Jamaica Vacation Rentals

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Check prices for these dates

In two weeks
Mar 20 - Mar 22
In two months
May 1 - May 3
In three months
May 29 - May 31
In four months
Jun 26 - Jun 28

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 ￥52,067
￥113,871 total
includes taxes & fees
Mar 31 - Apr 1
Family-friendly A-Frame near Stratton, Bromley & Magic — hot tub retreat in the quiet, peaceful woods
Smart TV, fireplace, books, stereo

New Stratton Ski Haus: A-Frame Hot Tub Sauna EV Privacy 1Gbps Manchester Okemo

New Stratton Ski Haus: A-Frame Hot Tub Sauna EV Privacy 1Gbps Manchester Okemo
Jamaica
10.0 out of 10, Exceptional, (3 reviews)
"Couldn't be better! Outstanding! We had our family holiday ski trip from Dec 25-29th,2025. The amenities were second to none. The hot tub, sauna and fire pit made the winter warm! The house was clean comfortable and very cozy. The kitchen was extremely well appointed (sharp knives!). The staples available (coffee, tea, oil, spices etc.) were high quality and the best I've ever experienced in a short term rental. The beds and bedding were very comfortable! Most immortality the hosts were very...
United States
Laird N.
The price is ￥70,149
￥159,702 total
includes taxes & fees
Mar 5 - Mar 6
New Stratton Ski Haus: A-Frame Hot Tub Sauna EV Privacy 1Gbps Manchester Okemo
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
9.2 out of 10, Wonderful, (22 reviews)
"Highly recommend clean beautiful stay!"
United States
Douglas D.
The price is ￥9,682
￥48,795 total
includes taxes & fees
Mar 23 - Mar 24
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
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)
"Irish Bar nearby was a plus on St. Patrick’s Day !"
United States
Warren
The price is ￥12,465
￥51,003 total
includes taxes & fees
Mar 23 - Mar 24
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
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 ￥19,659
￥40,337 total
includes taxes & fees
Mar 20 - Mar 21
The Studio with a View. Bring your dog, too!
Golf

Well-appointed studio right downtown - less than a mile to Okemo Mountain

Well-appointed studio right downtown - less than a mile to Okemo Mountain
Ludlow
8.6 out of 10, Excellent, (12 reviews)
"Clean with everything we needed for a few nights stay."
United States
Sandra S.
The price is ￥16,725
￥49,190 total
includes taxes & fees
Mar 5 - Mar 6
Well-appointed studio right downtown - less than a mile to Okemo Mountain
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
7.6 out of 10, Good, (54 reviews)
"Location was great, pool, hot tubs and sauna were great"
United States
Lin M.
The price is ￥15,570
￥44,640 total
includes taxes & fees
Apr 1 - Apr 2
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
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, (31 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 ￥16,199
￥53,791 total
includes taxes & fees
Mar 23 - Mar 24
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Children's area

Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.4 out of 10, Exceptional, (10 reviews)
"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 ￥16,739
￥54,534 total
includes taxes & fees
Apr 1 - Apr 2
Cozy Bromley Retreat
Beach

Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow
West Dover
9.2 out of 10, Wonderful, (50 reviews)
"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.
The price is ￥15,727
￥47,450 total
includes taxes & fees
Mar 23 - Mar 24
Cozy 3 bedroom condo 2.5 miles to Mount Snow
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, (28 reviews)
"Overall very clean and nice. Needs some updating like more spoons, only 2, bigger coffee cups. And a new coffee table that is very worn. "
United States
David A.
The price is ￥17,356
￥48,622 total
includes taxes & fees
Mar 11 - Mar 12
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
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 ￥21,231
￥39,279 total
includes taxes & fees
Mar 19 - Mar 20
Wellness Getaway with a Personal Sauna, and Private River Beach!
Golf

Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location
Ludlow
8.6 out of 10, Excellent, (32 reviews)
"Nice place close to mountain easy in easy out"
United States
Aaron B.
The price is ￥16,882
￥36,313 total
includes taxes & fees
Mar 10 - Mar 11
Efficient condo near slopes with kitchenette & great location
Living area

Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham

Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
Whitingham
The price is ￥57,246
￥101,458 total
includes taxes & fees
Mar 5 - Mar 6
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
Lobby

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
8.6 out of 10, Excellent, (35 reviews)
"Great place with great amenities! "
United States
Rachel R.
The price is ￥15,305
￥54,599 total
includes taxes & fees
Mar 29 - Mar 30
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
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, (167 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 ￥26,736
￥56,190 total
includes taxes & fees
Mar 12 - Mar 13
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Exterior

2nd-floor downtown Ludlow studio condo with kitchenette, streaming

2nd-floor downtown Ludlow studio condo with kitchenette, streaming
Ludlow
8.6 out of 10, Excellent, (4 reviews)
"Great location and convenient to all local businesses. I enjoyed it very much. Would stay here anytime and plan to again. "
United States
Kevin C.
The price is ￥17,987
￥42,855 total
includes taxes & fees
Apr 1 - Apr 2
2nd-floor downtown Ludlow studio condo with kitchenette, streaming
Terrace/patio

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Walpole
10.0 out of 10, Exceptional, (50 reviews)
"We had a very lovely stay. "
United States
mary c.
The price is ￥44,589
￥93,231 total
includes taxes & fees
Mar 9 - Mar 10
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
House (5 Bedrooms) | Interior

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
Ludlow
The price is ￥173,154
￥269,301 total
includes taxes & fees
Mar 5 - Mar 6
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
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 ￥24,771
￥46,829 total
includes taxes & fees
Apr 1 - Apr 2
Family Friendly Hilltop House In Putney Vermont
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

The Putney Inn

The Putney Inn

10/10 Excellent
"Our second stay here, just as good at the first. Friendly, cozy even in winter, plentiful parking, conveniently right off I-95. Breakfast is included and isn’t fancy but is satisfying. "
Catherine 1-night trip
Posted 2 days ago
The Putney Inn

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?

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms: Visitors like this Jamaica vacation home rental. It is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 12 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 garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Jamaica?

With 43 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 Ball Mountain State Park 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.