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Jamaica vacation rentals

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Top-rated vacation rentals in Jamaica

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Cabin in Londonderry

4.94 out of 5 average rating, 334 reviews

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery & hiking right outside your front door. The Cabin has an open floor plan with a full bath, galley kitchen & dining/living area with pullout futon couch that converts into a 2nd bed. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

Cabin in Jamaica

4.89 out of 5 average rating, 369 reviews

Forest Cabin-Swim-Views-Fire Pit-7 min to Stratton

Authentic post & beam cabin surrounded by forest. Private location off a quiet road, 3 miles to Stratton Sun Bowl (a 7-minute drive). Swimming hole at babbling brook on property, fire pit, hammock on porch, propane BBQ, picnic table, forest views. VCR & videos, turntable & records, games, Satellite Internet & WiFi 20-100 mbps, TV & Roku. Staircase to loft, gas heat, wood stove, pellet stove. Full kitchen. Easy to use, odorless composting toilet. Dog friendly (sorry, no cats due to allergies).

Tiny home in Wilmington

4.99 out of 5 average rating, 203 reviews

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!

Cabin in Jamaica

5 out of 5 average rating, 215 reviews

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.

Cabin in Newfane

4.95 out of 5 average rating, 148 reviews

Cozy Cabin in Southern VT

Take it easy at this tranquil getaway. Fall asleep to chirping bugs and wake up to birdcalls. This is a quiet, lovely cabin in Newfane VT. Read a book, walk the meditation circle, swing in the hammock, and explore all that Southern VT has to offer. Close to swimming holes, hikes, country stores, flea and farmers' markets, and ski mountains (Mt Snow and Stratton) Pets and children are welcome, but there is only one queen bed. We can usually provide a travel crib if requested in advance.

Guesthouse in Jamaica

4.95 out of 5 average rating, 154 reviews

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.

Chalet in Jamaica

4.98 out of 5 average rating, 241 reviews

Vermont Chalet

Escape to our cozy A-frame on 3 private acres in Southern Vermont for a peaceful, secluded retreat. Relax to the soothing sounds of the river across the street while unwinding on the covered, screened-in porch. Enjoy a fully stocked kitchen, updated bathroom, strong WiFi, video games and books by a warm wood stove. Explore local towns, hike, or wander through our tranquil forest. With an EV charger, local artisan soaps, and warm woodstove, this is the perfect spot for a serene getaway.

Rental unit in Jamaica

4.85 out of 5 average rating, 201 reviews

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.

Home in Jamaica

4.86 out of 5 average rating, 277 reviews

Yellow Sweetie at the Base of Stratton

Our adorable home, The Yellow Sweetie, is located in a quiet 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!

Barn in Chester

4.99 out of 5 average rating, 571 reviews

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. We are as close or as far away as you would like us to be with our house right next door.

Guest suite in Newfane

4.93 out of 5 average rating, 200 reviews

Cute studio apt on historic VT farm

Spend some time on a historic farm in Southern Vermont. Visit with pigs and chickens, walk around on country roads, take a dip in swimming holes, wildlife abounds! Super-relaxing setting in beautiful Mother Nature and well-equipped accommodations with everything you need. The self-contained little studio has a separate entrance. Full kitchen and bath, queen bed plus a roll-out twin. Excellent heater. Wifi is enough for basic tasks, but not for 8 hours of daily zoom.

Guesthouse in Putney

4.97 out of 5 average rating, 263 reviews

Cozy cottage loft and retreat

Returning guests, please ask about our discount! Relax and recharge in our peaceful Vermont cottage. Enjoy this sweet getaway with hardwood floors, fast wifi, a fully equipped kitchen, a quiet sleeping loft with a queen size bed, gorgeous natural light, views of surrounding hills and pond, gardens, and your own private entrance and back deck next to the Putney Brook.

Vacation rentals for every style

Get the amount of space that is right for you

Chalets

Adventure-ready homes with après-ski style

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space thats all yours, with room for everyone

Popular amenities for Jamaica vacation rentals

Laptop-friendly workspace

Air conditioning

Stay near Jamaica's top sights

Jamaica State Park134 locals recommend

Honeypie122 locals recommend

Winhall Market38 locals recommend

Workhorse Cafe35 locals recommend

Ungrounded Coffee Roasters27 locals recommend

Hamilton Falls27 locals recommend

Other great vacation rentals in Jamaica

Rental unit in Winhall

5 out of 5 average rating, 12 reviews

Private & Quiet Apartment near Stratton Access Rd

Home in Jamaica

5 out of 5 average rating, 31 reviews

2-Bedroom Home, 7 Minutes From Stratton Mountain

Tiny home in Jamaica

5 out of 5 average rating, 11 reviews

Tiny home! 5 min to Stratton. 1 min to Pikes Falls

Cabin in Jamaica

5 out of 5 average rating, 37 reviews

Wishing Well Cabin

Home in Londonderry

4.98 out of 5 average rating, 112 reviews

Modern 3-bedroom A-frame in Londonderry w/ Pond

Condo in Dover

5 out of 5 average rating, 51 reviews

Four Seasons Slope-side Getaway at Mount Snow

Cabin in Wardsboro

4.85 out of 5 average rating, 96 reviews

Mountain side acres

Cabin in Stratton

5 out of 5 average rating, 20 reviews

Modern Cabin in Stratton

Quick stats about vacation rentals in Jamaica

Total rentals
210 properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
13K reviews
Family-friendly rentals
180 properties are a good fit for families
Pet-friendly rentals
110 properties allow pets
Rentals with a pool
20 properties have a pool

Frequently Asked Questions

Are there pet-friendly vacation rentals in Jamaica?
Four-legged friends are welcome in Jamaica. Choose from more than 110 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 110 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 chalet rentals in Jamaica?
Experience the best of Jamaica with our chalet rentals, starting at about $90 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 wifi?
Absolutely! We offer over 130 house 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 50 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 cabin rentals in Jamaica have air conditioning?
Absolutely! We offer over 10 cabin rentals with air conditioning in Jamaica. Enjoy a tailored experience with all the comforts you desire.
Are there Jamaica house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 house rentals with pools in Jamaica, available on Airbnb. Make a splash and soak up the sun in style!
Are there family-friendly cabin rentals in Jamaica?
Jamaica has more than 20 family-friendly cabin rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Chalet Rentals in Jamaica?
Enhance your stay in our Chalet Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with a bbq area, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore