
Vacation rentals in Jamaica
Find and book unique accommodations on Airbnb
Quick stats about vacation rentals in Jamaica

Total vacation rentals
Explore 220 vacation rentals in Jamaica

Nightly prices starting at
Jamaica vacation rentals start at G$4,180 GYD per night before taxes and fees

Verified guest reviews
Over 13,760 verified reviews to help you choose

Family-friendly vacation rentals
170 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
210 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!
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.

Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba
Summit view cottage boasts 3 acres in the beautiful green mountains, we are 1,700 feet up in elevation . At this brand newly built PET FRIENDLY cabin you will have 3 bedrooms and 2 full bathrooms, which will sleep 7 comfortably. We have a brand new 6 person HOT TUB! You will find yourself within 15 minutes to the world famous Stratton mtn, 15 minutes from Bromley mtn and a close 4 minutes to the local Magic mtn.Very close proximity to the town of Manchester, which has great shops and restaurants

Riverbed Treehouse @hot tub & a new sauna & views!
The beautiful & brand new Riverbed Treehouse with private sauna and a stunning new hot tub! Views all day long and wildly awesome sunsets!! Stratton mountain is right at your toes with a babbling brook turned raging river in the Spring! Beautiful woods & trails to explore. Stunning ridge line off the ski trails of Magic Mnt!! Close to town for quick shopping & coffee shops! Xcountry ski or snowshoe or walk our groomed trails!! FAST WiFi, nature lovers & a birdwatchers paradise!! @bentapplefarm

Private Apt on Farm, Hot Tub with views!
Your private 2-bedroom + loft apartment sits on a 38-acre Vermont farm with incredible views. Includes full kitchen, open living area, private entrance, and shared hot tub. Explore gardens, orchard, and heritage animals. Enjoy our Observatory with its historic 8½" Cooke telescope. https://www.airbnb.com/experiences/6812114?s=67&unique_share_id=f9d4ebb7-396a-4f65-9ed0-f2b464a4359c, Close to top ski areas—Stratton, Mount Snow, Magic, and Bromley. Sleeps 6, with an adjoining apartment available.

Beautiful Timber Frame Retreat
This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

The Chick Inn
This is a two-story, renovated barn adjacent to the chicken coop in rural Vermont with views of the forests. It has brand new floors, a new kitchenette, and fresh look. (Some renovation is still taking place.) The chicken coop is just next door but the birds are free-range and range they will. Enjoy a private, hot shower in the garden, just outside. This listing is only suitable for people comfortable with dogs, cats, and chickens which will undoubtedly greet you outside during your stay.

The Woodland A-Frame
Welcome to The Woodland A-Frame! Built in 1965, our cozy cabin is located 20 mins from Stratton Mountain & Mt. Snow, and 30 mins from Bromley, & Magic Mountain! Vermont is a four-season state, allowing guests to enjoy the cabin anytime of year. Whether it's for fall foliage, winter activities, spring festivals, or a summer at the lake, we are happy to host you anytime during the year to experience your ideal Vermont getaway! Dogs welcome with a $100 pet fee per pet (two dog max). No cats

Designer Chalet w/ Mountain Views close to it all
A perfect little getaway. This stylish 3 bedroom/2 bath chalet is surrounded by endless outdoor activities. Swimming, hiking, biking, visiting the local waterfalls, golf courses, or rent an ATV from local outfit. This beautiful home is perfect for 6-8 people. Situated on 2.5 acres, this private setting with mountain views, has everything you need to feel at home. Multiple restaurants, cafes, markets for food, beer & wine less than a 5 min drive as well to sporting stores for supplies.

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

Cozy Cabin at Frog Pond Farm
Cozy 500sq ft passive solar cabin on our small farm, 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/gardens or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.

Cottage-Swim-View-Firepit-7min to Stratton-Dog OK
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.

Classic Vermont A-Frame | Fire Pit | Near Stratton
Escape to a classic Vermont A-Frame in Jamaica, Vermont on a private wooded 3-acre property along scenic Route 100. Near Stratton Mountain, Mount Snow, Jamaica State Park, and Pike Falls, this peaceful mountain retreat is perfect for hiking, swimming holes, fall foliage, scenic drives, and outdoor adventures. Enjoy mornings on the screened porch and evenings around the fire pit listening to the river across the street under the Vermont stars.
Popular amenities for Jamaica vacation rentals
Other great vacation rentals in Jamaica

Air Conditioned Vermont Cozy Cabin near Stratton

Stratton Summer House | Trails + Swim Holes + AC

Log Cabin: Amazing Views, River Frontage, Hot Tub

2-Bedroom Home, 7 Minutes From Stratton Mountain

Artists Chalet minutes from Stratton Ski Resort

Artsy & Cozy Cabin - Renovated - River & VT skiing

Cozy Riverfront Home in beautiful Jamaica

Shiny Elk Chalet - near Mt Snow w/ cozy fireplace
When is the best time to visit Jamaica?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$80,042 GYD | G$80,042 GYD | G$61,442 GYD | G$45,768 GYD | G$47,022 GYD | G$44,723 GYD | G$48,276 GYD | G$47,022 GYD | G$47,022 GYD | G$52,247 GYD | G$51,411 GYD | G$76,280 GYD |
| 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.
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.
How much does it cost to stay in cabin rentals in Jamaica?
Experience the best of Jamaica with our cabin rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Jamaica have air conditioning?
Absolutely! We offer over 50 house rentals with air conditioning in Jamaica. Enjoy a tailored experience with all the comforts you desire.
Do cabin rentals in Jamaica have wifi?
Absolutely! We offer over 20 cabin rentals with wifi in Jamaica. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Jamaica have a bbq area?
Absolutely! We offer over 80 house 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.
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- Chalet rentals Jamaica
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- Family-friendly rentals Jamaica
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- Rentals with a fire pit Jamaica
- Rentals with a sauna Jamaica
- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Berkshire East Mountain Resort
- Pats Peak Ski Area
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Dartmouth College
- West Mountain Ski Resort
- Killington Resort
- Hildene, The Lincoln Family Home
- Fox Run Golf Club
- Bromley Mountain Ski Resort
- Mount Sunapee Resort
- Montshire Museum of Science
- Mount Monadnock
- Emerald Lake State Park
- Massachusetts Museum of Contemporary Art
- Camp Plymouth State Park
- Mount Greylock





