Jamaica vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Jamaica

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

Guest favorite
Cottage in Jamaica
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 9 – 16
$93 per night
4.82 out of 5 average rating, 460 reviews
Guest favorite
Cabin in Londonderry
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 7 – 14
$91 per night
4.93 out of 5 average rating, 308 reviews
Guest favorite
Cabin in Jamaica
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.
Jun 13 – 20
$116 per night
4.99 out of 5 average rating, 180 reviews

Popular amenities for Jamaica vacation rentals

Stay near Jamaica's top sights

Hamilton Falls27 locals recommend
Winhall Brook Campground4 locals recommend
Honeypie122 locals recommend
Workhorse Cafe35 locals recommend
Ungrounded Coffee Roasters27 locals recommend
Fran's Kitchen & Diner18 locals recommend

Other great vacation rentals in Jamaica

Superhost
Home in Jamaica
Cozy Riverfront Home in beautiful Jamaica
Dec 17 – 24
$248 per night
4.96 out of 5 average rating, 157 reviews
Guest favorite
Cottage in Town of Rockingham
Peaceful Mountain Cottage
Apr 15 – 22
$88 per night
4.94 out of 5 average rating, 216 reviews
Guest favorite
Apartment in Newfane
Rock River Retreat: Pets Welcome
May 21 – 28
$118 per night
4.97 out of 5 average rating, 397 reviews
Guest favorite
Cottage in Newfane
Cozy Vermont Antique Sugar House with Fireplace
Dec 2 – 9
$135 per night
4.99 out of 5 average rating, 171 reviews
Guest favorite
Apartment in Dummerston
HeART Barn Retreat
Jul 3 – 10
$77 per night
4.96 out of 5 average rating, 153 reviews
Guest favorite
Apartment in Brattleboro
Contemporary forest eco-retreat, mountain views
Jun 7 – 14
$103 per night
4.96 out of 5 average rating, 145 reviews
Guest favorite
Apartment in Townshend
Private Apt. on Farm, great views and Hot tub,
May 2 – 9
$131 per night
4.93 out of 5 average rating, 199 reviews
Guest favorite
Condo in West Dover
Comfy Condo - 2 Min Walk to Carinthia Grommet Lift
Sep 25 – Oct 2
$96 per night
4.94 out of 5 average rating, 178 reviews
Guest favorite
Cottage in Newfane
Ridgeview: Cozy Cottage with a View
Nov 12 – 19
$121 per night
4.89 out of 5 average rating, 212 reviews
Guest favorite
Home in Winhall
Modern Cabin with Hot Tub & EV Charging Station
Jul 26 – Aug 2
$357 per night
4.98 out of 5 average rating, 121 reviews
Guest favorite
Tiny home in Wilmington
Beautiful Timber Frame Retreat
Jul 22 – 29
$214 per night
4.98 out of 5 average rating, 126 reviews
Guest favorite
Cabin in Townshend
Solar Cabin at Big Picture Farm
May 14 – 21
$262 per night
4.98 out of 5 average rating, 129 reviews

Other great vacation rentals in Jamaica

Guest favorite
Home in Winhall
Stunning mid-century house on 2.5 private acres
Jul 4 – 11
$269 per night
4.99 out of 5 average rating, 345 reviews
Guest favorite
Guesthouse in Pawlet
Picturesque Cabin on the Mettowee
Jun 1 – 8
$105 per night
4.91 out of 5 average rating, 282 reviews
Superhost
Cabin in Wardsboro
Log Cabin Near Stratton/Mt Snow
Jul 18 – 25
$131 per night
4.79 out of 5 average rating, 199 reviews
Guest favorite
Home in Jamaica
2-Bedroom Home, 7 Minutes From Stratton Mountain
Apr 26 – May 3
$113 per night
5.0 out of 5 average rating, 25 reviews
Guest favorite
Loft in Jamaica
Cozy Loft for your Southern VT Adventures
Jun 9 – 16
$77 per night
4.98 out of 5 average rating, 93 reviews
Guest favorite
Condo in Londonderry
Magical Ski-In/Ski-Out Condo at Magic w/ game room
Apr 21 – 28
$80 per night
4.95 out of 5 average rating, 41 reviews
Superhost
Cabin in Jamaica
Ski Stratton 7min: Starry Sky+DogOK+HikePikesFalls
Apr 25 – May 2
$108 per night
4.89 out of 5 average rating, 66 reviews
Guest favorite
Cabin in Jamaica
Cozy Mountain Getaway
Sep 11 – 18
$138 per night
4.85 out of 5 average rating, 40 reviews
Guest favorite
Home in Windham
Artistic Southern Vt Countryside Home at Windham
May 5 – 12
$149 per night
4.95 out of 5 average rating, 76 reviews
Superhost
Home in Jamaica
Coffee Lover's Retreat w/ hot tub & game room
Jul 24 – 31
$388 per night
4.87 out of 5 average rating, 69 reviews
Guest favorite
Home in Jamaica
Stratton Spa House with Man Cave
May 2 – 9
$433 per night
5.0 out of 5 average rating, 98 reviews
Guest favorite
Home in Jamaica
Stratton Mountain Escape With Views
Sep 4 – 11
$318 per night
4.96 out of 5 average rating, 27 reviews

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

12K 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 120 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 $140 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do cabin rentals in Jamaica have wifi?

    Absolutely! We offer over 30 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 100 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.

  • 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 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 a bbq area, over 10 homes with air conditioning, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

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