A road flanked by dense bamboo groves.

Jamaica Holiday Rentals

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Jamaica holiday rentals

Smart TV, fireplace, books, stereo

1. Vermont A-Frame | Sleeps10, Hot Tub, Sauna, EV, AC

Vermont A-Frame | Sleeps10, Hot Tub, Sauna, EV, AC
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$1,876
HK$6,970 total
includes taxes & fees
24 Sept - 25 Sept
Vermont A-Frame | Sleeps10, Hot Tub, Sauna, EV, AC
Exterior

2. Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.

Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.
Jamaica
8.8 out of 10, Excellent, (8 reviews)
"Beautiful home, we enjoyed our stay!"
United States
Luke B.
The price is HK$3,256
HK$4,806 total
includes taxes & fees
21 Sept - 22 Sept
Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.
Exterior

3. Cozy A-Frame Cabin with Hot Tub & Sauna near Stratton Mountain, Vermont

Cozy A-Frame Cabin with Hot Tub & Sauna near Stratton Mountain, Vermont
Jamaica
The price is HK$6,470
HK$8,357 total
includes taxes & fees
28 Sept - 29 Sept
Cozy A-Frame Cabin with Hot Tub & Sauna near Stratton Mountain, Vermont
Exterior

4. Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna

Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
Stratton
The price is HK$585
HK$1,761 total
includes taxes & fees
20 Sept - 21 Sept
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
Interior

5. 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
The price is HK$585
HK$2,009 total
includes taxes & fees
23 Sept - 24 Sept
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
TV, fireplace

6. Lovely ski-in/out condo steps from ski lift with trails and amazing views

Lovely ski-in/out condo steps from ski lift with trails and amazing views
Stratton
8.4 out of 10, Very good, (36 reviews)
"I have stayed in this condo a few times now, and for my needs it is a great value; affordable, comfortable and ideal location. "
United States
eric m.
The price is HK$585
HK$2,461 total
includes taxes & fees
20 Sept - 21 Sept
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Coffee/tea maker, fridge, microwave, oven

7. Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub

Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
Stratton Mountain
10.0 out of 10, Exceptional, (34 reviews)
"Great space, great location!"
United States
Jason S.
The price is HK$1,236
HK$3,462 total
includes taxes & fees
21 Sept - 22 Sept
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
Outdoor spa tub

8. Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort
3.0 star property
Stratton
8.6 out of 10, Excellent, (83 reviews)
"Nice place and great location!!!"
United States
William
The price is HK$2,785
HK$3,462 total
includes taxes & fees
27 Sept - 28 Sept
Long Trail House at Stratton Mountain Resort
Outdoor pool, a heated pool

9. 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)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
The price is HK$381
HK$2,355 total
includes taxes & fees
20 Sept - 21 Sept
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Terrace/patio

10. Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Wardsboro
10.0 out of 10, Exceptional, (20 reviews)
"Cute place, very pet-friendly."
United States
Jeff H.
The price is HK$1,452
HK$3,493 total
includes taxes & fees
22 Sept - 23 Sept
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Property grounds

11. Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Stratton
8.0 out of 10, Very good, (1 review)
The price is HK$1,096
HK$3,179 total
includes taxes & fees
22 Sept - 23 Sept
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Interior

12. Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester

Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
Londonderry
9.6 out of 10, Exceptional, (24 reviews)
"Super attentive and accommodating host! It was a perfect cozy getaway on a frigid weekend, and the fireplace and hot tub were just the ticket. "
United States
Meghan R.
The price is HK$1,644
HK$4,659 total
includes taxes & fees
21 Sept - 22 Sept
Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
Interior

13. The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!

The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
Wardsboro
10.0 out of 10, Exceptional, (11 reviews)
"Loved this place so much! Adorable spot, quaint but has everything you need. Loved the luxury details. "
United States
Carly L.
The price is HK$1,648
HK$4,123 total
includes taxes & fees
18 Oct - 19 Oct
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
Coffee/tea maker, fridge, microwave, oven

14. The MountainTop | Stratton & Mt Snow | Fire Pit

The MountainTop | Stratton & Mt Snow | Fire Pit
Stratton
10.0 out of 10, Exceptional, (10 reviews)
"Lovely place to stay. The stars truly are stunning. "
United States
Brenna G.
The price is HK$1,899
HK$4,521 total
includes taxes & fees
21 Sept - 22 Sept
The MountainTop | Stratton & Mt Snow | Fire Pit
Smart TV

15. Long Trail House South Wing 2B2B Condo

Long Trail House South Wing 2B2B Condo
Stratton
10.0 out of 10, Exceptional, (4 reviews)
"Great location. Very clean accomodations with comfortable beds! Host was very communicative as well!"
United States
carlene p.
The price is HK$1,624
HK$3,838 total
includes taxes & fees
30 Sept - 1 Oct
Long Trail House South Wing 2B2B Condo
Exterior

16. 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, (172 reviews)
"We had a very lovely stay. The kitchen was well-equipped and the whole home was very cozy. There was wood for the wood stove and lots of games and puzzles to do. Check-in and check-out was simple. Just what we were looking for! "
United States
Eleanor D.
The price is HK$1,334
HK$2,838 total
includes taxes & fees
22 Sept - 23 Sept
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Beach

17. Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow
West Dover
9.2 out of 10, Wonderful, (52 reviews)
"The place was absolutely relaxing, clean, and one of the best host we’ve ever had an experience with. Will come back!!"
United States
Scott S.
The price is HK$734
HK$2,337 total
includes taxes & fees
30 Sept - 1 Oct
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Exterior

18. Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (16 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is HK$937
HK$3,478 total
includes taxes & fees
27 Sept - 28 Sept
Chalet Mount Snow/Stratton Skiing/hiking
Terrace/patio

19. Luxe Chalet - Leaf Peeping, Near Mt Snow and Stratton Mountain w/Hot Tub, Sauna

Luxe Chalet - Leaf Peeping, Near Mt Snow and Stratton Mountain w/Hot Tub, Sauna
Stratton
10.0 out of 10, Exceptional, (7 reviews)
"Everything about our stay was top notch. Highly recommend and I will book this house again. "
United States
samantha b.
The price is HK$1,914
HK$5,665 total
includes taxes & fees
20 Sept - 21 Sept
Luxe Chalet - Leaf Peeping, Near Mt Snow and Stratton Mountain w/Hot Tub, Sauna
Children’s area

20. Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.4 out of 10, Exceptional, (20 reviews)
"Nice place "
United States
Janja L.
The price is HK$1,010
HK$2,951 total
includes taxes & fees
4 Oct - 5 Oct
Cozy Bromley Retreat
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

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"Location was perfect!"
brenda 2-night trip
Posted 4 hours ago
Hampton Inn and Suites Manchester

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?

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: 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 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Jamaica?

With 46 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 West River 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.