Book Holiday Homes in Jamaica

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Featured Holiday Homes in Jamaica

Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!

Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!

Dover
The price is AU$575 per night from 25 Mar to 26 Mar
AU$575
includes taxes & fees
25 Mar - 26 Mar
With a stay at this vacation home in West Dover, you'll be in the mountains, within a 5-minute drive of Mount Snow and Green Mountain National Forest.
Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!
Beautiful! 5 Beds-5 baths Home, Spectacular Views of Stratton, On Shuttle

Beautiful! 5 Beds-5 baths Home, Spectacular Views of Stratton, On Shuttle

Stratton
With a stay at this vacation home in Winhall, you'll be in the mountains, within a 10-minute drive of Stratton Mountain Resort and Green Mountain National ...
Beautiful! 5 Beds-5 baths Home, Spectacular Views of Stratton, On Shuttle
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
When you stay at this vacation home in West Dover, you'll be in the mountains, within a 15-minute walk of Mount Snow and Green Mountain National Forest.
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
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Ski-In condo at Mount Snow with Fireplace, Bears Crossing

Ski-In condo at Mount Snow with Fireplace, Bears Crossing

Dover
With a stay at this vacation home in West Dover, you'll be in the mountains, within a 5-minute drive of Mount Snow and Green Mountain National Forest.
Ski-In condo at Mount Snow with Fireplace, Bears Crossing
Spacious Townhome with breathtaking views of Mount Snow. 5 min Shuttle to ski

Spacious Townhome with breathtaking views of Mount Snow. 5 min Shuttle to ski

Dover
With a stay at this vacation home in West Dover, you'll be next to a golf course, within a 5-minute drive of Mount Snow and North Branch Deerfield River.
Spacious Townhome with breathtaking views of Mount Snow. 5 min Shuttle to ski
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Winhall
The price is AU$1,577 per night from 23 Feb to 24 Feb
AU$1,577
includes taxes & fees
23 Feb - 24 Feb
With a stay at this vacation home in Winhall, you'll be in the mountains, within a 10-minute drive of Bromley Mountain Ski Resort and Green Mountain National ...
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
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$736 per night from 25 Mar to 26 Mar
AU$736
includes taxes & fees
25 Mar - 26 Mar
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
Secluded Rustic Home with Private Hot Tub & Huge Deck - 5 Miles to Okemo

Secluded Rustic Home with Private Hot Tub & Huge Deck - 5 Miles to Okemo

Ludlow
With a stay at this vacation home, you'll be centrally located in Ludlow, within a 15-minute drive of Okemo Mountain Resort and Green Mountain National ...
Secluded Rustic Home with Private Hot Tub & Huge Deck - 5 Miles to Okemo
Vermont's Mountain Villa: Hot tub, Ski views, Pet+

Vermont's Mountain Villa: Hot tub, Ski views, Pet+

Andover
Located in Ludlow, this vacation home is in the mountains, within a 15-minute drive of Mill Museum and Weston Playhouse.
Vermont's Mountain Villa: Hot tub, Ski views, Pet+
Don't see what you're looking for?
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
790 Holiday Homes
Lowest Price
AU$189
Highest Price
AU$1,577
Popular accommodation
Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!, Beautiful! 5 Beds-5 baths Home, Spectacular Views of Stratton, On Shuttle, Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit. , Ski-In condo at Mount Snow with Fireplace, Bears Crossing, Spacious Townhome with breathtaking views of Mount Snow. 5 min Shuttle to ski, Your Vermont Mountain Haven Pet Friendly home with Hot tub!, Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle, Secluded Rustic Home with Private Hot Tub & Huge Deck - 5 Miles to Okemo, Vermont's Mountain Villa: Hot tub, Ski views, Pet+

Top trending hotels in Jamaica

Mountaineer Inn

Mountaineer Inn

2 out of 5
270 Handle Rd, West Dover, VT
Fully refundableReserve now, pay when you stay
The price is AU$234 per night from 4 Mar to 5 Mar
AU$234
includes taxes & fees
4 Mar - 5 Mar
When you stay at Mountaineer Inn in West Dover, you'll be near ski lifts, within a 15-minute walk of Mount Snow and Green Mountain National Forest.
Mountaineer Inn
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$328 per night from 5 Mar to 6 Mar
AU$328
includes taxes & fees
5 Mar - 6 Mar
With a stay at Kimpton Taconic Hotel by IHG in Manchester, you'll be next to a golf course, just a 1-minute walk from Green Mountain National Forest and 6 minutes ...
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$189 per night from 23 Feb to 24 Feb
AU$189
includes taxes & fees
23 Feb - 24 Feb
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$301 per night from 25 Mar to 26 Mar
AU$301
includes taxes & fees
25 Mar - 26 Mar
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.