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Jamaica Holiday Rentals

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Check prices for these dates

In two weeks
23 Jan - 25 Jan
In two months
6 Mar - 8 Mar
In three months
3 Apr - 5 Apr
In four months
1 May - 3 May

Our top choices for Jamaica holiday rentals

Exterior
Chalet-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK

Chalet-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK

Chalet-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK
2.0 star property
Jamaica
6.0 out of 10, (1 review)
The price is HK$818
HK$1,656 total
includes taxes & fees
19 Jan - 20 Jan
Chalet-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK
Smart TV, fireplace, books, stereo
Stratton A-Frame: Boot Warmers EV Hot Tub Sauna,1 Gbps, Manchester Okemo MT Snow

Stratton A-Frame: Boot Warmers EV Hot Tub Sauna,1 Gbps, Manchester Okemo MT Snow

Stratton A-Frame: Boot Warmers EV Hot Tub Sauna,1 Gbps, Manchester Okemo MT Snow
Jamaica
10.0 out of 10, Exceptional, (1 review)
"Couldn't be better! Outstanding! We had our family holiday ski trip from Dec 25-29th,2025. The amenities were second to none. The hot tub, sauna and fire pit made the winter warm! The house was clean comfortable and very cozy. The kitchen was extremely well appointed (sharp knives!). The staples available (coffee, tea, oil, spices etc.) were high quality and the best I've ever experienced in a short term rental. The beds and bedding were very comfortable! Most immortality the hosts were very...
United States
Laird N.
The price is HK$4,186
HK$5,364 total
includes taxes & fees
13 Jan - 14 Jan
Stratton A-Frame: Boot Warmers EV Hot Tub Sauna,1 Gbps, Manchester Okemo MT Snow
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

Family-friendly A-Frame near Stratton, Bromley & Magic — hot tub retreat in the quiet, peaceful woods
Jamaica
9.0 out of 10, Wonderful, (6 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$2,627
HK$5,720 total
includes taxes & fees
13 Jan - 14 Jan
Family-friendly A-Frame near Stratton, Bromley & Magic — hot tub retreat in the quiet, peaceful woods
Property grounds
Cottage-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK

Cottage-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK

Cottage-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK
2.0 star property
Jamaica
10.0 out of 10, Exceptional, (2 reviews)
"The cottage was great and the hosts very communicative and checking in to make sure we were all set. We will be hopefully making this a yearly trip as we loved the seclusion and beautiful area. "
United States
Kyle M.
The price is HK$1,052
HK$1,947 total
includes taxes & fees
15 Jan - 16 Jan
Cottage-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK
Exterior
Wellness Getaway with a Personal Sauna, and Private River Beach!

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

Wellness Getaway with a Personal Sauna, and Private River Beach!
2.0 star property
Newfane
10.0 out of 10, Exceptional, (2 reviews)
"The folks are SUPER and made me feel very welome"
United States
Mark
The price is HK$1,052
HK$1,929 total
includes taxes & fees
14 Jan - 15 Jan
Wellness Getaway with a Personal Sauna, and Private River Beach!
Private kitchen
The Studio with a View. Bring your dog, too!

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

The Studio with a View. Bring your dog, too!
2.0 star property
Brattleboro
10.0 out of 10, Exceptional, (1 review)
"The perfect and cozy crash pad for a weekend ski trip! The Studio made us forget about the 9 degree weather outside and had all we needed. Would recommend to anyone looking for a relaxing Vermont getaway and would stay again in a heartbeat!"
United States
Michael A.
The price is HK$779
HK$1,789 total
includes taxes & fees
11 Jan - 12 Jan
The Studio with a View. Bring your dog, too!
Property grounds
Lake Whitingham & Mount Snow Area Village Apartment

Lake Whitingham & Mount Snow Area Village Apartment

Lake Whitingham & Mount Snow Area Village Apartment
2.0 star property
Whitingham
10.0 out of 10, Exceptional, (1 review)
"This place was cozy and romantic, making it the perfect escape from the hustle and bustle of city life. The location is ideal, with charming New England towns to explore in every direction. Amy and Connor were exceptional hosts, checking in with us throughout our stay to ensure we felt right at home."
United States
Anicia K.
The price is HK$1,091
HK$2,382 total
includes taxes & fees
11 Jan - 12 Jan
Lake Whitingham & Mount Snow Area Village Apartment
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

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.2 out of 10, Wonderful, (18 reviews)
"So cute and in such a great area! It was a perfect stay"
United States
Jaden F.
The price is HK$345
HK$2,293 total
includes taxes & fees
3 Feb - 4 Feb
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Exterior
Mountain Chalet mins from Mt Snow Skiing/hiking

Mountain Chalet mins from Mt Snow Skiing/hiking

Mountain Chalet mins from Mt Snow Skiing/hiking
East Dover
9.8 out of 10, Exceptional, (10 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is HK$730
HK$3,166 total
includes taxes & fees
12 Jan - 13 Jan
Mountain Chalet mins from Mt Snow Skiing/hiking
Children’s area
Cozy Bromley Retreat

Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.4 out of 10, Exceptional, (10 reviews)
"As always, an excellent stay. Wonderful unit, very nicely stocked in a perfect location. Communication was quick and easy. Easily my favorite place to stay!"
United States
Vanessa P.
The price is HK$723
HK$2,544 total
includes taxes & fees
13 Jan - 14 Jan
Cozy Bromley Retreat
Interior
Beautiful country cabin with hot tub and outdoor shower in Londonderry

Beautiful country cabin with hot tub and outdoor shower in Londonderry

Beautiful country cabin with hot tub and outdoor shower in Londonderry
2.0 star property
Londonderry
10.0 out of 10, Exceptional, (2 reviews)
"On a farm in the country…..stars blazing at night for hot tub. Cozy loft had amazing mattress and pillows! Our dog enjoyed the surrounding field. Beautiful! "
United States
Laurel
The price is HK$1,157
HK$2,857 total
includes taxes & fees
14 Jan - 15 Jan
Beautiful country cabin with hot tub and outdoor shower in Londonderry
Exterior
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

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, (166 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$1,325
HK$2,880 total
includes taxes & fees
21 Jan - 22 Jan
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Interior
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

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, (53 reviews)
"Irish Bar nearby was a plus on St. Patrick’s Day !"
United States
Warren
The price is HK$616
HK$2,829 total
includes taxes & fees
14 Jan - 15 Jan
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Lobby
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Dover
8.8 out of 10, Excellent, (32 reviews)
"Very nice accommodations and location!"
United States
Michael M.
The price is HK$826
HK$3,041 total
includes taxes & fees
1 Feb - 2 Feb
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
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

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Clock Tower Base Area
9.0 out of 10, Wonderful, (75 reviews)
"Perfect location for a quick ski trip. "
United States
Michael D.
The price is HK$967
HK$2,753 total
includes taxes & fees
14 Jan - 15 Jan
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Beach
Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow
West Dover
9.0 out of 10, Wonderful, (46 reviews)
"Great quiet location, kitchen had enough essentials for basic cooking to be easy. The king bed was comfortable and the living room is a great hangout spot."
United States
Franklin C.
The price is HK$779
HK$2,404 total
includes taxes & fees
10 Feb - 11 Feb
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Outdoor spa tub
Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort
3.0 star property
Stratton
8.4 out of 10, Very good, (78 reviews)
"The building and the units are old and tired. Early attic decorating. And the walls are paper thin. We could hear all neighbors. I would not go back. "
United States
Doug
The price is HK$3,030
HK$3,767 total
includes taxes & fees
12 Jan - 13 Jan
Long Trail House at Stratton Mountain Resort
TV, fireplace, books, stereo
Secluded Vermont Chalet w/ Sweeping Mountain Views

Secluded Vermont Chalet w/ Sweeping Mountain Views

Secluded Vermont Chalet w/ Sweeping Mountain Views
2.0 star property
Dover
The price is HK$1,060
HK$3,961 total
includes taxes & fees
12 Jan - 13 Jan
Secluded Vermont Chalet w/ Sweeping Mountain Views
Exterior
Romantic Riverbed Treehouse - hot tub & new sauna!

Romantic Riverbed Treehouse - hot tub & new sauna!

Romantic Riverbed Treehouse - hot tub & new sauna!
londonderry
9.4 out of 10, Exceptional, (3 reviews)
"We had a great stay. Place was very romantic with great views. Host was responsive."
United States
Brian G.
The price is HK$1,466
HK$5,048 total
includes taxes & fees
12 Jan - 13 Jan
Romantic Riverbed Treehouse - hot tub & new sauna!
Interior
Cozy cabin in charming Londonderry

Cozy cabin in charming Londonderry

Cozy cabin in charming Londonderry
Londonderry
9.4 out of 10, Exceptional, (3 reviews)
"Very cozy and quiet. "
United States
Eric H.
The price is HK$1,087
HK$2,162 total
includes taxes & fees
12 Jan - 13 Jan
Cozy cabin in charming Londonderry
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

The White House Inn

The White House Inn

10/10 Excellent
"This is the second year we stay at the White House Inn while we ski at Mount Snow. We love the spacious clean room. Nice amenities and a wonderful large shower. I'm not fond of a puffy mattress, but it still was comfortable. We enjoyed the breakfast, plenty of fruit, fresh baked coffee cake and pastries, varieties of toast, muffins, cereals, yogurt, oatmeal. We had a wonderful dinner in Clara's Cucina Restaurant. A true elegant dinning experience. We will return next year."
Roberta 2-night trip
Posted 2 days ago
The White House Inn

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?

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns: This holiday home rental outside of Jamaica is located on a river, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 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 balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Jamaica?

With 40 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 Winhall River and Green Mountain National Forest are a couple of picturesque spots to enjoy the outdoors. You’ll find favourite places to visit such as Stratton Mountain Resort and Mount Snow in the wider area.

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.