Holiday Rentals in Jamaica

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Our top choices for Jamaica holiday rentals

Cabin-7 minutes to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dog OK

Cabin-7 minutes to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dog OK
2.0 star property
Jamaica
10.0 out of 10, Exceptional, (5)
"Great stay"
United States
Chelsea D.
The price is €196
includes taxes & fees
4 Jan - 5 Jan 2026
Cabin-7 minutes to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dog OK

Stratton A-Frame: Boot Warmers EV Hot Tub Sauna,1 Gbps, Manchester Okemo MT Snow

Stratton A-Frame: Boot Warmers EV Hot Tub Sauna,1 Gbps, Manchester Okemo MT Snow
Jamaica
The price is €690
includes taxes & fees
5 Jan - 6 Jan 2026
Stratton A-Frame: Boot Warmers EV Hot Tub Sauna,1 Gbps, Manchester Okemo MT Snow

Family-friendly A-Frame near Stratton, Bromley & Magic — hot tub retreat in the quiet, peaceful woods

Family-friendly A-Frame near Stratton, Bromley & Magic — hot tub retreat in the quiet, peaceful woods
Jamaica
9.0 out of 10, Wonderful, (6)
"Great location. House was recently updated but has some older charm in parts. Fun and cozy. Hot tub was great the first day but smell seemed off the next day. Perhaps more chlorine was needed. Great time , great trip. Pet friendly is a bonus and the house looks never used so the cleaning crew is doing great work. Will rent again next year perhaps !"
United States
Michael C.
The price is €677
includes taxes & fees
5 Jan - 6 Jan 2026
Family-friendly A-Frame near Stratton, Bromley & Magic — hot tub retreat in the quiet, peaceful woods

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.2 out of 10, Wonderful, (17)
"So cute and in such a great area! It was a perfect stay"
United States
Jaden F.
The price is €261
includes taxes & fees
5 Jan - 6 Jan 2026
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

Lake Whitingham & Mount Snow Area Village Apartment

Lake Whitingham & Mount Snow Area Village Apartment
2.0 star property
Whitingham
10.0 out of 10, Exceptional, (1)
"This place was cozy and romantic, making it the perfect escape from the hustle and bustle of city life. The location is ideal, with charming New England towns to explore in every direction. Amy and Connor were exceptional hosts, checking in with us throughout our stay to ensure we felt right at home."
United States
Anicia K.
The price is €265
includes taxes & fees
29 Dec - 30 Dec
Lake Whitingham & Mount Snow Area Village Apartment

Wellness Getaway with a Personal Sauna, and Private River Beach!

Wellness Getaway with a Personal Sauna, and Private River Beach!
2.0 star property
Newfane
10.0 out of 10, Exceptional, (2)
"The folks are SUPER and made me feel very welome"
United States
Mark
The price is €221
includes taxes & fees
19 Jan - 20 Jan 2026
Wellness Getaway with a Personal Sauna, and Private River Beach!

Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.8 out of 10, Exceptional, (8)
"As always, an excellent stay. Wonderful unit, very nicely stocked in a perfect location. Communication was quick and easy. Easily my favorite place to stay!"
United States
Vanessa P.
The price is €293
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy Bromley Retreat

Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort
3.0 star property
Stratton
8.4 out of 10, Very good, (78)
"The building and the units are old and tired. Early attic decorating. And the walls are paper thin. We could hear all neighbors. I would not go back. "
United States
Doug
The price is €428
includes taxes & fees
5 Jan - 6 Jan 2026
Long Trail House at Stratton Mountain Resort

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Clock Tower Base Area
9.0 out of 10, Wonderful, (74)
"Perfect location for a quick ski trip. "
United States
Michael D.
The price is €280
includes taxes & fees
11 Jan - 12 Jan 2026
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow
West Dover
9.0 out of 10, Wonderful, (45)
"Great quiet location, kitchen had enough essentials for basic cooking to be easy. The king bed was comfortable and the living room is a great hangout spot."
United States
Franklin C.
Cozy 3 bedroom condo 2.5 miles to Mount Snow

Whimsical Room & Private Bathroom in Historic Inn

Whimsical Room & Private Bathroom in Historic Inn
Chester Depot
8.8 out of 10, Excellent, (9)
"After a long month of work I needed a weekend in VT to calm the nerves. This was a beautiful spot to be in, glad I was here!"
United States
Paul S.
The price is €177
includes taxes & fees
4 Jan - 5 Jan 2026
Whimsical Room & Private Bathroom in Historic Inn

