Book Holiday Homes in Jamaica

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Featured Holiday Homes in Jamaica

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
The price is AU$558 per night from 3 Dec to 4 Dec
AU$558
includes taxes & fees
3 Dec - 4 Dec
With a stay at this vacation home in Ludlow, you'll be in the mountains, within a 5-minute drive of Okemo Mountain Resort and Dorsey Park.
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Plenty of Room For Everyone! - 5 Minutes to Stratton

Plenty of Room For Everyone! - 5 Minutes to Stratton

Jamaica
The price is AU$1,330 per night from 25 Nov to 26 Nov
AU$1,330
includes taxes & fees
25 Nov - 26 Nov
With a stay at this vacation home in Winhall, you'll be on a river, within a 10-minute drive of Stratton Mountain Resort and Green Mountain National Forest.
Plenty of Room For Everyone! - 5 Minutes to Stratton
Okemo Mountain Lodging

Okemo Mountain Lodging

3.5 out of 5
77 Okemo Ridge Rd, Ludlow, VT
With a stay at Okemo Mountain Lodging in Ludlow (Clock Tower Base Area), you'll be within a 10-minute walk of Okemo Mountain Resort and General Parking.
Okemo Mountain Lodging
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Miner Cottage-Historic Antique Home just steps from the Equinox Resort

Miner Cottage-Historic Antique Home just steps from the Equinox Resort

Manchester
Located in Manchester, this vacation home is next to a golf course, within a 5-minute walk of Green Mountain National Forest and Golf Club at Equinox.
Miner Cottage-Historic Antique Home just steps from the Equinox Resort
Dog-friendly chalet cabin with valley view, deck, and private hot tub

Dog-friendly chalet cabin with valley view, deck, and private hot tub

Wardsboro
With a stay at this vacation home in Wardsboro, you'll be within a 15-minute drive of Mount Snow and Green Mountain National Forest.
Dog-friendly chalet cabin with valley view, deck, and private hot tub
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

Whitingham
Located in Whitingham, this vacation home is on the waterfront, within a 15-minute walk of Harriman Reservoir and Green Mountain National Forest.
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Beautiful!! Bromley-Stratton VT Slopeside Ski Home, Minutes from Manchester

Beautiful!! Bromley-Stratton VT Slopeside Ski Home, Minutes from Manchester

Peru
With a stay at this vacation home in Peru (Bromley Mountain), you'll be steps from Green Mountain National Forest and 8 minutes by foot from Bromley Mountain ...
Beautiful!! Bromley-Stratton VT Slopeside Ski Home, Minutes from Manchester
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

Townshend
Located in Townshend, this vacation home is on the waterfront, a 1-minute drive from West River and 8 minutes from Townshend State Park.
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Cozy ski retreat on the Stratton Access Road - 5 minutes to the slope!

Cozy ski retreat on the Stratton Access Road - 5 minutes to the slope!

Winhall
With a stay at this vacation home in Winhall, you'll be within a 5-minute drive of Stratton Mountain Resort and Green Mountain National Forest.
Cozy ski retreat on the Stratton Access Road - 5 minutes to the slope!
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See all available properties in Jamaica
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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
757 Holiday Homes
Lowest Price
AU$178
Highest Price
AU$1,330
Popular accommodation
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle, Plenty of Room For Everyone! - 5 Minutes to Stratton, Okemo Mountain Lodging, Miner Cottage-Historic Antique Home just steps from the Equinox Resort, Dog-friendly chalet cabin with valley view, deck, and private hot tub, Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating , Beautiful!! Bromley-Stratton VT Slopeside Ski Home, Minutes from Manchester, Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns, Cozy ski retreat on the Stratton Access Road - 5 minutes to the slope!

Top trending hotels in Jamaica

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 AU$233 per night from 8 Dec to 9 Dec
AU$233
includes taxes & fees
8 Dec - 9 Dec
A stay at Hampton Inn and Suites Manchester places you in the heart of Manchester Center, steps from Green Mountain National Forest and 8 minutes by foot from ...
Hampton Inn and Suites Manchester
Kimpton Taconic Hotel, an IHG Hotel

Kimpton Taconic Hotel, an IHG Hotel

4 out of 5
3835 Main St., Manchester, VT
Fully refundable
The price is AU$338 per night from 16 Dec to 17 Dec
AU$338
includes taxes & fees
16 Dec - 17 Dec
With a stay at Kimpton Taconic Hotel, an IHG Hotel in Manchester, you'll be next to a golf course, just a 1-minute walk from Green Mountain National Forest and ...
Kimpton Taconic Hotel, an IHG Hotel
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 AU$178 per night from 3 Dec to 4 Dec
AU$178
includes taxes & fees
3 Dec - 4 Dec
A stay at Colonial Motel And Spa places you in the heart of Brattleboro, steps from Brattleboro Bowl and 11 minutes by foot from New England Center for Circus ...
Colonial Motel And Spa
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Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103, Cavendish, VT
The price is AU$271 per night from 22 Nov to 23 Nov
AU$271
includes taxes & fees
22 Nov - 23 Nov
With a stay at Pointe at Castle Hill Resort in Cavendish, you'll be near ski lifts, within a 10-minute drive of Okemo Mountain Resort and Fletcher Farm School ...
Pointe at Castle Hill Resort
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.