Jamaica Vacation Rentals

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Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

Our top choices for Jamaica vacation rentals

Exterior

Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.

Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.
Jamaica
8.8 out of 10, Excellent, (8 reviews)
"Beautiful home, we enjoyed our stay!"
United States
Luke B.
$691 nightly
The price is $732
May 10 - May 11
Total with taxes and fees
Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.
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)
"3rd year at this listing, absolutely love it. Close to okemo and mount snow. Host got back to me very quickly when reached out to. "
United States
Jake D.
$321 nightly
The price is $360
May 11 - May 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.
$257 nightly
The price is $288
May 28 - May 29
Total with taxes and fees
Wellness Getaway with a Personal Sauna, and Private River Beach!
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.
$265 nightly
The price is $297
May 11 - May 12
Total with taxes and fees
Family Friendly Hilltop House In Putney Vermont
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.
$230 nightly
The price is $259
May 8 - May 9
Total with taxes and fees
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
$289 nightly
The price is $327
May 10 - May 11
Total with taxes and fees
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)
"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.
$339 nightly
The price is $383
May 8 - May 9
Total with taxes and fees
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
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.
$267 nightly
The price is $290
May 11 - May 12
Total with taxes and fees
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
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)
"Location location location!"
United States
Britt H.
$369 nightly
The price is $417
May 8 - May 9
Total with taxes and fees
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
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, (58 reviews)
"Location was great, pool, hot tubs and sauna were great"
United States
Lin M.
$214 nightly
The price is $241
May 12 - May 13
Total with taxes and fees
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)
"Great proximity to mountain and Ludlow downtown area."
United States
Yasmine O.
$286 nightly
The price is $304
May 10 - May 11
Total with taxes and fees
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Smart TV, fireplace, stereo

LUXE Forest Retreat

LUXE Forest Retreat
Chester
$432 nightly
The price is $484
May 10 - May 11
Total with taxes and fees
LUXE Forest Retreat
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
$474 nightly
The price is $522
May 8 - May 9
Total with taxes and fees
Outdoor Adventure Hub! Family Home in West Dover
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.
$288 nightly
The price is $325
May 10 - May 11
Total with taxes and fees
Cozy Bromley Retreat
Property grounds

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
9.8 out of 10, Exceptional, (108 reviews)
"We enjoyed our stay, the house was lovely and close to everything in Ludlow and Okemo."
United States
Hannah M.
$285 nightly
The price is $303
May 11 - May 12
Total with taxes and fees
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Smart TV, fireplace, books

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (109 reviews)
"Convenient 2 BR space with comfy beds right in the heart of Ludlow. Would definitely stay there again."
United States
Andrew L.
$268 nightly
The price is $290
May 11 - May 12
Total with taxes and fees
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Interior

Stratton Woods · Secluded Vermont Cabin Retreat

Stratton Woods · Secluded Vermont Cabin Retreat
Wardsboro
9.4 out of 10, Exceptional, (3 reviews)
"Cabin was wonderful!Thank you,The Katz Family "
United States
kim k.
$342 nightly
The price is $347
May 11 - May 12
Total with taxes and fees
Stratton Woods · Secluded Vermont Cabin Retreat
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)
"Poor management company. Great lodge. "
United States
Billy W.
$344 nightly
The price is $389
May 8 - May 9
Total with taxes and fees
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
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

Econo Lodge Brattleboro South

Econo Lodge Brattleboro South

2/10 Terrible
"This place looks like crime scene #2. The rooms are clean, but they're also ragged as hell. Holes in the wall, lights that don't work. It's where you go when you don't have any other choices. If that's the case, you could do worse. But block the door with a chair or suitcase, because the chains are busted."
Constantine 2-night trip
Posted 18 hours ago
Econo Lodge Brattleboro South

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 $288 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?

Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!: You might want to consider this vacation home rental near Jamaica, which is located in the mountains and has a garden, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Jamaica?

With 39 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 Winhall River and Green Mountain National Forest are a couple of picturesque spots to enjoy the outdoors. Jamaica State Park and Ball Mountain Dam 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.