A road flanked by dense bamboo groves.

Holiday Homes in Jamaica

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Check prices for these dates

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

Our top choices for Jamaica holiday 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 AU$840
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 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 AU$363
includes taxes & fees
19 Oct - 20 Oct
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 AU$1,183
includes taxes & fees
20 Oct - 21 Oct
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 AU$238
includes taxes & fees
19 Oct - 20 Oct
The Eagles Wing at The CHM - Private Apartment
A rustic kitchen with wooden beams, a large island, and a hanging light fixture.

5. 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 AU$701
includes taxes & fees
27 Oct - 28 Oct
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
A living room with a brick fireplace, a sofa, a chair, and a coffee table.

6. 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 AU$1,144
includes taxes & fees
1 Nov - 2 Nov
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

7. 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 AU$949
includes taxes & fees
15 Oct - 16 Oct
Your Vermont Mountain Haven Pet Friendly home with 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.

8. 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 AU$645
includes taxes & fees
19 Oct - 20 Oct
Modern Mount Snow Gnarvana - Steps to Carinthia
A spacious room with wooden beams, large windows, and a cozy seating area with white furniture.

9. 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 AU$1,676
includes taxes & fees
2 Nov - 3 Nov
Gorgeous couples barn with WiFi & hot tub in lovely Londonderry
A spacious kitchen with a large island, wooden ceiling beams, and a view to the outside.

10. 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 AU$1,494
includes taxes & fees
19 Oct - 20 Oct
5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton
A wooden barrel structure with a staircase and railing, surrounded by a forest.

11. 10 Mins to Mt Snow Golf Club-Game Room, Barrel Sauna, Hot Tub, Fire Pit, Dogs OK

10 Mins to Mt Snow Golf Club-Game Room, Barrel Sauna, Hot Tub, Fire Pit, Dogs OK
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 AU$944
includes taxes & fees
10 Nov - 11 Nov
10 Mins to Mt Snow Golf Club-Game Room, Barrel Sauna, Hot Tub, Fire Pit, Dogs OK
Exterior

12. 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 AU$1,018
includes taxes & fees
15 Oct - 16 Oct
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.

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

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is AU$932
includes taxes & fees
20 Oct - 21 Oct
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
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 AU$882
includes taxes & fees
18 Oct - 19 Oct
Cozy 3 Bedroom Condo in the Heart of Manchester VT
A modern kitchen with a built-in fireplace, wine storage, and a dining area with wooden furniture.

15. 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 AU$1,660
includes taxes & fees
15 Oct - 16 Oct
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
A garden with a wooden pergola, purple flowers, and a river view.

16. 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 AU$369
includes taxes & fees
20 Oct - 21 Oct
Family Friendly Hilltop House In Putney Vermont
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 AU$152
includes taxes & fees
30 Oct - 31 Oct
Cozy Vermont Tiny Home Get Away
Dining

18. 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 AU$592
includes taxes & fees
5 Nov - 6 Nov
Charming Chester Farmhouse near Near VT Slopes
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 AU$1,103
includes taxes & fees
21 Oct - 22 Oct
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 AU$794
includes taxes & fees
19 Oct - 20 Oct
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.
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Top Jamaica Hotel Reviews

Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

8/10 Good
"The accommodations were very good but was disappointed that they made us pay $20 to park for the day we were leaving because we asked to stay in the lobby for an extra hour until we could pick up our grandson up at a neighboring ski camp. Especially since the parking lot was not full & we were there for four nights."
Timothy 4-night trip
Posted 3 hours ago
Grand Summit Resort, A Vail Resorts Property

Find out more about Jamaica

Jamaica Holiday Homes information

Number of reviews
144
Accommodation
819 Holiday Homes
Lowest Price
AU$152
Highest Price
AU$1,660

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