A road flanked by dense bamboo groves.

Jamaica Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Jamaica holiday rentals

Room

1. 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$6,843
HK$8,805 total
includes taxes & fees
3 Nov - 4 Nov
Cozy A-Frame Cabin with Hot Tub & Sauna near Stratton Mountain, Vermont
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 HK$2,670
HK$8,000 total
includes taxes & fees
3 Nov - 4 Nov
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 HK$3,257
HK$4,789 total
includes taxes & fees
1 Nov - 2 Nov
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.
A swimming pool with a stone border, surrounded by a snow-covered landscape and a wooden fence.

4. 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 HK$2,786
HK$3,463 total
includes taxes & fees
20 Oct - 21 Oct
Long Trail House at Stratton Mountain Resort
A building with a sign reading 'Fire Tower Restaurant & Tavern.'

5. 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
15 Oct - 16 Oct
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

6. 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
7 Oct - 8 Oct
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
A wooden cabin interior with a dining area, staircase, and a chandelier.

7. The Perfect Vermont Getaway! 3 bedroom, Fireplace, indoor Pool & Mountain Charm

The Perfect Vermont Getaway! 3 bedroom, Fireplace, indoor Pool & Mountain Charm
Wardsboro
10.0 out of 10, Exceptional, (2 reviews)
"Everything was wonderful and perfect for our family. Super clean and great Vermont experience"
United States
Lisa B.
The price is HK$1,949
HK$4,277 total
includes taxes & fees
21 Oct - 22 Oct
The Perfect Vermont Getaway! 3 bedroom, Fireplace, indoor Pool & Mountain Charm
A living room with a television, sofa, and coffee table.

8. Long Trail House South Wing 2B2B Condo

Long Trail House South Wing 2B2B Condo
Stratton
10.0 out of 10, Exceptional, (5 reviews)
"Very clean 2br 2ba condo in excellent location. Host provided detailed important information that helped us find property and how to access unit. I would definitely recommend staying here."
United States
Eileen R.
The price is HK$1,624
HK$3,839 total
includes taxes & fees
5 Nov - 6 Nov
Long Trail House South Wing 2B2B Condo
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, (36 reviews)
"Great space, great location!"
United States
Jason S.
The price is HK$1,632
HK$4,132 total
includes taxes & fees
26 Oct - 27 Oct
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
A wooden deck with a black Adirondack chair and a small table, surrounded by trees.

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$1,412
HK$3,449 total
includes taxes & fees
2 Nov - 3 Nov
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
A modern two-story house with a front porch, a staircase, and a driveway.

11. Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!

Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Jamaica
9.6 out of 10, Exceptional, (30 reviews)
"House was perfect for a guys trip for skiing. Just as expected. Would stay again. "
United States
Michael A.
The price is HK$2,113
HK$7,646 total
includes taxes & fees
14 Oct - 15 Oct
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
A spacious living room with a stone fireplace, wooden beams, and a large sofa.

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, (25 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$1,975
HK$5,087 total
includes taxes & fees
2 Nov - 3 Nov
Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
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 HK$1,096
HK$3,170 total
includes taxes & fees
14 Oct - 15 Oct
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
A living room with a sofa, a television, a fireplace, and a dining area with chairs and a table.

14. 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$2,462 total
includes taxes & fees
8 Oct - 9 Oct
Lovely ski-in/out condo steps from ski lift with trails and amazing views
A hallway with a bench, a wall-mounted towel rack, and a door leading to an outdoor area.

15. 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, (12 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$1,491
HK$3,946 total
includes taxes & fees
20 Oct - 21 Oct
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
A spacious living area with a gray sofa, a coffee table, and a kitchen area with a bar counter and stools.

16. Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!

Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!
Londonderry
10.0 out of 10, Exceptional, (11 reviews)
"Great location, well-designed house, and a beautiful view."
United States
Marcel P.
The price is HK$3,178
HK$6,642 total
includes taxes & fees
19 Oct - 20 Oct
Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!
A living room with a brick fireplace, a sofa, a chair, and a coffee table.

17. Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
Winhall
10.0 out of 10, Exceptional, (15 reviews)
"Clean, lots of room, easy access to Stratton, responsive host."
United States
Mark H.
The price is HK$3,139
HK$7,298 total
includes taxes & fees
20 Oct - 21 Oct
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
A modern living room with a fireplace, a large sofa set, and a view through the glass doors.

18. New! Vermont Getaway! Stratton - close to skiing!

New! Vermont Getaway! Stratton - close to skiing!
Winhall
10.0 out of 10, Exceptional, (1 review)
"The place was perfect for us! Easy stay. Very clean and the wood burning fireplace was great. Would def recommend!"
United States
Carolyn K.
The price is HK$2,425
HK$4,125 total
includes taxes & fees
3 Nov - 4 Nov
New! Vermont Getaway! Stratton - close to skiing!
A wooden cabin with a patio area featuring Adirondack chairs, a hot tub, and a fire pit.

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$2,150
HK$6,021 total
includes taxes & fees
12 Oct - 13 Oct
Luxe Chalet - Leaf Peeping, Near Mt Snow and Stratton Mountain w/Hot Tub, Sauna
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.

20. 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$1,922
HK$4,558 total
includes taxes & fees
12 Oct - 13 Oct
The MountainTop | Stratton & Mt Snow | Fire Pit
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

Brittany Motel

Brittany Motel

10/10 Excellent
"clean room, good snacks, and beautiful location."
Mary 1-night trip
Posted 8 hours ago
Brittany Motel

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 44 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.