A road flanked by dense bamboo groves.

Jamaica Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Jamaica vacation rentals

Room

1. Cozy A-Frame Cabin with Hot Tub & Sauna near Stratton Mountain, Vermont

Cozy A-Frame Cabin with Hot Tub & Sauna near Stratton Mountain, Vermont
Jamaica
$993 nightly
The price is $1,122
Nov 3 - Nov 4
Total with taxes and fees
Cozy A-Frame Cabin with Hot Tub & Sauna near Stratton Mountain, Vermont
A spacious living room with a high ceiling, wooden beams, a large sofa, a dining table, and a view of the outdoors through large windows.

2. Vermont A-Frame | Sleeps10, Hot Tub, Sauna, EV, AC

Vermont A-Frame | Sleeps10, Hot Tub, Sauna, EV, AC
Jamaica
10.0 out of 10, Exceptional, (3 reviews)
"Great peaceful stay. Hosts were always in communication with us. Close to Stratton. Hot tube & sauna were a great top off to a day of skiing. "
United States
fran g.
$902 nightly
The price is $1,019
Nov 3 - Nov 4
Total with taxes and fees
Vermont A-Frame | Sleeps10, Hot Tub, Sauna, EV, AC
A lodge with a large fireplace, a covered porch, and a staircase leading to the upper level.

3. 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.
$512 nightly
The price is $553
Oct 7 - Oct 8
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.
A swimming pool with a stone border, surrounded by a snow-covered landscape and a wooden fence.

4. Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort
3.0 star property
Stratton
8.6 out of 10, Excellent, (84 reviews)
"Nice place and great location!!!"
United States
William
$391 nightly
The price is $441
Oct 7 - Oct 8
Total with taxes and fees
Long Trail House at Stratton Mountain Resort
A building with a sign reading 'Fire Tower Restaurant & Tavern.'

5. 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
$199 nightly
The price is $224
Oct 7 - Oct 8
Total with taxes and fees
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

6. 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
$227 nightly
The price is $256
Oct 7 - Oct 8
Total with taxes and fees
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
A wooden cabin interior with a dining area, staircase, and a chandelier.

7. The Perfect Vermont Getaway! 3 bedroom, Fireplace, indoor Pool & Mountain Charm

The Perfect Vermont Getaway! 3 bedroom, Fireplace, indoor Pool & Mountain Charm
Wardsboro
10.0 out of 10, Exceptional, (2 reviews)
"Everything was wonderful and perfect for our family. Super clean and great Vermont experience"
United States
Lisa B.
$482 nightly
The price is $545
Oct 21 - Oct 22
Total with taxes and fees
The Perfect Vermont Getaway! 3 bedroom, Fireplace, indoor Pool & Mountain Charm
A living room with a television, sofa, and coffee table.

8. Long Trail House South Wing 2B2B Condo

Long Trail House South Wing 2B2B Condo
Stratton
10.0 out of 10, Exceptional, (5 reviews)
"Very clean 2br 2ba condo in excellent location. Host provided detailed important information that helped us find property and how to access unit. I would definitely recommend staying here."
United States
Eileen R.
$408 nightly
The price is $461
Oct 13 - Oct 14
Total with taxes and fees
Long Trail House South Wing 2B2B Condo
A modern kitchen with dark cabinetry, stainless steel appliances, and a bar area with stools.

9. Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub

Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
Stratton Mountain
10.0 out of 10, Exceptional, (36 reviews)
"Great space, great location!"
United States
Jason S.
$471 nightly
The price is $532
Oct 27 - Oct 28
Total with taxes and fees
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
A wooden deck with a black Adirondack chair and a small table, surrounded by trees.

10. Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Wardsboro
10.0 out of 10, Exceptional, (20 reviews)
"Cute place, very pet-friendly."
United States
Jeff H.
$389 nightly
The price is $440
Nov 2 - Nov 3
Total with taxes and fees
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
A modern two-story house with a front porch, a staircase, and a driveway.

11. Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!

Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Jamaica
9.6 out of 10, Exceptional, (30 reviews)
"House was perfect for a guys trip for skiing. Just as expected. Would stay again. "
United States
Michael A.
$862 nightly
The price is $974
Oct 14 - Oct 15
Total with taxes and fees
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
A spacious living room with a stone fireplace, wooden beams, and a large sofa.

12. Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester

Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
Londonderry
9.6 out of 10, Exceptional, (25 reviews)
"Super attentive and accommodating host! It was a perfect cozy getaway on a frigid weekend, and the fireplace and hot tub were just the ticket. "
United States
Meghan R.
$574 nightly
The price is $648
Nov 2 - Nov 3
Total with taxes and fees
Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
A multi-story building with a stone facade, a central courtyard with a hot tub, and a stone pathway.

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

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Stratton
8.0 out of 10, Very good, (1 review)
$360 nightly
The price is $406
Oct 7 - Oct 8
Total with taxes and fees
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
A living room with a sofa, a television, a fireplace, and a dining area with chairs and a table.

14. 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, (36 reviews)
"I have stayed in this condo a few times now, and for my needs it is a great value; affordable, comfortable and ideal location. "
United States
eric m.
$278 nightly
The price is $314
Oct 7 - Oct 8
Total with taxes and fees
Lovely ski-in/out condo steps from ski lift with trails and amazing views
A hallway with a bench, a wall-mounted towel rack, and a door leading to an outdoor area.

15. The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!

The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
Wardsboro
10.0 out of 10, Exceptional, (12 reviews)
"Loved this place so much! Adorable spot, quaint but has everything you need. Loved the luxury details. "
United States
Carly L.
$434 nightly
The price is $490
Nov 2 - Nov 3
Total with taxes and fees
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
A spacious living area with a gray sofa, a coffee table, and a kitchen area with a bar counter and stools.

16. Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!

Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!
Londonderry
10.0 out of 10, Exceptional, (11 reviews)
"Great location, well-designed house, and a beautiful view."
United States
Marcel P.
$749 nightly
The price is $846
Oct 19 - Oct 20
Total with taxes and fees
Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!
A living room with a brick fireplace, a sofa, a chair, and a coffee table.

17. Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
Winhall
10.0 out of 10, Exceptional, (15 reviews)
"Clean, lots of room, easy access to Stratton, responsive host."
United States
Mark H.
$811 nightly
The price is $916
Oct 25 - Oct 26
Total with taxes and fees
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
A modern living room with a fireplace, a large sofa set, and a view through the glass doors.

18. New! Vermont Getaway! Stratton - close to skiing!

New! Vermont Getaway! Stratton - close to skiing!
Winhall
10.0 out of 10, Exceptional, (1 review)
"The place was perfect for us! Easy stay. Very clean and the wood burning fireplace was great. Would def recommend!"
United States
Carolyn K.
$518 nightly
The price is $526
Nov 3 - Nov 4
Total with taxes and fees
New! Vermont Getaway! Stratton - close to skiing!
A wooden cabin with a patio area featuring Adirondack chairs, a hot tub, and a fire pit.

19. Luxe Chalet - Leaf Peeping, Near Mt Snow and Stratton Mountain w/Hot Tub, Sauna

Luxe Chalet - Leaf Peeping, Near Mt Snow and Stratton Mountain w/Hot Tub, Sauna
Stratton
10.0 out of 10, Exceptional, (7 reviews)
"Everything about our stay was top notch. Highly recommend and I will book this house again. "
United States
samantha b.
$679 nightly
The price is $767
Oct 12 - Oct 13
Total with taxes and fees
Luxe Chalet - Leaf Peeping, Near Mt Snow and Stratton Mountain w/Hot Tub, Sauna
A cozy room with wooden walls, two green upholstered chairs with plaid cushions, a small round wooden table with a cup and a book, and a framed map of Vermont on the wall.

20. The MountainTop | Stratton & Mt Snow | Fire Pit

The MountainTop | Stratton & Mt Snow | Fire Pit
Stratton
10.0 out of 10, Exceptional, (10 reviews)
"Lovely place to stay. The stars truly are stunning. "
United States
Brenna G.
$485 nightly
The price is $581
Oct 12 - Oct 13
Total with taxes and fees
The MountainTop | Stratton & Mt Snow | Fire Pit
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

Brittany Motel

Brittany Motel

10/10 Excellent
"clean room, good snacks, and beautiful location."
Mary 1-night trip
Posted 12 hours ago
Brittany Motel

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 $224 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?

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: 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 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Jamaica?

With 44 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.