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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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Top guest favorite
A cozy tiny cabin, constructed with wooden beams and a sloped roof, is situated among tall trees. The porch features a railing, inviting seating, and a lantern. Sunlight filters through the foliage, casting a soft glow on the forest floor covered in pine needles.
Treehouse in Brookline
4.98 out of 5 average rating, 257 reviews

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.

Guest favorite
A gently sloping field is depicted, bordered by trees with autumn foliage. A red barn and a white building are visible in the distance, set against a bright blue sky with scattered clouds. The landscape conveys a peaceful rural setting.
Home in Townshend
4.96 out of 5 average rating, 129 reviews

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.

Guest favorite
A rustic building with wooden siding is partially surrounded by a foggy landscape. An elevated deck with rocking chairs invites relaxation. The entrance features glass doors flanked by large windows, allowing natural light to illuminate the interior. Surrounding greenery creates a serene atmosphere.
Home in Putney
4.93 out of 5 average rating, 424 reviews

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.

Top guest favorite
The cabin's exterior showcases a warm wooden facade with large, strategically placed windows. A spacious screened porch extends from the building, inviting natural light and outdoor enjoyment. A stone pathway leads to the entrance, surrounded by landscaped gravel and native vegetation.
Cabin in Jamaica
4.99 out of 5 average rating, 275 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.

Top guest favorite
The cabin features a wooden exterior surrounded by lush greenery, with large windows allowing natural light to enter. A wooden deck extends from the side, leading to a cozy outdoor area and an adjacent structure, contributing to the rustic charm of the setting.
Tiny home in Dover
5 out of 5 average rating, 203 reviews

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.

Guest favorite
Home in Jamaica
4.86 out of 5 average rating, 301 reviews

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!

Guest favorite
The compact kitchen features modern appliances, including a microwave and refrigerator, paired with wooden cabinetry and a dining area. Light-colored wood flooring extends throughout, and a staircase leads to the sleeping loft above. Decor elements include framed artwork and a vase of flowers positioned on the counter.
Tiny home in Brattleboro
4.85 out of 5 average rating, 220 reviews

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.

Guest favorite
The entrance features a white door with a decorative bell and festive wreath. Adjacent to the door is a potted plant and a small snowman figure. Two white chairs are positioned on the porch, with a light dusting of snow covering the ground.
Apartment in Jamaica
4.85 out of 5 average rating, 213 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.

Guest favorite
The tiny house exterior features a charming porch with colorful railings and vibrant green doors. Tall trees surround the cottage, and a light dusting of snow covers the ground, adding to the serene atmosphere of the setting.
Tiny home in Jamaica
4.94 out of 5 average rating, 1,308 reviews

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

Top guest favorite
A cozy living area features a mixture of seating options, including a tufted sofa and a vintage-style sofa adorned with decorative cushions. Natural wood floors enhance the warmth of the space, while artwork on the walls and a circular coffee table complete the inviting atmosphere.
Barn in Chester
4.99 out of 5 average rating, 710 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. I am as close or as far away as you would like me to be with my house right next door.

Top guest favorite
The garden features raised vegetable beds surrounded by a wooden fence. In the background, the charming former church building with a pointed steeple is visible, framed by vibrant autumn foliage in shades of red and orange.
Guest suite in Brattleboro
4.95 out of 5 average rating, 609 reviews

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.

Top guest favorite
A cozy cabin is nestled in a snow-covered landscape, featuring a blue hammock hanging from the porch. Snowflakes gently fall around a dog wearing a blue coat, playing in the deep snow in front of the entrance. Wooden stools are positioned near the entrance.
Cottage in Jamaica
4.84 out of 5 average rating, 584 reviews

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

When is the best time to visit Jamaica?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ1,205ﺩ.ﺇ1,311ﺩ.ﺇ1,083ﺩ.ﺇ804ﺩ.ﺇ826ﺩ.ﺇ786ﺩ.ﺇ848ﺩ.ﺇ826ﺩ.ﺇ826ﺩ.ﺇ936ﺩ.ﺇ995ﺩ.ﺇ1,252
Avg. temp-5°C-4°C1°C8°C14°C18°C21°C20°C16°C9°C4°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!

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Windham County
  5. Jamaica