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.

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Guest favourite

Tiny homes in Jamaica

4.88 out of 5 average rating, 345 reviews

Forest Cabin ~ 7min to Stratton, Cozy, Private

Authentic Vermont post and beam cabin is 3 miles from Stratton's Sun Bowl, a short 7 minute drive away. Swimming at the brook on the property. Dogs are welcome, $30 fee per dog. Sorry, no cats due to allergies. Vinyl record player & records, VHS & videos. Full kitchen. Satellite Internet/WiFi 20-100 mbps. The bathroom has a composting toilet - it is odorless and easy to use. Heat options: 2 gas wall furnaces, wood-stove & pellet stove. Front porch, picnic table, fire pit & propane BBQ grill.

May 10 – 17

$146 CAD per night

Guest favourite

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!

Nov. 5 – 12

$163 CAD per night

Guest favourite

Home in Jamaica

5.0 out of 5 average rating, 102 reviews

Stratton Spa House with Man Cave

MANAGED BY A 5 STAR TEAM WITH MULTIPLE 5 STAR HOMES Perched on a babbling brook this 4700 square ft. contemporary has all your needs covered. Smart tech, 3 fireplaces, man cave, streaming entertainment, home theater, spa suite, hot tub, sauna, pool table, darts, poker room, dueling xbox room, giant master suite, big guest suite with wood burning stove, large dining table, fully equipped kitchen, Keurig, screened porch, 3 private acres, sun deck, bbq, 1/4m walk to water falls and swimming hole.

May 9 – 16

$640 CAD per night

Guest favourite

Cabin in Jamaica

4.99 out of 5 average rating, 187 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.

Jul. 2 – 9

$242 CAD per night

Guest favourite

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.

Jun. 7 – 14

$157 CAD per night

Guest favourite

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.

Mar. 27 – Apr. 3

$212 CAD per night

Guest favourite

Barn in Marlboro

4.95 out of 5 average rating, 264 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.

Apr. 20 – 27

$228 CAD per night

Guest favourite

Barn in Chester

4.99 out of 5 average rating, 495 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.

Aug. 20 – 27

$188 CAD per night

Superhost

Cabin in Jamaica

4.88 out of 5 average rating, 264 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.

Sep. 16 – 23

$839 CAD per night

Guest favourite

Apartment in Brattleboro

4.95 out of 5 average rating, 151 reviews

Contemporary forest eco-retreat, mountain views

This is an open, light-filled one-Bdm apartment on the lower level of our hillside home, surrounded by forests, with stunning views. Your space is 719 sf + access to laundry. We are fully vaccinated, and ask the same of guests. If you think you may have Covid please tell us. We welcome all kinds of people, regardless of race, ethnicity, gender, etc. We may ask questions before accepting people who don’t have many prior reviews. We don't take pets, sorry.

Jul. 22 – 29

$186 CAD per night

Guest favourite

Tiny homes in Jamaica

4.85 out of 5 average rating, 216 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.

May 19 – 26

$204 CAD per night

Guest favourite

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. 30 – Oct. 7

$174 CAD per night