Vacation rentals in Jamaica

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Top-rated holiday rentals in Jamaica

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

Guest favourite
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.
9 – 16 Apr
4.82 out of 5 average rating, 460 reviews
Guest favourite
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!
7 – 14 Aug
4.93 out of 5 average rating, 308 reviews
Guest favourite
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.
13 – 20 June
4.99 out of 5 average rating, 180 reviews

Popular amenities for Jamaica holiday 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 holiday rentals in Jamaica

Superhost
Home in Jamaica
Cozy Riverfront Home in beautiful Jamaica
17 – 24 Dec
4.96 out of 5 average rating, 157 reviews
Guest favourite
Apartment in Brattleboro
Contemporary forest eco-retreat, mountain views
7 – 14 June
4.96 out of 5 average rating, 145 reviews
Guest favourite
Cottage in Town of Rockingham
Peaceful Mountain Cottage
15 – 22 Apr
4.94 out of 5 average rating, 216 reviews
Guest favourite
Cottage in Newfane
Cozy Vermont Antique Sugar House with Fireplace
2 – 9 Dec
4.99 out of 5 average rating, 171 reviews
Guest favourite
Apartment in Newfane
Rock River Retreat: Pets Welcome
21 – 28 May
4.97 out of 5 average rating, 397 reviews
Guest favourite
Home in Jamaica
2-Bedroom Home, 7 Minutes From Stratton Mountain
26 Apr – 3 May
5.0 out of 5 average rating, 25 reviews
Guest favourite
Loft in Jamaica
Cozy Loft for your Southern VT Adventures
9 – 16 June
4.98 out of 5 average rating, 93 reviews
Guest favourite
Condo in Londonderry
Magical Ski-In/Ski-Out Condo at Magic w/ game room
21 – 28 Apr
4.95 out of 5 average rating, 41 reviews
Superhost
Cabin in Jamaica
Ski Stratton 7min: Starry Sky+DogOK+HikePikesFalls
25 Apr – 2 May
4.89 out of 5 average rating, 66 reviews
Guest favourite
Home in Windham
Artistic Southern Vt Countryside Home at Windham
5 – 12 May
4.95 out of 5 average rating, 76 reviews
Guest favourite
Cabin in Jamaica
Cozy Mountain Getaway
11 – 18 Sept
4.85 out of 5 average rating, 40 reviews
Guest favourite
Home in Jamaica
Stratton Spa House with Man Cave
2 – 9 May
5.0 out of 5 average rating, 98 reviews

Quick stats about holiday 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

$30 AUD before taxes and fees

Destinations to explore

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