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Two Bedroom Chalet, Charming, Quiet, River Front
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0.96 km from city centre
4.3/5Excellent! (15 reviews)
Breathtaking Tranquility!!

"Do you want some quite time? A cozy fire while you watch the river flow just outside?.. Then you'll love this place!! It's so close, but it feels so far..talk about off the grid, (Verizon gets NO service here). Great winter getaway!!!! in the background"…"

Reviewed on Jan. 29, 2020

Two Bedroom Chalet, Charming, Quiet, River Front
Family Home, 5 Minutes to Stratton Mountain!
35 Sugarbush Drive, Jamaica, VT
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5.95 km from city centre
5/5Exceptional! (3 reviews)
Beautiful House!

"We really enjoyed the property. It was beautiful, clean, and spacious for all. Would love to stay there again. A++"…"

Reviewed on Oct. 18, 2019

Family Home, 5 Minutes to Stratton Mountain!
Cozy ski Home With Amazing Views of Stratton & Bromley Mountains
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6.5 km from city centre
4.8/5Exceptional! (6 reviews)
All you could ask for in a VT mountain getaway

"Allison's property came exactly as advertised - breathtaking views and a homey live in feeling. We loved spending time on the deck during the day and cozying up inside at night. This is the perfect place for a medium to large sized group who is looking to be up amid the trees."…"

Reviewed on Oct. 21, 2020

Cozy ski Home With Amazing Views of Stratton & Bromley Mountains

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Stratton 4 bed With Shuttle & Rec Room
67 Fox Hollow Rd, 67, Jamaica, VT
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7.62 km from city centre
5/5Exceptional! (1 review)
Great house. Great location!

"We loved our stay. The house is cozy and clean and has plenty of space. It is deceptively large. The sleeping situation is great with more than enough room for 10 people. The foyer area is great for all the boots and snowwear we had so we could stay organized and not clutter up the house with our ..."…"

Reviewed on Jan. 4, 2019

Stratton 4 bed With Shuttle & Rec Room
Stratton Mountain Getaway w/ Spectacular Views - New Listing!
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5.49 km from city centre
5/5Exceptional! (13 reviews)
Leaf peeping get away

"Carrie's house is beautiful house with great views!!! We could see the early snow up on Stratton Mt trails... got this old skier's heart pumping! My first impression when I walked in was that the house was smaller then what I expected, but the flow of space and the large window was wonderful. The ..."…"

Reviewed on Oct. 21, 2020

Stratton Mountain Getaway w/ Spectacular Views - New Listing!
Cozy 4 Bedroom, Fully Equipped/vacation Condo
73 Pond View Rd, 73, Jamaica, VT
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7.62 km from city centre
5/5Exceptional! (1 review)
Great long ski weekend!

"This was a perfectly sized property for 2 families. There was plenty of space to spread out, and the owner was very responsive. It was clear that her priority was for us to be comfortable in her home."…"

Reviewed on Feb. 27, 2020

Cozy 4 Bedroom, Fully Equipped/vacation Condo
Renovated chalet w/ stunning views, vaulted ceilings
Jamaica Townhome w/ Pool - Mins to Stratton Mtn!
107 Lower Bear Lane, Jamaica, VT
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5.63 km from city centre
Jamaica Townhome w/ Pool - Mins to Stratton Mtn!
New Listing - The Overlook VT by Stratton Mountain
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3.37 km from city centre
5/5Exceptional! (1 review)
Perfect ski getaway

"Amazing experience from start to finish. Paul (host) has the place is perfect shape and even helped us out with a couple lift vouchers for Stratton to save some money on tickets. Close proximity to 3+ ski resorts and a perfect condo style place with every detail thought through carefully, including ..."…"

Reviewed on Mar. 11, 2020

New Listing - The Overlook VT by Stratton Mountain
Spacious Vermont Ski House...stratton, Mt.snow, Okemo & Bromley Area
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2.38 km from city centre
5/5Exceptional! (2 reviews)
Family perfect

"Everything was perfect. When we walked into the house we were thrilled to find it was even better than expected. Very clean and more spacious than anticipated. Very comfortable for 10 people. Everything we needed in the kitchen. We enjoyed the beautiful fireplace and the little town at the bottom ..."…"

Reviewed on Oct. 27, 2019

Spacious Vermont Ski House...stratton, Mt.snow, Okemo & Bromley Area
Stratton Mountain: Luxury Contemporary Country Home
217 Strattongate Road, Jamaica, VT
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2.12 km from city centre
4.7/5Exceptional! (3 reviews)
Ski House in the summer

"This is a ski house that we stayed in during the summer, it was close enough to the village of Jamaica and good swim spots that it worked well for us. The ping pong table was a big hit with the kids."…"

Reviewed on Aug. 18, 2020

Stratton Mountain: Luxury Contemporary Country Home
Green Mountain Tiny House
26 Howe Farm Rd, adjacent to the barn, Jamaica, VT
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5.48 km from city centre
5/5Exceptional! (1 review)
Great Tiny House!

