
Garrett was responsive and allowed us to check in early as his Chalet was cleaned and ready for us early. Great host!! Welcome basket with hoodies and a host note to our group. Great!!

Spacious Chalet W/ Endless Entertainment THE BARN
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.

Summer Fun in Winhall! Family Game Room & Deck!
This was an enjoyable stay. Slept 6 comfortably. We also had such a great time in the game room playing pool, watching tv, and utilizing the arcade games. Totally recommend!

Wine Moose Hot tub Fireplace Sauna 9min to Mt Snow
Our family and friends took a trip to Mount Snow skiing and when I came across Tommy’s house it was everything we were looking for. The house was just as described, location was perfect and so was the house. Tommy was right there to help with any questions we had and was a real pleasure to work with. I would highly recommend this house to anyone!
Quick stats about chalet rentals in Jamaica
Total rentals
10 properties
Nightly prices starting at
₹7,715 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
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- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Pats Peak Ski Area
- West Mountain Ski Resort
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Mount Greylock Ski Club
- Berkshire East Mountain Resort
- Mount Sugarloaf State Reservation
- The Shattuck Golf Club
- Autumn Mountain Winery
- Dorset Field Club
- Baker Hill Golf Club
- Pineridge Cross Country Ski Area
- Clarksburg State Park
- Hildene, The Lincoln Family Home
- Ekwanok Country Club
- Brattleboro Ski Hill