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Jamaica Vacation Rentals

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Vacation Rentals in Jamaica

Spacious Vermont Ski House...stratton, Mt.snow, Okemo & Bromley Area

Spacious Vermont Ski House...stratton, Mt.snow, Okemo & Bromley Area

3659 S Hill Rd, Jamaica, VT

Located in Jamaica, this family-friendly holiday home is 0.5 mi (0.7 km) from Jamaica State Park, and within 6 mi (10 km) of Ball Mountain State Park and Ball ...

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 4 bed With Shuttle & Rec Room

Stratton 4 bed With Shuttle & Rec Room

67 Fox Hollow Rd, 67, Jamaica, VT

This family-friendly Jamaica holiday home is within 3 mi (5 km) of Stratton Mountain Golf Course and Jamaica State Park. Stratton Mountain Resort and Stratton ...

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
Cozy ski Home With Amazing Views of Stratton & Bromley Mountains

Cozy ski Home With Amazing Views of Stratton & Bromley Mountains

84 Todd Hill Rd, Jamaica, VT

Situated in Jamaica, this holiday home is 2.5 mi (4 km) from Stratton Mountain Golf Course and within 6 miles (10 km) of Stratton Mountain Resort and Jamaica ...

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 Mountain: Luxury Contemporary Country Home

Stratton Mountain: Luxury Contemporary Country Home

217 Strattongate Road, Jamaica, VT

This family-friendly Jamaica holiday home is located in the mountains, 1.7 mi (2.8 km) from Jamaica State Park, and within 6 mi (10 km) of Stratton Mountain ...

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
A Green Mountain Escape: Outdoor Adventures Await!

A Green Mountain Escape: Outdoor Adventures Await!

121 Stratton Gate Rd, Jamaica, VT

This family-friendly Jamaica chalet is located in the mountains, within 3 mi (5 km) of Jamaica State Park and Ball Mountain Dam. Ball Mountain State Park and ...

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!
Green Mountain Tiny House

Green Mountain Tiny House

26 Howe Farm Rd, adjacent to the barn, Jamaica, VT

Situated in the mountains, this holiday home is within 6 miles (10 km) of Jamaica State Park, Ball Mountain Dam and Ball Mountain State Park. Townshend State ...

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
Two Bedroom Chalet, Charming, Quiet, River Front

Two Bedroom Chalet, Charming, Quiet, River Front

1647 Pikes Falls, Jamaica, VT

This family-friendly Jamaica chalet is located on the riverfront, 2.4 mi (3.9 km) from Jamaica State Park, and within 6 mi (10 km) of Stratton Mountain Resort ...

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
New Listing - The Overlook VT by Stratton Mountain

New Listing - The Overlook VT by Stratton Mountain

3011 Vt Route 30, Jamaica, VT

Situated in the mountains, this apartment building is 1.1 mi (1.7 km) from Jamaica State Park and within 6 miles (10 km) of Ball Mountain Dam and Ball Mountain ...

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
Stratton Mountain Getaway w/ Spectacular Views - New Listing!

Stratton Mountain Getaway w/ Spectacular Views - New Listing!

15 Nearing Rd, Jamaica, VT

Located in Forest Farms, this holiday home is 2.9 mi (4.6 km) from Stratton Mountain Golf Course and within 6 miles (10 km) of Stratton Mountain Resort and Stratton ...

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!
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See all available properties in Jamaica
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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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Jamaica. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Jamaica?
Yes, there are vacation rentals close to well known attractions in Jamaica, or you can select a more remote option if you’d like a relaxing place to stay. Jamaica is known for its mountain views and art. Make sure you have time to check out the monuments while you’re in the area.
What can I see and do in Jamaica?
Jamaica State Park and Ball Mountain State Park are a couple of lovely local spots to get outside and enjoy nature. You’ll find favorite places to visit like Stratton Mountain Resort and Mount Snow in the larger area.
What are vacation rentals like in Jamaica?
Vacation rentals are private properties you can stay in for a few days or a quick weekend in Jamaica. Vacation rentals feature extras like laundry facilities and kitchens so you’ll feel right at home. If you’re concerned about a clean environment, a vacation rental can offer a sense of security away from public hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You’ll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for a small group gathering.

Other types of properties in Jamaica you may be interested in

Cold Moon Farm Bed and Breakfast

Cold Moon Farm Bed and Breakfast

2.5 out of 5
251 Pratt Bridge Road, Jamaica, VT
Cold Moon Farm Bed and Breakfast
Spacious Vermont Ski House...stratton, Mt.snow, Okemo & Bromley Area

Spacious Vermont Ski House...stratton, Mt.snow, Okemo & Bromley Area

3659 S Hill Rd, Jamaica, VT
Spacious Vermont Ski House...stratton, Mt.snow, Okemo & Bromley Area
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.