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

4.82 out of 5 average rating, 461 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.

May 8 – 15

$95 per night
Guest favorite

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!

Oct 4 – 11

$91 per night
Guest favorite

Cabin in Jamaica

4.99 out of 5 average rating, 180 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 1 – 8

$135 per night

Popular amenities for Jamaica vacation rentals

Stay near Jamaica's top sights

Winhall Brook Campground4 locals recommend
Honeypie122 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

Guest favorite

Cabin in Jamaica

4.89 out of 5 average rating, 132 reviews

Jamaica Mod A Frame

Aug 12 – 19

$252 per night
Guest favorite

Tiny home in Wilmington

4.98 out of 5 average rating, 128 reviews

Beautiful Timber Frame Retreat

Sep 4 – 11

$183 per night
Guest favorite

Guest suite in Brattleboro

4.94 out of 5 average rating, 515 reviews

Charming studio in renovated 19th century church.

Oct 17 – 24

$81 per night
Guest favorite

Apartment in Jamaica

4.98 out of 5 average rating, 107 reviews

West Wing at Mantana Meadows on the West River

May 10 – 17

$152 per night
Guest favorite

Apartment in Townshend

4.94 out of 5 average rating, 200 reviews

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

May 3 – 10

$131 per night
Guest favorite

Cottage in Newfane

4.89 out of 5 average rating, 212 reviews

Ridgeview: Cozy Cottage with a View

Oct 29 – Nov 5

$121 per night
Guest favorite

Cottage in Dover

4.95 out of 5 average rating, 216 reviews

Cozy summer cottage in the woods of southern VT

Jun 14 – 21

$103 per night
Guest favorite

Guesthouse in Brattleboro

4.93 out of 5 average rating, 421 reviews

Mahalo Temple Retreat

May 5 – 12

$79 per night
Guest favorite

Apartment in Newfane

4.97 out of 5 average rating, 397 reviews

Rock River Retreat: Pets Welcome

May 30 – Jun 6

$117 per night
Guest favorite

Tiny home in Dover

4.99 out of 5 average rating, 149 reviews

Rustic Cabin in foothills of Green Mountains

Sep 28 – Oct 5

$100 per night
Guest favorite

Chalet in Dover

4.93 out of 5 average rating, 260 reviews

A charming VT chalet

Jan 10 – 17

$147 per night
Guest favorite

Home in Winhall

4.99 out of 5 average rating, 345 reviews

Stunning mid-century house on 2.5 private acres

Aug 14 – 21

$269 per night

Other great vacation rentals in Jamaica

Guest favorite

Guesthouse in Pawlet

4.91 out of 5 average rating, 282 reviews

Picturesque Cabin on the Mettowee

Oct 31 – Nov 7

$105 per night
Guest favorite

Loft in Jamaica

4.98 out of 5 average rating, 93 reviews

Cozy Loft for your Southern VT Adventures

Jun 9 – 16

$77 per night
Guest favorite

Home in Jamaica

5.0 out of 5 average rating, 25 reviews

2-Bedroom Home, 7 Minutes From Stratton Mountain

Sep 30 – Oct 7

$135 per night
Guest favorite

Condo in Londonderry

4.95 out of 5 average rating, 42 reviews

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

Aug 29 – Sep 5

$95 per night
Guest favorite

Home in Jamaica

5.0 out of 5 average rating, 98 reviews

Stratton Spa House with Man Cave

Jun 3 – 10

$466 per night
Guest favorite

Home in Jamaica

4.83 out of 5 average rating, 76 reviews

Convenient Mt Snow/Stratton 4 Bedroom w/Balcony

May 18 – 25

$98 per night
Guest favorite

Home in Dover

4.93 out of 5 average rating, 67 reviews

Cozy Riverfront Home, 1mi to Mt Snow, On Moover

May 10 – 17

$72 per night
Guest favorite

Condo in Stratton

4.91 out of 5 average rating, 44 reviews

Stratton Mountain vacation spot

Jun 8 – 15

$78 per night
Superhost

Cabin in Jamaica

4.9 out of 5 average rating, 67 reviews

Ski Stratton 7min: Starry Sky+DogOK+HikePikesFalls

Jun 13 – 20

$118 per night
Guest favorite

Home in Windham

4.95 out of 5 average rating, 76 reviews

Artistic Southern Vt Countryside Home at Windham

May 18 – 25

$155 per night
Guest favorite

Cabin in Jamaica

4.85 out of 5 average rating, 40 reviews

Cozy Mountain Getaway

Sep 11 – 18

$138 per night
Superhost

Home in Jamaica

4.87 out of 5 average rating, 69 reviews

Coffee Lover's Retreat w/ hot tub & game room

Jul 24 – 31

$388 per night

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 chalet rentals in Jamaica have wifi?

    Absolutely! We offer over 20 chalet 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 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 chalet rentals in Jamaica?

    Jamaica has more than 20 family-friendly chalet rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for Cabin Rentals in Jamaica?

    Enhance your stay in our Cabin Rentals with the most popular amenities: over 50 homes with a bbq area, over 30 homes with wifi, over 10 homes with air conditioning, 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