Jamaica Holiday Rentals

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Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

Our top choices for Jamaica holiday rentals

Smart TV, fireplace, books, stereo

Hot Tub Sauna EV Sleeps 10 | Stratton A-Frame Escape

Hot Tub Sauna EV Sleeps 10 | Stratton A-Frame Escape
Jamaica
10.0 out of 10, Exceptional, (3 reviews)
"Great peaceful stay. Hosts were always in communication with us. Close to Stratton. Hot tube & sauna were a great top off to a day of skiing. "
United States
fran g.
The price is HK$2,410
HK$6,566 total
includes taxes & fees
30 Mar - 31 Mar
Hot Tub Sauna EV Sleeps 10 | Stratton A-Frame Escape
Exterior

Family-friendly A-Frame near Stratton, Bromley & Magic — hot tub retreat in the quiet, peaceful woods

Family-friendly A-Frame near Stratton, Bromley & Magic — hot tub retreat in the quiet, peaceful woods
Jamaica
8.8 out of 10, Excellent, (8 reviews)
"Great location. House was recently updated but has some older charm in parts. Fun and cozy. Hot tub was great the first day but smell seemed off the next day. Perhaps more chlorine was needed. Great time , great trip. Pet friendly is a bonus and the house looks never used so the cleaning crew is doing great work. Will rent again next year perhaps !"
United States
Michael C.
The price is HK$2,585
HK$5,653 total
includes taxes & fees
30 Mar - 31 Mar
Family-friendly A-Frame near Stratton, Bromley & Magic — hot tub retreat in the quiet, peaceful woods
Exterior

Wellness Getaway with a Personal Sauna, and Private River Beach!

Wellness Getaway with a Personal Sauna, and Private River Beach!
Newfane
10.0 out of 10, Exceptional, (3 reviews)
"Very welcoming and extremely helpful. Had a wonderful stay post ski day! Would definitely recommend and stay again. "
United States
Joseph P.
The price is HK$1,057
HK$2,009 total
includes taxes & fees
2 Apr - 3 Apr
Wellness Getaway with a Personal Sauna, and Private River Beach!
Interior

Outdoor Adventure Hub! Family Home in West Dover

Outdoor Adventure Hub! Family Home in West Dover
3.0 star property
West Dover
The price is HK$1,198
HK$4,085 total
includes taxes & fees
30 Mar - 31 Mar
Outdoor Adventure Hub! Family Home in West Dover
TV, books

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Walpole
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
The price is HK$1,525
HK$1,875 total
includes taxes & fees
29 Mar - 30 Mar
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Outdoor pool, a heated pool

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Perfect spot for Mount Snow "
United States
Bobby
The price is HK$480
HK$2,489 total
includes taxes & fees
29 Mar - 30 Mar
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Property grounds

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (59 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is HK$1,292
HK$2,412 total
includes taxes & fees
29 Mar - 30 Mar
Family Friendly Hilltop House In Putney Vermont
Exterior

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (168 reviews)
"Very nice and clean cabin, not too far from small towns, decently supplied for expected conveniences, charming area - a small stream nearby provides a pleasant background noise. "
United States
Philip
The price is HK$1,330
HK$2,717 total
includes taxes & fees
8 Apr - 9 Apr
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Interior

Cozy cabin in charming Londonderry

Cozy cabin in charming Londonderry
Londonderry
8.4 out of 10, Very good, (5 reviews)
"Very cozy and quiet. "
United States
Eric H.
The price is HK$1,092
HK$2,171 total
includes taxes & fees
20 Apr - 21 Apr
Cozy cabin in charming Londonderry
Private kitchen

The Studio with a View. Bring your dog, too!

The Studio with a View. Bring your dog, too!
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"Great cozy little mountain cabin stay!! Well-appointed studio barn/cabin with scenic view and great proximity to skiing. Would stay again : )"
United States
James M.
The price is HK$1,033
HK$2,068 total
includes taxes & fees
8 Apr - 9 Apr
The Studio with a View. Bring your dog, too!
Children’s area

Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.4 out of 10, Exceptional, (10 reviews)
"Great location, steps to the Plaza trail, clean and well stocked with kitchen gear, towels etc. The furniture is a little dated but overall a great place to stay! Loved it!"
United States
Barb C.
The price is HK$709
HK$2,553 total
includes taxes & fees
30 Mar - 31 Mar
Cozy Bromley Retreat
Interior

