A road flanked by dense bamboo groves.

Holiday Homes in Jamaica

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Jamaica holiday homes

Exterior

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 €535
includes taxes & fees
24 Jul - 25 Jul
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.
Interior

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 €242
includes taxes & fees
29 Jul - 30 Jul
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Exterior

Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
Jamaica
9.6 out of 10, Exceptional, (26 reviews)
"We enjoyed our stay at a great ski house that was in a good location to the mountain. Accommodations were comfortable for 6 adults and 4 kids and the shuffleboard, foosball and pool tables were a hit. "
United States
Jonathan H.
The price is €778
includes taxes & fees
29 Jul - 30 Jul
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
Exterior detail

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 €946
includes taxes & fees
17 Aug - 18 Aug
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Outdoor spa tub

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, (39 reviews)
"House was clean and pet-friendly! Great location between Bromley and Stratton!"
United States
Michael I.
The price is €601
includes taxes & fees
29 Jul - 30 Jul
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
TV, fireplace, books, music library

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, (12 reviews)
The price is €852
includes taxes & fees
28 Jul - 29 Jul
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
Exterior

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 €574
includes taxes & fees
26 Jul - 27 Jul
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
Interior

Private Cabin 4BR 3BA, Fire pit, Pool table, BBQ Weber, Babbling Brook, Cornhole

Private Cabin 4BR 3BA, Fire pit, Pool table, BBQ Weber, Babbling Brook, Cornhole
Dover
The price is €470
includes taxes & fees
27 Jul - 28 Jul
Private Cabin 4BR 3BA, Fire pit, Pool table, BBQ Weber, Babbling Brook, Cornhole
Terrace/patio

3 Mi to Mount Snow: Spacious West Dover Home

3 Mi to Mount Snow: Spacious West Dover Home
West Dover
10.0 out of 10, Exceptional, (1 review)
"All good. "
United States
ken g.
The price is €609
includes taxes & fees
24 Jul - 25 Jul
3 Mi to Mount Snow: Spacious West Dover Home
Property grounds

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (62 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is €261
includes taxes & fees
27 Jul - 28 Jul
Family Friendly Hilltop House In Putney Vermont
Coffee/tea maker, fridge, microwave, oven

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 €1,021
includes taxes & fees
27 Jul - 28 Jul
5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton
Exterior

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

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, (19 reviews)
"Great place!"
United States
Jack & Heather G.
The price is €502
includes taxes & fees
19 Aug - 20 Aug
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Dining

Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes
Chester Depot
9.4 out of 10, Exceptional, (22 reviews)
"We had a great stay! The house was clean, comfortable, and exactly as described. The location was perfect and the host was very responsive. We’d definitely stay here again and highly recommend it."
United States
Stephanie F.
The price is €362
includes taxes & fees
30 Jul - 31 Jul
Charming Chester Farmhouse near Near VT Slopes
Property grounds

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, (10 reviews)
"Awesome place, fantastic amenities and easy to get to. Looking forward to coming back."
United States
Connor S.
The price is €668
includes taxes & fees
17 Aug - 18 Aug
10 Mins to Mt Snow Golf Club-Game Room, Barrel Sauna, Hot Tub, Fire Pit, Dogs OK
Smart TV, fireplace, video games, DVD player

Summer Escape Near Lakes, Trails & Mt Snow

Summer Escape Near Lakes, Trails & Mt Snow
Dover
10.0 out of 10, Exceptional, (44 reviews)
The price is €588
includes taxes & fees
3 Aug - 4 Aug
Summer Escape Near Lakes, Trails & Mt Snow
Coffee/tea maker, fridge, microwave, oven

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 €1,050
includes taxes & fees
24 Jul - 25 Jul
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Terrace/patio

Okemo's Back Room - in the heart of the village on the shuttle route!

Okemo's Back Room - in the heart of the village on the shuttle route!
Ludlow
9.6 out of 10, Exceptional, (16 reviews)
"Cool building, right on main street. Building is undergoing renovation on back porches so some construction material and disruption. The kitchen was not well equiped and needs an update. However, the space is really cool, very open, big bedrooms, decent bedding. Shower is a little small but nice. Good value"
United States
jonathan w.
The price is €352
includes taxes & fees
27 Jul - 28 Jul
Okemo's Back Room - in the heart of the village on the shuttle route!
Outdoor dining

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, (11 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 €474
includes taxes & fees
27 Jul - 28 Jul
Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.
Coffee/tea maker, fridge, microwave, oven

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Ludlow
9.8 out of 10, Exceptional, (113 reviews)
"Clean great cozy place!"
United States
Himanshu P.
The price is €393
includes taxes & fees
26 Jul - 27 Jul
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
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

Colonial Motel

Colonial Motel

10/10 Excellent
"A Good Value Motel under New Owners ! A Good Value !"
Donald 1-night trip
Posted 1 hour ago
Colonial Motel

Find out more about Jamaica

Jamaica Holiday Homes information

Number of reviews
308
Accommodation
867 Holiday Homes
Lowest Price
€242
Highest Price
€1,050