Jamaica Vacation Rentals

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Check prices for these dates

In two weeks
Mar 27 - Mar 29
In two months
May 8 - May 10
In three months
Jun 5 - Jun 7
In four months
Jul 3 - Jul 5

Our top choices for Jamaica vacation rentals

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.
$849 nightly
The price is $908
Mar 11 - Mar 12
Total with taxes and fees
New Stratton Ski Haus: A-Frame Hot Tub Sauna EV Privacy 1Gbps Manchester Okemo
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.
$682 nightly
The price is $722
Mar 31 - Apr 1
Total with taxes and fees
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, (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
$326 nightly
The price is $365
Mar 11 - Mar 12
Total with taxes and fees
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.
$223 nightly
The price is $250
Mar 18 - Mar 19
Total with taxes and fees
Wellness Getaway with a Personal Sauna, and Private River Beach!
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.
$220 nightly
The price is $238
Mar 11 - Mar 12
Total with taxes and fees
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
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.
$545 nightly
The price is $591
Mar 11 - Mar 12
Total with taxes and fees
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Interior

Cozy cabin in charming Londonderry

Cozy cabin in charming Londonderry
Londonderry
8.4 out of 10, Very Good, (5 reviews)
"Very cozy and quiet. "
United States
Eric H.
$245 nightly
The price is $276
Mar 11 - Mar 12
Total with taxes and fees
Cozy cabin in charming Londonderry
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.
$232 nightly
The price is $260
Mar 20 - Mar 21
Total with taxes and fees
The Studio with a View. Bring your dog, too!
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.
$244 nightly
The price is $273
Mar 17 - Mar 18
Total with taxes and fees
Family Friendly Hilltop House In Putney Vermont
Property grounds

Lake Whitingham & Mount Snow Area Village Apartment

Lake Whitingham & Mount Snow Area Village Apartment
Whitingham
10.0 out of 10, Exceptional, (1 review)
"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.
$274 nightly
The price is $307
Mar 11 - Mar 12
Total with taxes and fees
Lake Whitingham & Mount Snow Area Village Apartment
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.
$274 nightly
The price is $310
Mar 11 - Mar 12
Total with taxes and fees
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Exterior

Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna

Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
Stratton
$180 nightly
The price is $203
Mar 11 - Mar 12
Total with taxes and fees
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
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
$278 nightly
The price is $314
Mar 23 - Mar 24
Total with taxes and fees
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
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.
$356 nightly
The price is $402
Mar 11 - Mar 12
Total with taxes and fees
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Living area

Cozy Private Cabin in Andover - Fireplace & Hot tub

Cozy Private Cabin in Andover - Fireplace & Hot tub
Andover
$448 nightly
The price is $502
Mar 15 - Mar 16
Total with taxes and fees
Cozy Private Cabin in Andover - Fireplace & Hot tub
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, (78 reviews)
"Perfect location for a quick ski trip. "
United States
Michael D.
$248 nightly
The price is $280
Apr 7 - Apr 8
Total with taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
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.
$203 nightly
The price is $229
Mar 16 - Mar 17
Total with taxes and fees
Efficient condo near slopes with kitchenette & great location
Exterior

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Ludlow
9.0 out of 10, Wonderful, (25 reviews)
"Great rate for a place with all the basics!"
United States
Macgregor
$237 nightly
The price is $268
Mar 11 - Mar 12
Total with taxes and fees
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Interior

Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.

Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
Dover
10.0 out of 10, Exceptional, (12 reviews)
"We enjoyed our stay."
United States
Anonymous traveler
$507 nightly
The price is $573
Mar 11 - Mar 12
Total with taxes and fees
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
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.
$224 nightly
The price is $253
Apr 7 - Apr 8
Total with taxes and fees
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
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

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

4/10 Poor
"Front entrance floor was dirty; bedside table had trash in it. TV kept going out (excessively); no shower curtain (but quickly replaced by staff), no bathmat. And, shower screeched the entire time it was on. "
Sara 1-night trip
Posted 2 hours ago
Comfort Inn & Suites Brattleboro I-91

Find out more about Jamaica

Everything you need to know about Jamaica vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Jamaica vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Jamaica vacation 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 low season months. For more hustle and bustle, you may prefer to visit Jamaica in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $280 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Jamaica rentals

At Expedia, we put the best Jamaica vacation 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 vacation.

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.

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.