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Dover
9.8 out of 10, Exceptional, (22)
"Decently-sized rooms, great lighting, plenty of space for families with kids to relax, enjoy the outdoor space, easy drive to Stratton and Wilmington. "
United States
SZU YIN C.
The price is €352
includes taxes & fees
5 Jan - 6 Jan 2026
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

Wilmington Retreat Near Trails, Skiing & Festivals

Wilmington Retreat Near Trails, Skiing & Festivals
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (2)
"Great location and awesome house. Owners were easy to communicate with. "
United States
Anonymous traveller
Wilmington Retreat Near Trails, Skiing & Festivals

Beautiful country cabin with hot tub and outdoor shower in Londonderry

Beautiful country cabin with hot tub and outdoor shower in Londonderry
2.0 star property
Londonderry
10.0 out of 10, Exceptional, (2)
"On a farm in the country…..stars blazing at night for hot tub. Cozy loft had amazing mattress and pillows! Our dog enjoyed the surrounding field. Beautiful! "
United States
Laurel
The price is €314
includes taxes & fees
29 Dec - 30 Dec
Beautiful country cabin with hot tub and outdoor shower in Londonderry

Mountain Dream Escape

Mountain Dream Escape
2.0 star property
Sandgate
10.0 out of 10, Exceptional, (1)
"Beautiful location and home! The apartment was beautifully decorated and so cozy. The hot tub was a great place for stargazing! It was wonderful for our anniversary weekend but would also be great for a longer stay.Great communication with hosts and they were super helpful when we had a minor issue with check in."
United States
Morgan C.
Mountain Dream Escape

Chester Farmhouse Ski Retreat near Slopes

Chester Farmhouse Ski Retreat near Slopes
Chester Depot
9.6 out of 10, Exceptional, (17)
"This was my second time staying at this property. Everything was great just like last year. I highly recommend it if you are staying in Chester, VT. "
United States
Lori N.
The price is €291
includes taxes & fees
20 Jan - 21 Jan 2026
Chester Farmhouse Ski Retreat near Slopes

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
7.6 out of 10, Good, (53)
"Irish Bar nearby was a plus on St. Patrick’s Day !"
United States
Warren
The price is €340
includes taxes & fees
14 Jan - 15 Jan 2026
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location
Ludlow
8.6 out of 10, Excellent, (32)
"Nice place close to mountain easy in easy out"
United States
Aaron B.
The price is €232
includes taxes & fees
5 Jan - 6 Jan 2026
Efficient condo near slopes with kitchenette & great location

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Dover
8.8 out of 10, Excellent, (32)
"Very nice accommodations and location!"
United States
Michael M.
The price is €397
includes taxes & fees
21 Jan - 22 Jan 2026
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Mountain Chalet mins from Mt Snow Skiing/hiking

Mountain Chalet mins from Mt Snow Skiing/hiking
East Dover
9.8 out of 10, Exceptional, (9)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is €387
includes taxes & fees
5 Jan - 6 Jan 2026
Mountain Chalet mins from Mt Snow Skiing/hiking
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

Find out more about Jamaica

Everything you need to know about Jamaica holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Jamaica holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Jamaica holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Jamaica holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Jamaica. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Jamaica holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Jamaica holiday rentals we have selected for you start as low as €280 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Jamaica rentals

At Expedia, we put the best Jamaica holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Jamaica rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Jamaica holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Jamaica. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Jamaica?

Yes, there are holiday rentals close to the most popular sights in Jamaica, or you can select a more secluded option if you're looking for a relaxing stay. Jamaica is known for its mountain views and art. Make sure you have time to check out the monuments while you're in the area.

What are some of the best holiday rentals that Jamaica has to offer?

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns: This holiday home rental outside of Jamaica is located on a river, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Jamaica?

With 42 Expedia holiday rentals, you're guaranteed to find just the right place for your Jamaica stay.

What can I see and do in Jamaica?

Cultural attractions include Hot Glass Works and Margie's Muse Handweaving & Gallery, whereas Green Mountain National Forest and Winhall River are a couple of picturesque spots to enjoy the outdoors. You’ll find favourite places to visit such as Stratton Mountain Resort and Mount Snow in the wider area.

What are holiday rentals like in Jamaica?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Jamaica. Holiday rentals offer extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for family gatherings.