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Compare 91 Chalets in Jamaica with updated reviews, rates, and availability.

Okemo Mountain Chalet W/ Hot Tub and Game Room
9.8 out of 10, Exceptional, (154)
"House was beautiful. Everyone enjoyed it. Host was very helpful and communicated very well. We're going to book our return next year, only issue was hot water ran out quickly affecting kids evening showers. "
Okemo Mountain Chalet W/ Hot Tub and Game Room
On Shuttle, 12 min walk to village. Late Check out. Private Baths
9.8 out of 10, Exceptional, (6)
"Great location and comfortable"
On Shuttle, 12 min walk to village. Late Check out. Private Baths
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
9.4 out of 10, Exceptional, (52)
"We had a fabulous time. "
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults
10.0 out of 10, Exceptional, (17)
"Stay was perfect"
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults
Beautiful Manchester VT Mountain Retreat w/Hot Tub
10.0 out of 10, Exceptional, (27)
"We really enjoyed our stay at this house. All the rooms were beautiful, clean and nicely decorated. The beds were very comfortable. Our dog loved the porch on the main floor. We will definitely book this house again, it is one of our favorites."
Beautiful Manchester VT Mountain Retreat w/Hot Tub
Green Mountain Manor - Ski and Summer Chalet
9.8 out of 10, Exceptional, (7)
"Relaxing VT stay . You are in a rural setting but places to stock up on supplies was less then 10 miniutes away . We watched the fireworks that stratton displayed pretty much from the comfort of the property .Our children are young adults and they had a blast finding local swimholes . As well as spending a day at Bromley Mountain ( 20 mins away ) where they did water slides , alpine slides , the giant swing to name a few . House is large and the ability to accomodate large families or groups ....
Green Mountain Manor - Ski and Summer Chalet
Brian Piece of Heaven for fall Foliage. Beautiful colors
9.8 out of 10, Exceptional, (26)
"Good place to stay with a well-equipped kitchen. It has a well lived-in feel, as opposed to a spotless modern hotel feel, so don't expect luxury. But it is homey and comfortable. Unfortunately, we had an issue with bees getting inside the apartment, and we had to leave early (I'm allergic). The host is working on resolving the problem. Host is very responsive and easy to work with."
Brian Piece of Heaven for fall Foliage. Beautiful colors
Expansive 7-BR Chalet 5-min from Mt. Snow
10.0 out of 10, Exceptional, (3)
"House is great, we had a large group. 2 living rooms, one with tv one without was a nice separation. To give some details on the layout, the bunk bed rm and twin room are off the living room on the main level, all other bd rooms are on the second floor. From the parking area to the main front door there are 31 steps.... not sure that was stated anywhere but hopefully everyone reads this review. I will stay here again if my group size demands it, it's close to mt snow, pretty secluded overall...
Expansive 7-BR Chalet 5-min from Mt. Snow
Serene & Stylish Chalet w/ HOT TUB near Manchester
10.0 out of 10, Exceptional, (9)
"We were very comfortable and relaxed, just what you want for a vacation. The property was clean and well appointed. We only lacked an outdoor outlet for charging our car. The host was in touch and helpful. We would stay here again."
Serene & Stylish Chalet w/ HOT TUB near Manchester
Classic Alpine Vermont Chalet
10.0 out of 10, Exceptional, (8)
"Fit the bill for our group of 8 skiing at Stratton for the weekend. Quirky decor and foosball table were a plus. Easy check in/check out"
Classic Alpine Vermont Chalet
Foliage view on private deck, family friendly, pet friendly, access to MOOver
2.0 star property
9.0 out of 10, Wonderful, (2)
"We spent the week, excellent location and the home was exactly as described in listing."
Foliage view on private deck, family friendly, pet friendly, access to MOOver
Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.
9.6 out of 10, Exceptional, (45)
"We had a very nice stay. The house had plenty of room for our family including the living, dining, and sleeping areas. The location was great."
Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.