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
7.6 out of 10, Good, (56 reviews)
"Irish Bar nearby was a plus on St. Patrick’s Day !"
United States
Warren
The price is HK$446
HK$2,335 total
includes taxes & fees
8 Apr - 9 Apr
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Terrace/patio

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Walpole
10.0 out of 10, Exceptional, (51 reviews)
"We had a very lovely stay. "
United States
mary c.
The price is HK$2,254
HK$4,653 total
includes taxes & fees
30 Mar - 31 Mar
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Interior

Outdoor Adventure Haven 14 Mi to Mount Snow Skiing

Outdoor Adventure Haven 14 Mi to Mount Snow Skiing
3.0 star property
Newfane
The price is HK$1,761
HK$4,502 total
includes taxes & fees
29 Mar - 30 Mar
Outdoor Adventure Haven 14 Mi to Mount Snow Skiing
Dining

Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes
Chester Depot
9.6 out of 10, Exceptional, (18 reviews)
"House was in a perfect location. The town was adorable. "
United States
Michelle A.
The price is HK$1,628
HK$3,330 total
includes taxes & fees
29 Mar - 30 Mar
Charming Chester Farmhouse near Near VT Slopes
Property grounds

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Clock Tower Base Area
9.0 out of 10, Wonderful, (78 reviews)
"Unit was as advertised. Clean and comfortable."
United States
Ralph D.
The price is HK$618
HK$2,068 total
includes taxes & fees
8 Apr - 9 Apr
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Living area

Cozy Private Cabin in Andover - Fireplace & Hot tub

Cozy Private Cabin in Andover - Fireplace & Hot tub
Andover
The price is HK$1,713
HK$3,873 total
includes taxes & fees
8 Apr - 9 Apr
Cozy Private Cabin in Andover - Fireplace & Hot tub
Outdoor dining

Ski-in/out mountainside condo with balcony, washer/dryer & high-speed WiFi

Ski-in/out mountainside condo with balcony, washer/dryer & high-speed WiFi
Clock Tower Base Area
8.6 out of 10, Excellent, (14 reviews)
"Great stay at Okemo. Super convenient to get to the lifts and unit was well maintained. Couldn’t find pillow cases for the pull out couch but otherwise everything was well appointed. Check in/check out was super easy. Thank you!"
United States
Kristin S.
The price is HK$822
HK$2,365 total
includes taxes & fees
31 Mar - 1 Apr
Ski-in/out mountainside condo with balcony, washer/dryer & high-speed WiFi
Interior

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Cozy little spot that had everything we needed. Peaceful, quiet, and once the rain let up on our stay we walked out to the gorgeous little pond on the property. So serene. Catherine was great!"
United States
Erica H.
The price is HK$666
HK$1,611 total
includes taxes & fees
31 Mar - 1 Apr
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Interior

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Stratton
7.8 out of 10, Good, (56 reviews)
"Location was great, pool, hot tubs and sauna were great"
United States
Lin M.
The price is HK$689
HK$2,108 total
includes taxes & fees
21 Apr - 22 Apr
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Jamaica Hotel Reviews

Valley Craft Ales

Valley Craft Ales

10/10 Excellent
"Great place for a one night stay to ski near by. Clean room and great pizza in the brewery. "
Laura 1-night trip
Posted 4 hours ago
Valley Craft Ales

Find out more about Jamaica

Search for holiday rentals in Jamaica on Expedia! You can easily find your home rentals, villas, holiday apartments in Jamaica using one of the methods below:

  • View our selection of featured holiday rentals in Jamaica
  • Use the map to find apartments and other holiday homes in the Jamaica neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Jamaica while they last

Look no further and take a look at our great range of rental properties in Jamaica!

Frequently asked questions

Can I find holiday rentals in Jamaica?

Yes, there are holiday rentals close to the most popular sights in Jamaica, or you can select a more secluded option if you're looking for a relaxing stay. Jamaica is known for its mountain views and art. Make sure you have time to check out the monuments while you're in the area.

What are some of the best holiday rentals that Jamaica has to offer?

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms: This holiday home rental outside of Jamaica is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 12 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Jamaica?

With 43 Expedia holiday rentals, you're guaranteed to find just the right place for your Jamaica stay.

What can I see and do in Jamaica?

Cultural attractions include Hot Glass Works and Margie's Muse Handweaving & Gallery, whereas Green Mountain National Forest and Winhall River are a couple of picturesque spots to enjoy the outdoors. Jamaica State Park and Ball Mountain State Park are other places to visit while you're in town.

What are holiday rentals like in Jamaica?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Jamaica. Holiday rentals offer extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for family gatherings.