Book Holiday Homes in Jamaica

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Featured Holiday Homes in Jamaica

Secluded home with game room, private hot tub, golf, river & mtn views, firepit

Secluded home with game room, private hot tub, golf, river & mtn views, firepit

Manchester
Book a stay at this golf vacation home in Manchester Center. Enjoy a water park, a garden, and a pool table. Popular attractions Dana L. Thompson Memorial Park ...
Secluded home with game room, private hot tub, golf, river & mtn views, firepit
Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer

Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer

Stratton
Book a stay at this ski vacation home in Stratton. Enjoy a garden, ski-in/ski-out access, and patios. Popular attractions Stratton Mountain Resort and Stratton ...
Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

Dorset
Stay at this vacation home in Rupert. Enjoy free WiFi, a garden, and patios. Popular attractions Dorset Historical Society Museum and Dorset Playhouse are located ...
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
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Potter's Place | House in Jamaica with mountain views

Potter's Place | House in Jamaica with mountain views

Jamaica
Stay at this vacation home in Jamaica. Enjoy patios, an in-room coffeemaker, and in-room fireplaces. Popular attractions Hot Glass Works and Ball Mountain State ...
Potter's Place | House in Jamaica with mountain views
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Ludlow
Stay at this vacation home in Ludlow. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Okemo Mountain Resort and Sachem ...
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Dover
Book a stay at this ski vacation home in West Dover. Enjoy free WiFi, a garden, and ski-in/ski-out access. Popular attractions Mount Snow and Heavy Metal Ski ...
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
Cozy retreat near slopes

Cozy retreat near slopes

Dover
Stay at this vacation home in West Dover. Enjoy a sauna and an indoor pool. Popular attractions Mount Snow and Discovery Shuttle Ski Lift are located ...
Cozy retreat near slopes
GAMERS HAVEN, River Wine Inn!

GAMERS HAVEN, River Wine Inn!

2 out of 5
Whitingham
Book a stay at this family-friendly vacation home in Jacksonville. Enjoy a fitness center, a pool table, and cable/satellite TV service. Popular attractions ...
GAMERS HAVEN, River Wine Inn!
Walk to Okemo Ski Lift - Private Classic VT Ski Chalet w/ Fire Pit & Pool Table

Walk to Okemo Ski Lift - Private Classic VT Ski Chalet w/ Fire Pit & Pool Table

Ludlow
Book a stay at this ski vacation home in Ludlow. Enjoy free WiFi, a garden, and ski-in/ski-out access. Popular attractions Okemo Mountain Resort and Sunshine ...
Walk to Okemo Ski Lift - Private Classic VT Ski Chalet w/ Fire Pit & Pool Table
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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.

Jamaica Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Jamaica vacation homes are the perfect way for you to wing it.

Holiday houses in Jamaica let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Jamaica in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Jamaica adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Jamaica with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Jamaica vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Jamaica Holiday Homes essential information

Accommodation
924 Holiday Homes
Lowest Price
NZ$202
Highest Price
NZ$304
Popular accommodation
Secluded home with game room, private hot tub, golf, river & mtn views, firepit, Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer, Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style, Potter's Place | House in Jamaica with mountain views, Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable, Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit. , Cozy retreat near slopes, GAMERS HAVEN, River Wine Inn!, Walk to Okemo Ski Lift - Private Classic VT Ski Chalet w/ Fire Pit & Pool Table

Top trending hotels in Jamaica

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
3567 Main Street Route 7A, Manchester, VT
Fully refundableReserve now, pay when you stay
The price is NZ$304 per night from 9 Apr to 10 Apr
NZ$304
includes taxes & fees
9 Apr - 10 Apr
Stay at this 4.5-star luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the property condition in our ...
The Equinox Golf Resort & Spa
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

2.5 out of 5
4519 Main St, Manchester Center, VT
Fully refundableReserve now, pay when you stay
The price is NZ$257 per night from 29 Apr to 30 Apr
NZ$257
includes taxes & fees
29 Apr - 30 Apr
Book a stay at this business-friendly hotel in Manchester Center. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the ...
Hampton Inn and Suites Manchester
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is NZ$207 per night from 6 Apr to 7 Apr
NZ$207
includes taxes & fees
6 Apr - 7 Apr
Stay at this 3-star spa motel in Brattleboro. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff and the clean rooms in our ...
Colonial Motel And Spa
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Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is NZ$202 per night from 28 Apr to 29 Apr
NZ$202
includes taxes & fees
28 Apr - 29 Apr
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the ...
Hampton Inn Brattleboro
Don't see what you're looking for?
See all available properties in Jamaica
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.