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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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Cottage in Jamaica

4.82 out of 5 average rating, 462 reviews

Forest Cottage ~ 7min to Stratton, Private, Views

Authentic Vermont post & beam cottage with privacy. 3 miles to Stratton's Sun Bowl, a 7-minute drive. Nearby swimming hole at the brook on the property. Dogs welcome, $30 fee per dog. No cats due to allergies. Vinyl record player, VCR/DVD player, board games, Starlink Satellite Internet 20-100 mbps. Heat options: 2 gas wall furnaces & wood stove. Front porch, propane BBQ, fire pit, picnic table & spectacular views of Stratton Mountain. Back deck surrounded by woods with hammock, table & chairs.

Apr 30 – May 7

Cabin in Londonderry

4.93 out of 5 average rating, 308 reviews

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond in S Londonderry, VT. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery and hiking right outside your front door. The Cabin has an open floor plan with a galley kitchen, dining/living area with pullout futon couch & 1 full bathroom. 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!

Aug 21 – 28

Cabin in Jamaica

4.99 out of 5 average rating, 184 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.

Sep 2 – 9

Guesthouse in Jamaica

4.95 out of 5 average rating, 133 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.

May 23 – 30

Chalet in Dover

4.93 out of 5 average rating, 264 reviews

A charming VT chalet

Charming chalet nestled in the Mt Snow valley. Relax to the sound of a babbling brook in the back yard while you hang around a stone fire pit! Unwind in the quiet serenity of this country home complete with fully equipped kitchen with a newly installed gas fireplace , a comfy open living room with flat screen cable tv & DVD player Roko & High speed Internet . We have a lock box located on the post near the front entrance. combo provided upon arrival . Washer & dryer located on first level.

Nov 30 – Dec 7

Apartment in Jamaica

4.84 out of 5 average rating, 199 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.

Oct 14 – 21

Barn in Marlboro

4.95 out of 5 average rating, 263 reviews

The Studio With a View. Bring your dog, too!

Our stylish Studio, a not so tiny Tiny House, is nestled into the Southern Vermont hillside and surrounded by nature. Enjoy the view from the deck, and cozy up in the newly renovated flower barn with a cup of coffee or tea and a great book. Well-mannered dogs are welcome, they will enjoy the fenced-in area right off the deck. Features: efficiency kitchen and dining area, cozy living space, queen-size bed, and a full bathroom. The large covered porch overlooks fields and trees.

Nov 24 – Dec 1

Barn in Chester

4.99 out of 5 average rating, 492 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.

Sep 22 – 29

Cabin in Jamaica

4.88 out of 5 average rating, 263 reviews

Green Mountain Modern House: iconic modern getaway

Our unique, contemporary home is in the heart of the Green Mountain National Forest, all while offering all the perks of modern luxury in a secluded setting. Our amenities include open concept living and dining room, sauna, wood burning fireplace, front deck, backyard with fire pit and Adirondack chairs, and contemporary design and decor throughout. Now with EV charger, on-demand backup generator and high speed Starlink wifi (200+ mbs)! Pets welcome with a $100 pet fee.

Dec 5 – 12

Tiny home in Jamaica

4.85 out of 5 average rating, 213 reviews

Hot Tub Farmhouse - Buttercup Studio - Jamaica VT.

The calendar is accurate. Hot Tub accommodates 2-3 people comfortably. This private tiny house includes fresh linens, dedicated Wi-Fi, a kitchenette, hot shower, flushing toilet, and porch. Comfortable for up to 4 people. We are committed to AirBnB's enhanced cleaning protocol. All high-touch surfaces are sanitized. We provide extra cleaning supplies for our guests to use as they desire.

Aug 2 – 9

Apartment in Andover

4.98 out of 5 average rating, 386 reviews

Private Hilltop farm apartment

Our cozy apartment is located on a beautiful hilltop farm with views out from the porch across horse pasture and to the mountains as far away as New Hampshire. There are over 100 acres of field to walk through as well as a mile long trail running down through our property. We are 15 minutes from Chester, Ludlow and Weston. We also have very fast internet!

Sep 10 – 17

Apartment in Londonderry

4.94 out of 5 average rating, 333 reviews

Cozy Suite in a Historic Building Near Ski Resorts

Located on the second floor of a historical building in the Village of South Londonderry, Vermont, this renovated studio suite features unique touches of modern amenities but with a Vermont feel. Your room will include a 65 inch Smart TV, WiFi, electric fireplace, lush queen bed, full renovated bathroom, small kitchenette, as well as on site parking.

Jul 5 – 12

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Popular amenities for Jamaica vacation rentals

Laptop-friendly workspace

Air conditioning

Stay near Jamaica's top sights

Honeypie122 locals recommend

Winhall Brook Campground4 locals recommend

Workhorse Cafe35 locals recommend

Hamilton Falls27 locals recommend

Ungrounded Coffee Roasters27 locals recommend

Fran's Kitchen & Diner18 locals recommend

Other great vacation rentals in Jamaica

Apartment in Townshend

4.94 out of 5 average rating, 203 reviews

Private Apt. on Farm, great views and Hot tub,

Dec 16 – 23

Cabin in Jamaica

4.9 out of 5 average rating, 134 reviews

Jamaica Mod A Frame

Jan 18 – 25

Tiny home in Wilmington

4.99 out of 5 average rating, 136 reviews

Beautiful Timber Frame Retreat

Sep 10 – 17

Cottage in Newfane

4.99 out of 5 average rating, 173 reviews

Cozy Vermont Antique Sugar House with Fireplace

Jan 20 – 27

Cabin in Wardsboro

4.8 out of 5 average rating, 202 reviews

Log Cabin Near Stratton/Mt Snow

Sep 7 – 14

Apartment in Brattleboro

4.96 out of 5 average rating, 149 reviews

Contemporary forest eco-retreat, mountain views

May 8 – 15

Cottage in Newfane

4.89 out of 5 average rating, 215 reviews

Ridgeview: Cozy Cottage with a View

Nov 22 – 29

Cottage in Dover

4.84 out of 5 average rating, 262 reviews

Cozy Camp in Vermont

Apr 23 – 30

Other great vacation rentals in Jamaica

Guesthouse in Springfield

4.86 out of 5 average rating, 321 reviews

Connecticut River-Cozy Cottage

Mar 6 – 13

Apartment in Manchester

4.99 out of 5 average rating, 145 reviews

Private two-bedroom suite within a two-story house

Apr 27 – May 4

Condo in Stratton

4.96 out of 5 average rating, 93 reviews

Premier Stratton Village Location - Pool & Hot Tub

May 6 – 13

Home in Jamaica

5.0 out of 5 average rating, 26 reviews

2-Bedroom Home, 7 Minutes From Stratton Mountain

Sep 2 – 9

Cabin in Jamaica

4.89 out of 5 average rating, 70 reviews

Ski Stratton 7min: Starry Sky+DogOK+HikePikesFalls

Apr 28 – May 5

Condo in Londonderry

4.95 out of 5 average rating, 43 reviews

Magical Ski-In/Ski-Out Condo at Magic w/ game room

Nov 4 – 11

Cabin in Jamaica

4.85 out of 5 average rating, 40 reviews

Cozy Mountain Getaway

Jul 14 – 21

Home in Windham

4.95 out of 5 average rating, 77 reviews

Artistic Southern Vt Countryside Home at Windham

May 21 – 28

Quick stats about vacation rentals in Jamaica

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

Frequently Asked Questions

Are there pet-friendly vacation rentals in Jamaica?
Four-legged friends are welcome in Jamaica. Choose from more than 100 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 130 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 $120 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 chalet rentals in Jamaica have a bbq area?
Absolutely! We offer over 10 chalet 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 house rentals in Jamaica have air conditioning?
Absolutely! We offer over 40 house 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 chalet rentals in Jamaica?
Jamaica has more than 10 family-friendly chalet rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Jamaica?
Enhance your stay in our House Rentals with the most popular amenities: over 110 homes with a bbq area, over 10 homes with a gym, over 40 homes with air conditioning, over 130 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore