
Vacation rentals in Jamaica
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Top-rated vacation rentals in Jamaica
Guests agree: these stays are highly rated for location, cleanliness, and more.

Glamping Cabin with Hot Tub on Flower Farm
<b>Vermont's Most Wish Listed</b> ﹏﹏﹏ Nestled in a wooded grove on Tanglebloom Flower Farm, this unforgettable glamping-inspired farm stay invites you to escape the everyday & immerse yourself in nature - comfortably. Designed with a clear roof looking up to the trees and screened sides to let in the breeze, the handmade tiny cabin invites you to slow down. Explore southern Vermont's hikes, farmer's markets & swimming holes or stay put. Perfect for a romantic couples retreat or solo getaway.

Lawrence Cottage
Deep in the West River Valley region of Windham County, Lawrence Cottage is in a gorgeous and uncluttered setting upon Windham Hill. If you long for solitude, serenity and beauty, we have the perfect escape for you. We are convenient to all local amenities and activities and an easy drive from Boston or New York. We are near Townshend, Jamaica and Lowell Lake State Parks, Magic Mountain, Mount Snow and Stratton Mountain Resorts. This is Vermont--of course we welcome people of all backgrounds.

Vermont Botanical Studio Apartment
This room is one half of a floor in our studio building (35 sq m). It is the only occupied space in the building, which is separated from the main house by a yard. There is a queen-sized bed, full bath (no-curb shower), and an outdoor shower (not available in the winter) Small kitchen with a sink, fridge, 2-burner induction hob, microwave/convection oven, toaster, coffee pot, and cookware. Arched ceiling, with ceiling fan, large windows, deck, and Maggie's botanical art lining the walls.

New Cabin in Jamaica
Recently constructed 500sq ft passive solar cabin, 10 minutes to Stratton Mtn., 20 minutes to Mt. Snow and Dover for skiing, shopping, food, or a beer at Snow Republic. Quiet road but very accessible. Perfect area for hiking, biking, relaxing walks along the Ball Mountain Brook or kayaking on Grout Pond or Gale Meadows. Enjoy a campfire in the side yard/former pony corral or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.

Rustic Cabin in foothills of Green Mountains
Rennsli Cabin is off grid + nestled on a forested plateau in the foothills of the Green Mountains. You will feel like you are in the middle of nowhere, unplugged and able to regenerate. Kitchen is equipped with cooking essentials+ hosts provide water, coffee, tea, milk, fresh eggs + homemade soap. There is an indoor compostable toilet + outhouse + outdoor shower. Most seasons, the cabin is 100ft from parking, but weather conditions may require an 800 ft walk from parking at main house.

Yellow Sweetie at the Base of Stratton
Our adorable home, The Yellow Sweetie, is located in a convenient setting at the base of Stratton Mountain, just 1 minute to the Stratton Resort access road and 8 mins to the slopes. Explore Vermont's many historic towns with classic architecture and covered bridges, as well as its breathtaking mountains, rivers and lakes. The Yellow Sweetie offers stylish country living-meets-shabby chic comfort and coziness. Escape to the fresh Vermont mountain air where life feels a little bit simpler!

Sweet Vermont Tiny Home Get Away
Your unique Vermont retreat is just a click away! Come stay in this custom built tiny house in southern Vermont. We are an easy walk to the train station, art museum, restaurants, shops, and many beautiful nature spots in and around Brattleboro VT, plus a 40 minute drive to the Mount Snow ski area, and local hiking, swimming, boating, skiing, and skating opportunities. A nature lover's paradise! Enjoy the great outdoors and small town living, or cozy up in the tiny house and just relax.

The Getaway
Nestled in the woods but yet only; 10 min. (5.3 mls) to Stratton Mtn, 11 min. (7.6 mls) to Bromely Mtn, 26 min. (18.2 mls) to Magic Mtn, 33 min. (19.2 mls) to Mount Snow, 50 min. (38.2 mls) to Okemo and 68 min. (51.2 mls) to Killington. Also only minutes away from Southern Vermont golf resorts, Appalachian, Long and West River Trails, beautiful ponds rivers and falls, state parks, Manchester outlet shopping and the Equinox, fine dining and the most brilliant foliage in New England.

Apple Blossom Cottage: A Tiny House
The ABC is located just 15 minutes from the Stratton Mountain Gondola and just 2 miles from the popular Jamaica State Park. Comfortable for up to 5 people. The private tiny house includes fresh linens, dedicated Wi-Fi, a kitchenette, hot shower, flushing toilet, fire pit and porch. The calendar is accurate. Stratton Mountain Resort 10 miles Grace Cottage Hospital 7 miles Magic Mtn 15 miles Bromley 18 miles Mount Snow 15 miles Brattleboro 24 miles Okemo 30 miles Killington 47 miles

Inviting studio apartment above barn in Vermont
This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. I am as close or as far away as you would like me to be with my house right next door.

Charming studio in renovated 19th century church.
This spacious studio apartment is located in the former Swedish Congregational Church in historic Swedeville, a secluded hilly neighborhood built by Swedish immigrants in the 1800's. For years it housed Rick and Liza’s stained glass studio, which they have now lovingly and creatively transformed into a residence. The rental is minutes from the interstate and one mile from downtown Brattleboro, but the neighborhood has a rural and somewhat European flavor to it.

Cottage-7 min to Ski Stratton-Woodstove-View-DogOK
Authentic post & beam cottage surrounded by forest. Private location off a quiet road, 3 miles to Stratton Sun Bowl (a 7-minute drive). Nearby swimming hole at brook on property. Fire pit, propane BBQ, picnic table, spectacular Stratton Mountain view. Front porch & back porch with hammock, table & chairs. VCR/DVD & videos, boardgames & puzzles, kids toys, turntable & records, Satellite Internet & WiFi 20-100 mbps, TV & Roku. Gas heat, wood stove. Dog friendly.
Popular amenities for Jamaica vacation rentals
Other great vacation rentals in Jamaica

Charming Vermont Schoolhouse

Cozy Brookside Getaway

10 Min to Stratton Resort | Private Hot Tub

2-Bedroom Home, 7 Minutes From Stratton Mountain

Stratton A-Frame: Sauna Hot Tub EV Boot Warmers

Cozy Cottage Loft and Retreat

Cottage amongst the trees

The Woodland A-Frame
When is the best time to visit Jamaica?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ1,205 | ﺩ.ﺇ1,311 | ﺩ.ﺇ1,083 | ﺩ.ﺇ804 | ﺩ.ﺇ826 | ﺩ.ﺇ786 | ﺩ.ﺇ848 | ﺩ.ﺇ826 | ﺩ.ﺇ826 | ﺩ.ﺇ936 | ﺩ.ﺇ995 | ﺩ.ﺇ1,252 |
| Avg. temp | -5°C | -4°C | 1°C | 8°C | 14°C | 18°C | 21°C | 20°C | 16°C | 9°C | 4°C | -2°C |
Frequently Asked Questions
Are there pet-friendly vacation rentals in Jamaica?
Four-legged friends are welcome in Jamaica. Choose from more than 90 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Jamaica?
Yes! Work meets play with ease at over 100 vacation rentals in Jamaica featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in cabin rentals in Jamaica?
Experience the best of Jamaica with our cabin rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do chalet rentals in Jamaica have wifi?
Absolutely! We offer over 10 chalet rentals with wifi in Jamaica. Enjoy a tailored experience with all the comforts you desire.
Do cabin rentals in Jamaica have a bbq area?
Absolutely! We offer over 40 cabin rentals with a bbq area in Jamaica. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Jamaica have a gym?
Absolutely! We offer over 10 house rentals with a gym in Jamaica. Enjoy a tailored experience with all the comforts you desire.
Do chalet rentals in Jamaica have air conditioning?
Absolutely! We offer over 10 chalet rentals with air conditioning in Jamaica. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly cabin rentals in Jamaica?
Jamaica has more than 10 family-friendly cabin rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Quick stats about vacation rentals in Jamaica

Total vacation rentals
Explore 200 vacation rentals in Jamaica

Nightly prices starting at
Jamaica vacation rentals start at ﺩ.ﺇ73 per night before taxes and fees

Verified guest reviews
Over 12,580 verified reviews to help you choose

Family-friendly vacation rentals
160 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 90 rentals that welcome pets

Rentals with dedicated workspaces
100 properties have a dedicated workspace

Wi-Fi availability
190 of Jamaica vacation rentals include wi-fi access

Popular amenities for guests
Guests love Gym, BBQ grill, and Laptop-friendly workspace across Jamaica rentals

4.9 Average rating
Jamaica stays are highly rated by guests—averaging 4.9 out of 5!
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- Family-friendly rentals Jamaica
- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Pats Peak Ski Area
- Berkshire East Mountain Resort
- Magic Mountain Ski Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Pico Mountain Ski Resort
- Mount Greylock Ski Club
- West Mountain Ski Resort
- Mount Snow Ski Resort
- Mount Sugarloaf State Reservation
- Bromley Mountain Ski Resort
- Crotched Mountain Ski and Ride
- Whaleback Mountain
- Hildene, The Lincoln Family Home
- Hooper Golf Course
- Dorset Field Club
- Fox Run Golf Club
- Northern Cross Vineyard
- The Shattuck Golf Club