Cozy Creekside Chalet centrally located near 4 ski resorts
10.0 out of 10, Exceptional, (7)
"We had the best time at this cozy spot with some friends for a weekend - highly recommend!"
The price is AED 915
AED 2,098 total
includes taxes & fees
14 Oct - 15 Oct
Cozy Creekside Chalet centrally located near 4 ski resorts
Summer Adventures Await -- Book now for the Horse Show & Explore Manchester
10.0 out of 10, Exceptional, (48)
"My family and I had a great stay at the Skylight Lodge. It is very different from other rentals, being a former inn. There is plenty of space for a big group and the two master suites are great. The fireplace in the main room is like something out of game of thrones, and was the highlight of the trip for the adults. The kids spent most of the time playing games in the second living room on the first floor. The house is also very conveniently located near Manchester. We would definitely come...
Summer Adventures Await -- Book now for the Horse Show & Explore Manchester
New-Crown Jewel at Mount Snow-Ski-on/off
New-Crown Jewel at Mount Snow-Ski-on/off
Sunny Stratton Mountain Retreat: 5BD Modern Oasis w/Hot Tub, Pond, & BBQ Deck
9.4 out of 10, Exceptional, (6)
"We were absolutely thrilled to experience a fresh powder drop during our stay, which was a delightful surprise in an otherwise dry season. The house surpassed all our expectations, providing the perfect haven for our large group. It was impeccably clean, incredibly warm, and featured an abundance of comfortable beds, all while being conveniently close to the mountain. A standout feature for us was the Tesla charger in the garage, which met our specific needs perfectly. We are already eagerly...
The price is AED 1,095
AED 3,076 total
includes taxes & fees
30 Sep - 1 Oct
Sunny Stratton Mountain Retreat: 5BD Modern Oasis w/Hot Tub, Pond, & BBQ Deck
8 minutes to Mount Snow skiing, Hot Tub, Fire Pit, Game Room, Dog Friendly
10.0 out of 10, Exceptional, (14)
"Great place to stay! Very roomy, everything was nice and clean! We had an amazing weekend!"
The price is AED 896
AED 2,561 total
includes taxes & fees
20 Oct - 21 Oct
8 minutes to Mount Snow skiing, Hot Tub, Fire Pit, Game Room, Dog Friendly
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails
10.0 out of 10, Exceptional, (33)
"The home was well appointed with all the amenities and plenty of room for our three families (6 adults and 6 kids). The game room downstairs and open concept living room were awesome and would have been used more often had the weather not been so perfect. The property is truly the star of this place, picturesque mountain views and an amazing fire pit. We will definitely be renting again."
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails
Cozy Chalet on Magic Mountain
10.0 out of 10, Exceptional, (7)
"My wife and I had a great stay at the chalet this past weekend. The property was exactly as described and very well maintained. We would absolutely stay here again!"
Cozy Chalet on Magic Mountain
4BR / 3BA Smart Home w/ Hot Tub, Mountain View Ski Chalet 3 minutes to Stratton
9.2 out of 10, Wonderful, (19)
"As a yearly VRBO renter I am accustom to renting a few houses and this one had some disappointing takes and some great attributes. First the houses layout and location is great for a large get together and the views are amazing! But apon arriving you could first tell the slate entry way and door knob was in need of repair. From there we had a few other dissapointments, the dishes were dirty, scattered about the kitchen. Towels were damp and we later learned why, it was because the dryer simply...
4BR / 3BA Smart Home w/ Hot Tub, Mountain View Ski Chalet 3 minutes to Stratton
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Jamaica

Green Mountain Modern House: iconic modern getaway
Green Mountain Modern House: iconic modern getaway
Long Trail House at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very Good, (72)
"The unit was perfect for our ski race weekend. Very accessible, underground parking included (ski boxes on top of SUVs will not fit - thankfully we left ours at home), really nice place with everything we needed!"
Long Trail House at Stratton Mountain Resort
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
9.6 out of 10, Exceptional, (189)
"Cabin was beautiful, wife loved the decor of the cabin. They had everything we needed onsite for a wonderful stay."
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.