A road flanked by dense bamboo groves.

Holiday 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
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 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 NZ$1,075
includes taxes & fees
29 Sept - 30 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.
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 NZ$436
includes taxes & fees
27 Sept - 28 Sept
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
A spacious kitchen with a large island, a stone fireplace, and wooden beams.

3. 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 NZ$1,288
includes taxes & fees
1 Oct - 2 Oct
Views for Days | Hot Tub, Sauna, EV, A/C | 6 Min to Stratton, 15 to Bromley
A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

4. 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, (41 reviews)
"Our family had a wonderful vacation. The house and location were great. We will come back."
United States
Victoria L.
The price is NZ$1,136
includes taxes & fees
24 Sept - 25 Sept
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.

5. 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 NZ$738
includes taxes & fees
24 Sept - 25 Sept
Modern Mount Snow Gnarvana - Steps to Carinthia
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 NZ$1,416
includes taxes & fees
29 Sept - 30 Sept
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
A snow-covered wooden cabin with a balcony, surrounded by snow-covered trees.

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

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is NZ$1,170
includes taxes & fees
29 Sept - 30 Sept
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
A garden with purple flowers and a river in the background.

8. 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 NZ$451
includes taxes & fees
29 Sept - 30 Sept
Family Friendly Hilltop House In Putney Vermont

9. 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 NZ$1,107
includes taxes & fees
24 Sept - 25 Sept
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
A two-story log cabin with a balcony on the upper level, surrounded by trees.

10. Charming 4-bedroom Ski house in Stratton with Shuttle or walk to slope.

Charming 4-bedroom Ski house in Stratton with Shuttle or walk to slope.
Stratton
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful stay! The location was extremely convenient to the mountain, and the house was clean, comfortable and spacious. We loved all of the seating in the living room, the large fireplace, and cozy hot tub."
United States
Steve M.
The price is NZ$2,650
includes taxes & fees
29 Sept - 30 Sept
Charming 4-bedroom Ski house in Stratton with Shuttle or walk to slope.
A cozy interior with a wooden ceiling, a large window, and a table with chairs.

11. 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, (20 reviews)
"Great place!"
United States
Jack & Heather G.
The price is NZ$960
includes taxes & fees
14 Oct - 15 Oct
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
A house with a deck, two Adirondack chairs, a glass-top table, and a barbecue grill.

12. Spacious Vermont Farmhouse | 3 Mi to Mount Snow

Spacious Vermont Farmhouse | 3 Mi to Mount Snow
West Dover
10.0 out of 10, Exceptional, (1 review)
"All good. "
United States
ken g.
The price is NZ$1,400
includes taxes & fees
28 Sept - 29 Sept
Spacious Vermont Farmhouse | 3 Mi to Mount Snow
A wooden barrel structure with a staircase and railing, surrounded by a forest.

13. 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 NZ$1,176
includes taxes & fees
26 Sept - 27 Sept
10 Mins to Mt Snow Golf Club-Game Room, Barrel Sauna, Hot Tub, Fire Pit, Dogs OK
A spacious kitchen with a large island, wooden ceiling beams, and a view to the outside.

14. 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 NZ$1,930
includes taxes & fees
19 Oct - 20 Oct
5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton
A pathway through a forest with autumn leaves and a wooden bridge.

15. Experience Vermont’s Fall Magic at here at the Lemondrop

Experience Vermont’s Fall Magic at here at the Lemondrop
Dover
10.0 out of 10, Exceptional, (46 reviews)
"Lovely house - perfect for a ski trip!"
United States
Alexander H.
The price is NZ$1,077
includes taxes & fees
24 Sept - 25 Sept
Experience Vermont’s Fall Magic at here at the Lemondrop

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 NZ$741
includes taxes & fees
28 Sept - 29 Sept
Charming Chester Farmhouse near Near VT Slopes
A modern kitchen with a built-in fireplace, wine storage, and a dining area with wooden furniture.

17. 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 NZ$2,049
includes taxes & fees
24 Sept - 25 Sept
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
A two-story house with a red roof, a front porch with a railing, and a gravel driveway.

18. The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
Woodford
The price is NZ$785
includes taxes & fees
28 Sept - 29 Sept
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
A two-story house with a deck, surrounded by dense forest.

19. 4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
Chester
10.0 out of 10, Exceptional, (5 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is NZ$1,713
includes taxes & fees
24 Sept - 25 Sept
4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
An outdoor dining area with tables and umbrellas, a wooden fence, and a building with large windows and lights.

20. Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.

Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.
Manchester
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful cozy house with plenty of beds and space. We drove here in a snowstorm and were so thankful that the host had cleared the driveway and walkways for us. Overall a great stay."
United States
Greg W.
The price is NZ$1,004
includes taxes & fees
19 Oct - 20 Oct
Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.
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 Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

10/10 Excellent
"The property is perfectly situated, just a short walk from Main Street, making it incredibly convenient for exploring the area. The location is excellent, and the hotel itself is very well-maintained and comfortable. I highly recommend it for anyone looking for a walkable base in the town."
Richard Del 2-night trip
Posted 3 hours ago
The Palmer House Resort, an Ascend Collection Hotel

Find out more about Jamaica

Jamaica Holiday Homes information

Number of reviews
209
Accommodation
830 Holiday Homes
Lowest Price
NZ$436
Highest Price
NZ$2,650