"This place was ADORABLE!!!!! The edison lights outside were awesome in the snow!! They had dry wood for a campfire outside, and the whole place heated up really fast! They had great communication and great references for around the area!!! Thanks for a great stay!!!!!!"…"

Reviewed on Feb. 21, 2020

Green Mountain Tiny House
A Green Mountain Escape: Outdoor Adventures Await!
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2.95 km from city centre
5/5Exceptional! (2 reviews)
Wonderful ski vacation

"House was perfect for 2 families with plenty of room for all. Great location and enjoyed relaxing by the fire each evening."…"

Reviewed on Mar. 1, 2020

A Green Mountain Escape: Outdoor Adventures Await!
4 Bedroom/3 Bath Stratton Townhouse
1 Pond View Rd, Jamaica, VT
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7.26 km from city centre
5/5Exceptional! (4 reviews)
Amazing Stay

"We loved everything about our stay. The accommodations were top notch and the activities in the area were amazing. We did a different lake every day, hikes, and biked. Vermont is so beautiful, lush, and green during the summer."…"

Reviewed on Aug. 16, 2020

4 Bedroom/3 Bath Stratton Townhouse
Three Mountain Inn
3.5 out of 5
3732 Vermont Routes 100 and 30, Jamaica, VT
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2.69 km from city centre
4.9/5Exceptional! (15 reviews)

"We had a wonderful experience staying here. We started here the first weekend in MARCH 2020. We decided to go skiing at STRATTON and found this place to be in a perfect location!! The Inn is very nice, clean and the details are superb! Such a nice place to stay! So cozy too! Major plus : Many restaurants ..."…"

Reviewed on Mar. 10, 2020

Three Mountain Inn
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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.

Jamaica Hotel Guide

Looking for a hotel or apartment in Windham County, particularly in or near Jamaica? Jamaica features 3 quality accommodation options within a 0.1-kilometre (0.06-mile) radius of the center of town.

Accommodations that are fairly close to the city center of Jamaica include the Three Mountain Inn and Cold Moon Farm Bed and Breakfast.

You could check out the Long Trail House and also the The Equinox, a Luxury Collection Golf Resort & Spa, Vermont. The Long Trail House is located 8 kilometres (5 miles) from the main part of Jamaica. The The Equinox, a Luxury Collection Golf Resort & Spa, Vermont, is positioned 20 kilometres (14 miles) away. Two more accommodation options worth checking out around Jamaica include the Vantage Point Villas and the Inns at the Equinox.

Wilmington is found 35 kilometres (21 miles) to the southeast of Jamaica. While here, you can explore the Brattleboro Country Club. Brattleboro is blessed with a range of good Expedia-listed accommodations. Why not visit Wilmington, where you can explore the Haystack Golf and Country Club. Wilmington is 25 kilometres (16 miles) to the south of Jamaica. Expedia-listed accommodations in Wilmington include the White House Inn and Wilmington Inn & Tavern.

Before you leave Windham County, make sure you experience some local sport. Visit Times Union Center to the southwest of Jamaica. For visitors who are interested in sleeping nearby, make a reservation in the Hilton Albany or TownePlace Suites by Marriott Albany Downtown/Medical Center.

Thank you for checking out our Jamaica hotels and apartments. Now, why not spend a few minutes exploring Expedia's Jamaica travel guide for the low-down on this area's many things to see and do.

Frequently asked questions

Where is the best place to stay in Jamaica?
Based on our traveler data, Cold Moon Farm Bed and Breakfast is one of the top choices for your stay. This B&B offers free breakfast and free WiFi. Three Mountain Inn is another good option for your trip.
If I need to cancel my hotel reservation in Jamaica, will I receive a refund?
Yes! Most hotel bookings are refundable if you cancel before the hotel’s cancellation deadline, which often is within 24-48 hours of check in. If you have a reservation that’s non-refundable, it may still be possible to cancel it and receive a refund within 24 hours of your booking. Add dates, click “Search”, then filter by “free cancellation” to get the top deals on offer in Jamaica.
What's the best hotel for a family vacation to Jamaica?
Cold Moon Farm Bed and Breakfast is a B&B with free parking and free breakfast, and it’s a top choice on Expedia for families. Attractions in the area like Orvis Fly Fishing and The Nature Museum are also fun for kids of all ages.
What's the best hotel for a romantic getaway to Jamaica?
Three Mountain Inn is a favorite 3.5-star inn for couples, and features rainfall showerheads and a bar.
What's the best hotel to stay near the slopes in Jamaica?
Based on our travel data, Cold Moon Farm Bed and Breakfast is a top B&B for hitting the ski slopes, and features free breakfast and free WiFi. Three Mountain Inn is another good option for your ski trip. Spend your days on the slopes by visiting Stratton Mountain Resort, Mount Snow, or Magic Mountain Ski Resort.

Recent Reviews in Jamaica

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