Jamaica Vacation Rentals

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Check prices for these dates

In two weeks
May 1 - May 3
In two months
Jun 12 - Jun 14
In three months
Jul 10 - Jul 12
In four months
Aug 7 - Aug 9

Our top choices for Jamaica vacation rentals

Exterior

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
8.8 out of 10, Excellent, (8 reviews)
"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 ￥52,351
￥116,105 total
includes taxes & fees
Apr 29 - Apr 30
Family-friendly A-Frame near Stratton, Bromley & Magic — hot tub retreat in the quiet, peaceful woods
Exterior

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (169 reviews)
"Very nice and clean cabin, not too far from small towns, decently supplied for expected conveniences, charming area - a small stream nearby provides a pleasant background noise. "
United States
Philip
The price is ￥26,969
￥58,634 total
includes taxes & fees
Apr 29 - Apr 30
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Exterior

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

Wellness Getaway with a Personal Sauna, and Private River Beach!
Newfane
10.0 out of 10, Exceptional, (3 reviews)
"Very welcoming and extremely helpful. Had a wonderful stay post ski day! Would definitely recommend and stay again. "
United States
Joseph P.
The price is ￥21,416
￥40,155 total
includes taxes & fees
May 13 - May 14
Wellness Getaway with a Personal Sauna, and Private River Beach!
Interior

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, (56 reviews)
"The place was very dirty. The linens were dirty, the pots/pans and all of the cooking utensils were dirty. There was a rubber band on the floor in bathroom that didn't belong to us.There was only 3 forks and a few spoons. Very little silverwear."
United States
Leigh-Ellen F.
The price is ￥8,408
￥46,558 total
includes taxes & fees
Apr 19 - Apr 20
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Property grounds

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (59 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is ￥22,559
￥43,923 total
includes taxes & fees
Apr 20 - Apr 21
Family Friendly Hilltop House In Putney Vermont
TV, books

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Walpole
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
The price is ￥31,806
￥38,984 total
includes taxes & fees
Apr 19 - Apr 20
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Interior

Beautiful country cabin with hot tub and outdoor shower in Londonderry

Beautiful country cabin with hot tub and outdoor shower in Londonderry
Londonderry
10.0 out of 10, Exceptional, (3 reviews)
"Stay is very cozy and rustic. Be prepared for house to be cold when you show up. Host is very responsive and accommodating."
United States
Michael D.
The price is ￥23,558
￥58,173 total
includes taxes & fees
Apr 20 - Apr 21
Beautiful country cabin with hot tub and outdoor shower in Londonderry
Property grounds

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, (79 reviews)
"Unit was as advertised. Clean and comfortable."
United States
Ralph D.
The price is ￥11,898
￥41,153 total
includes taxes & fees
Apr 22 - Apr 23
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Outdoor pool, a heated pool

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
9.4 out of 10, Exceptional, (23 reviews)
"Perfect spot for Mount Snow "
United States
Bobby
The price is ￥9,715
￥49,699 total
includes taxes & fees
Apr 19 - Apr 20
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Private kitchen

The Studio with a View. Bring your dog, too!

The Studio with a View. Bring your dog, too!
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"Great cozy little mountain cabin stay!! Well-appointed studio barn/cabin with scenic view and great proximity to skiing. Would stay again : )"
United States
James M.
The price is ￥20,465
￥41,932 total
includes taxes & fees
Apr 29 - Apr 30
The Studio with a View. Bring your dog, too!
Property grounds

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Clock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
"Great property, clean and close to the slope"
United States
tiliger01
The price is ￥7,773
￥35,354 total
includes taxes & fees
Apr 19 - Apr 20
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Property grounds

Lovely ski-in/out condo steps from ski lift with trails and amazing views

Lovely ski-in/out condo steps from ski lift with trails and amazing views
Stratton
8.4 out of 10, Very Good, (32 reviews)
"We loved staying at the townhome. It was a welcome place to stay while we traveled around, enjoying fall. It was very comfortable and the village amenities were great."
United States
John N.
The price is ￥11,263
￥48,364 total
includes taxes & fees
Apr 19 - Apr 20
Lovely ski-in/out condo steps from ski lift with trails and amazing views
TV

