A road flanked by dense bamboo groves.

Search Vacation Homes in Jamaica

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Jamaica vacation homes

A lodge with a large fireplace, a covered porch, and a staircase leading to the upper level.

1. 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 ￥65,699
￥96,978 total
includes taxes & fees
Nov 1 - Nov 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.
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

2. 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 ￥11,802
￥40,540 total
includes taxes & fees
Oct 13 - Oct 14
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
A modern two-story house with a front porch, a staircase, and a driveway.

3. 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 ￥29,455
￥137,220 total
includes taxes & fees
Oct 19 - Oct 20
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
A bedroom with a large bed, a window with blinds, a bookshelf, and a wall-mounted ship's wheel.

4. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.6 out of 10, Exceptional, (5 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
The price is ￥18,997
￥25,044 total
includes taxes & fees
Oct 15 - Oct 16
The Eagles Wing at The CHM - Private Apartment
A living room with a brick fireplace, a sofa, a chair, and a coffee table.

5. 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 ￥53,825
￥135,956 total
includes taxes & fees
Oct 28 - Oct 29
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
A rustic kitchen with wooden beams, a large island, and a hanging light fixture.

6. Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Londonderry
7.0 out of 10, Good, (2 reviews)
"I was "sold" & excited when I saw the pictures online bc the barn looked really neat. Although the barn was a neat concept, the pictures ARE NOT accurate, it is not as updated as pictured & it was VERY DISAPPOINTING. I now understand the non-refundable policy bc what you see online is definitely NOT what you walked into when you opened the door & they don't want to have to give people their back. Although we had fun, the accommodations were VERY misleading & disappointing. "
United States
Christine M.
The price is ￥40,179
￥79,570 total
includes taxes & fees
Oct 13 - Oct 14
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
A spacious indoor area with multiple wooden tables and green chairs, large windows offering a view of a snowy mountain, and a stone fireplace with a fire.

7. Modern Mount Snow Gnarvana - Steps to Carinthia

Modern Mount Snow Gnarvana - Steps to Carinthia
Dover
10.0 out of 10, Exceptional, (26 reviews)
"Perfect for our getaway, convenient for getting to the slopes and a beautiful area to visit"
United States
Lynn B.
The price is ￥32,200
￥80,035 total
includes taxes & fees
Oct 17 - Oct 18
Modern Mount Snow Gnarvana - Steps to Carinthia
A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

8. Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Winhall
9.4 out of 10, Exceptional, (43 reviews)
"Our family had a wonderful vacation. The house and location were great. We will come back."
United States
Victoria L.
The price is ￥31,242
￥104,962 total
includes taxes & fees
Oct 13 - Oct 14
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
A spacious kitchen with a large island, wooden ceiling beams, and a view to the outside.

9. 5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton

5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton
Stratton
10.0 out of 10, Exceptional, (20 reviews)
"Great spot for a large group. "
United States
Brian G.
The price is ￥70,765
￥168,665 total
includes taxes & fees
Nov 1 - Nov 2
5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton
A wooden barrel structure with a staircase and railing, surrounded by a forest.

10. Dover Mountain Retreat with Hot Tub Near Mt. Snow

Dover Mountain Retreat with Hot Tub Near Mt. Snow
Dover
10.0 out of 10, Exceptional, (11 reviews)
"Awesome place, fantastic amenities and easy to get to. Looking forward to coming back."
United States
Connor S.
The price is ￥49,231
￥112,287 total
includes taxes & fees
Nov 10 - Nov 11
Dover Mountain Retreat with Hot Tub Near Mt. Snow
Exterior

11. Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
Andover
10.0 out of 10, Exceptional, (1 review)
"Very nice stay. Owners were very gracious. House was clean & comfortable."
United States
Lorraine C.
The price is ￥44,327
￥111,526 total
includes taxes & fees
Oct 13 - Oct 14
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
A bedroom with a wooden headboard, a bed with patterned bedding, and a framed picture on the wall.

12. MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is ￥35,319
￥105,713 total
includes taxes & fees
Nov 2 - Nov 3
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
A spacious room with wooden beams, large windows, and a cozy seating area with white furniture.

13. Gorgeous couples barn with WiFi & hot tub in lovely Londonderry

Gorgeous couples barn with WiFi & hot tub in lovely Londonderry
Londonderry
10.0 out of 10, Exceptional, (2 reviews)
"The converted barn was absolutely stunning. Kitchen was well appointed and the family room spacious and comfortible."
United States
Tim M.
The price is ￥126,379
￥193,792 total
includes taxes & fees
Nov 3 - Nov 4
Gorgeous couples barn with WiFi & hot tub in lovely Londonderry
A room with a large window, a wooden table, two chairs, and a woven basket on the table.

14. Cozy 3 Bedroom Condo in the Heart of Manchester VT

Cozy 3 Bedroom Condo in the Heart of Manchester VT
Manchester
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful place Very spacious and super organized we love our stay "
United States
Rafael
The price is ￥34,195
￥86,983 total
includes taxes & fees
Oct 15 - Oct 16
Cozy 3 Bedroom Condo in the Heart of Manchester VT
A garden with a wooden pergola, purple flowers, and a river view.

15. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (64 reviews)
"The house was all we expected. Very comfortable and ready for us when we arrived. It’s a bit out of the way, at the end of a private road, but quiet and secluded. Our host was attentive without being intrusive. She clearly wanted to make sure our stay met our expectations and was pleasant. All in all, a delightful way to visit Vermont!"
United States
Susan G.
The price is ￥20,802
￥40,320 total
includes taxes & fees
Oct 20 - Oct 21
Family Friendly Hilltop House In Putney Vermont
Dining

16. Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes
Chester Depot
9.4 out of 10, Exceptional, (22 reviews)
"Beautiful classic farmhouse in lovely neighbourhood."
United States
Kimberly B.
The price is ￥33,087
￥66,845 total
includes taxes & fees
Nov 5 - Nov 6
Charming Chester Farmhouse near Near VT Slopes
A compact kitchen with a red bench, a microwave, a sink, and a window with a view of a snowy landscape.

17. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
The price is ￥11,398
￥16,458 total
includes taxes & fees
Oct 31 - Nov 1
Cozy Vermont Tiny Home Get Away
A modern kitchen with a built-in fireplace, wine storage, and a dining area with wooden furniture.

18. Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Dover
10.0 out of 10, Exceptional, (13 reviews)
"great location easy access to the mountain and the pool was outstanding."
United States
jim f.
The price is ￥73,377
￥186,675 total
includes taxes & fees
Oct 13 - Oct 14
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
A spacious kitchen with a central island, stainless steel appliances, and pendant lighting.

19. 1812 House, 2 Stays, 1 home

1812 House, 2 Stays, 1 home
Manchester
The price is ￥46,936
￥120,837 total
includes taxes & fees
Nov 3 - Nov 4
1812 House, 2 Stays, 1 home
A cozy interior with a wooden ceiling, a large window, and a table with chairs.

20. VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Wilmington
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful home and property with quick access to a clubhouse with a gym, indoor and outdoor pools, and hot tub. Great for our family trip (including two kids) and lots of games/entertainment for the kids. The house had everything we needed (including kitchenware needed for cooking and preparing food)."
United States
Natalie
The price is ￥31,029
￥90,584 total
includes taxes & fees
Oct 13 - Oct 14
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Jamaica Hotel Reviews

The White House Inn

The White House Inn

10/10 Excellent
"Very clean and staff was amazing."
Rita 2-night trip
Posted 9 hours ago
The White House Inn

Find out more about Jamaica

Jamaica Vacation Homes information

Number of reviews
144
Accommodation
829 Vacation Homes
Lowest Price
￥16,458
Highest Price
￥186,675