Holiday rentals in Jamaica

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Jamaica

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

Guest favourite
Tiny home in Jamaica
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.
15–22 Apr
$104 SGD per night
4.89 out of 5 average rating, 343 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
$121 SGD per night
4.93 out of 5 average rating, 308 reviews
Guest favourite
Cabin in Jamaica
Jamaica Mod A Frame
Set above where the Wardsboro brook meets the West River in Jamaica, VT, our completely renovated A-frame blends the best of nature and modern living for a perfect getaway experience. Close to Stratton, Mt. Snow, Magic Mountain & Bromley as well as Ball Mountain Brook, Jamaica State Park, Hamilton and Pikes Falls. Put on some records and cozy up to the fire, listen to the river soaking in our wood burning hot tub or roast some marshmallows and check out the stars-this is the recharge you need.
2–9 Jun
$319 SGD per night
4.89 out of 5 average rating, 132 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

Guest favourite
Barn in Marlboro
The Studio With a View. Bring your dog, too!
24–31 Jan
$163 SGD per night
4.95 out of 5 average rating, 260 reviews
Guest favourite
Home in Jamaica
2-Bedroom Home, 7 Minutes From Stratton Mountain
18–25 Apr
$168 SGD per night
5.0 out of 5 average rating, 25 reviews
Guest favourite
Loft in Jamaica
Cozy Loft for your Southern VT Adventures
1–8 May
$109 SGD per night
4.98 out of 5 average rating, 93 reviews
Superhost
Home in Jamaica
Coffee Lover's Retreat w/ hot tub & game room
24–31 Jul
$519 SGD per night
4.87 out of 5 average rating, 69 reviews
Guest favourite
Cabin in Jamaica
Wishing Well Cabin
4–11 Nov
$321 SGD per night
5.0 out of 5 average rating, 31 reviews
Guest favourite
Home in Jamaica
Stratton Mountain Escape With Views
3–10 Sep
$426 SGD per night
4.96 out of 5 average rating, 27 reviews
Guest favourite
Home in Windham
Artistic Southern Vt Countryside Home at Windham
4–11 May
$199 SGD per night
4.95 out of 5 average rating, 76 reviews
Guest favourite
Chalet in Jamaica
Tall Pines Mountain Home near Stratton & Mt Snow
6–13 Aug
$478 SGD per night
5.0 out of 5 average rating, 30 reviews
Guest favourite
Home in Jamaica
Magic Cottage in Jamaica Vermont
8–15 Sep
$300 SGD per night
5.0 out of 5 average rating, 8 reviews
Superhost
Cabin in Jamaica
Ski Stratton 7min: Starry Sky+DogOK+HikePikesFalls
8–15 Jun
$156 SGD per night
4.89 out of 5 average rating, 66 reviews
Guest favourite
Cabin in Jamaica
Near Stratton! Cozy + Rustic w Fireplace + Firepit
27 Mar – 3 Apr
$388 SGD per night
5.0 out of 5 average rating, 37 reviews
Guest favourite
Apartment in Londonderry
Magical Ski-In/Ski-Out Condo at Magic w/ game room
21–28 Aug
$129 SGD per night
4.95 out of 5 average rating, 41 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

$27 SGD before taxes and fees

Destinations to explore

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