Ski-In/Out Condo with Mountain Views, and Washer/Dryer

Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Ludlow
9.6 out of 10, Exceptional, (18 reviews)
"Perfect spot to jump onto the mountain and ski. Two adults and 4 kids, and we had plenty of space for a long weekend."
United States
Allison T.
The price is ￥19,830
￥66,148 total
includes taxes & fees
Apr 19 - Apr 20
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Interior

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Cozy little spot that had everything we needed. Peaceful, quiet, and once the rain let up on our stay we walked out to the gorgeous little pond on the property. So serene. Catherine was great!"
United States
Erica H.
The price is ￥13,484
￥32,446 total
includes taxes & fees
Apr 30 - May 1
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
House (4 Bedrooms) | Interior

Outdoor Adventure Hub! Family Home in West Dover

Outdoor Adventure Hub! Family Home in West Dover
3.0 star property
West Dover
The price is ￥24,272
￥82,736 total
includes taxes & fees
Apr 19 - Apr 20
Outdoor Adventure Hub! Family Home in West Dover
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
7.8 out of 10, Good, (57 reviews)
"Location was great, pool, hot tubs and sauna were great"
United States
Lin M.
The price is ￥11,263
￥38,660 total
includes taxes & fees
Apr 22 - Apr 23
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Interior

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (85 reviews)
"We had a great stay at this home for a long weekend skiing at Okemo. "
United States
Lisa W.
The price is ￥17,847
￥48,293 total
includes taxes & fees
Apr 19 - Apr 20
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Property grounds

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Stratton
7.4 out of 10, Good, (21 reviews)
"A great weekend. The property was clean and comfortable."
United States
Joan P.
The price is ￥21,099
￥61,460 total
includes taxes & fees
Apr 19 - Apr 20
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Children's area

Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.6 out of 10, Exceptional, (12 reviews)
"The best stay ever!!! Very clean, great location, super cozy, all the amenities you would need. 5/5 stars, we will be coming back :)"
United States
Carolina I.
The price is ￥14,379
￥51,574 total
includes taxes & fees
Apr 19 - Apr 20
Cozy Bromley Retreat
Exterior

Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
9.8 out of 10, Exceptional, (10 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is ￥13,977
￥64,122 total
includes taxes & fees
Apr 19 - Apr 20
Chalet Mount Snow/Stratton 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

Latchis Hotel

Latchis Hotel

6/10 Okay
"There’s no sound proofing because it’s an old historic building. the exposed air ducts carry voices from hall and adjacent rooms.The suites are designed poorly. You have to walk through the master bedroom past the bed to get to the bathroom from the other bedroom. The whole place smells like burnt popcorn from the movie theater. And the front desk isn’t open at night. The sheets were clean. The shower was clean. The ceiling has exposed insulation. These are very outdated rooms. The windows are all pretty broken. One window had BB gun holes in it! Super convenient to downtown though."
Erin Lee 1-night trip
Posted 13 hours ago
Latchis Hotel

Find out more about Jamaica

Search for holiday rentals in Jamaica on Expedia! You can easily find your home rentals, villas, holiday apartments in Jamaica using one of the methods below:

  • View our selection of featured holiday rentals in Jamaica
  • Use the map to find apartments and other holiday homes in the Jamaica neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Jamaica while they last

Look no further and take a look at our great range of rental properties in Jamaica!

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Jamaica?

Yes, there are vacation rentals close to well known attractions in Jamaica, or you can select a more remote option if you'd like a relaxing place to 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 vacation home rentals that Jamaica has to offer?

Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna: Visitors like this Jamaica vacation home rental. It is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 11 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Jamaica?

With 40 Expedia vacation rentals, you're sure 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. Jamaica State Park and West River are other places to visit while you're in town.

What are vacation rentals like in Jamaica?

Vacation rentals are private properties you can stay in for a few days or a quick weekend in Jamaica. Vacation rentals feature extras like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from public hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for a small group gathering.