A road flanked by dense bamboo groves.

Holiday Rentals in Jamaica

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Jamaica holiday rentals

A rustic cabin with a hammock, wicker chairs, and a wooden deck surrounded by autumn foliage.

1. Cabin-Swim-Brook View-Woodfired Sauna-Firepit-Woodstove-7 min to Stratton-Dog OK

Cabin-Swim-Brook View-Woodfired Sauna-Firepit-Woodstove-7 min to Stratton-Dog OK
JAMAICA
10.0 out of 10, Exceptional, (1 review)
"Had a great couple days at the "glamping cabin." The ride to get there on a dark foggy night was a bit thrilling, but could immediately relax once I got into the cabin. Place has everything needed for a semi-primitive cabin experience. Enjoyed the sauna and thencozy bed. "
United States
Brittney C.
Cabin-Swim-Brook View-Woodfired Sauna-Firepit-Woodstove-7 min to Stratton-Dog OK
A spacious living room with a high ceiling, wooden beams, a large sofa, a dining table, and a view of the outdoors through large windows.

2. 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 €776
includes taxes & fees
29 Sept - 30 Sept
Vermont A-Frame | Sleeps10, Hot Tub, Sauna, EV, AC
A lodge with a large fireplace, a covered porch, and a staircase leading to the upper level.

3. 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 €492
includes taxes & fees
27 Sept - 28 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.

4. 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 €965
includes taxes & fees
29 Sept - 30 Sept
Cozy A-Frame Cabin with Hot Tub & Sauna near Stratton Mountain, Vermont
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

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 €232
includes taxes & fees
29 Sept - 30 Sept
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
A building with a sign reading 'Fire Tower Restaurant & Tavern.'

6. 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 €203
includes taxes & fees
28 Sept - 29 Sept
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
A spacious living room with a stone fireplace, wooden beams, and a large sofa.

7. 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 €523
includes taxes & fees
28 Sept - 29 Sept
Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
A rectangular pool with a brick deck, surrounded by lounge chairs and umbrellas.

8. 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 €275
includes taxes & fees
27 Sept - 28 Sept
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
A modern kitchen with dark cabinetry, stainless steel appliances, and a bar area with stools.

9. 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, (35 reviews)
"Great space, great location!"
United States
Jason S.
The price is €413
includes taxes & fees
27 Sept - 28 Sept
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
A swimming pool with a stone border, surrounded by a snow-covered landscape and a wooden fence.

10. 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, (84 reviews)
"Nice place and great location!!!"
United States
William
The price is €387
includes taxes & fees
27 Sept - 28 Sept
Long Trail House at Stratton Mountain Resort
A wooden deck with a black Adirondack chair and a small table, surrounded by trees.

11. 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 €391
includes taxes & fees
28 Sept - 29 Sept
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
A living room with a sofa, a television, a fireplace, and a dining area with chairs and a table.

12. 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 €284
includes taxes & fees
27 Sept - 28 Sept
Lovely ski-in/out condo steps from ski lift with trails and amazing views
A multi-story building with a stone facade, a central courtyard with a hot tub, and a stone pathway.

13. 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 €365
includes taxes & fees
27 Sept - 28 Sept
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
A living room with a television, sofa, and coffee table.

14. Long Trail House South Wing 2B2B Condo

Long Trail House South Wing 2B2B Condo
Stratton
10.0 out of 10, Exceptional, (5 reviews)
The price is €438
includes taxes & fees
4 Oct - 5 Oct
Long Trail House South Wing 2B2B Condo
A cozy room with wooden walls, two green upholstered chairs with plaid cushions, a small round wooden table with a cup and a book, and a framed map of Vermont on the wall.

15. 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 €741
includes taxes & fees
21 Oct - 22 Oct
The MountainTop | Stratton & Mt Snow | Fire Pit
A calm lake with a wooden boat on the shore.

16. 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 €269
includes taxes & fees
5 Oct - 6 Oct
Cozy 3 bedroom condo 2.5 miles to Mount Snow
A red house with a covered porch and a chimney.

17. 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 €325
includes taxes & fees
30 Sept - 1 Oct
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
A hallway with a bench, a wall-mounted towel rack, and a door leading to an outdoor area.

18. 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 €420
includes taxes & fees
29 Sept - 30 Sept
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
A spacious kitchen with a large island, a stone fireplace, and wooden beams.

19. Views for Days | Hot Tub, Sauna, EV, A/C | 6 Min to Stratton, 15 to Bromley

Views for Days | Hot Tub, Sauna, EV, A/C | 6 Min to Stratton, 15 to Bromley
Winhall
10.0 out of 10, Exceptional, (13 reviews)
"House was great for our family ski trip! "
United States
Brooke S.
The price is €613
includes taxes & fees
1 Oct - 2 Oct
Views for Days | Hot Tub, Sauna, EV, A/C | 6 Min to Stratton, 15 to Bromley
A wooden cabin with a patio area featuring Adirondack chairs, a hot tub, and a fire pit.

20. 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.
Luxe Chalet - Leaf Peeping, Near Mt Snow and Stratton Mountain w/Hot Tub, Sauna
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
"Very nice staff, clean room and good breakfast."
Deborah 1-night trip
Posted 11 hours ago
Hampton Inn and Suites Manchester

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 45 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.