Jamaica Holiday Rentals

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Check prices for these dates

Tonight
31 Oct - 1 Nov
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1 Nov - 2 Nov
This weekend
31 Oct - 2 Nov
Next weekend
7 Nov - 9 Nov

Holiday Rentals in Jamaica

Fridge, microwave, oven, stovetop
This house is a 4 bedroom(s), 2.5 bathrooms, located in Jamaica, VT.
This house is a 4 bedroom(s), 2.5 bathrooms, located in Jamaica, VT.
9.0 out of 10, Wonderful, (6)
"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 HK$2,844
HK$5,956 total
includes taxes & fees
2 Nov - 3 Nov
This house is a 4 bedroom(s), 2.5 bathrooms, located in Jamaica, VT.
Sauna
Wellness Getaway with a Personal Sauna, and Private River Beach!
Wellness Getaway with a Personal Sauna, and Private River Beach!
2.0 star property
10.0 out of 10, Exceptional, (1)
"The folks are SUPER and made me feel very welome"
United States
Mark
The price is HK$1,049
HK$1,975 total
includes taxes & fees
6 Nov - 7 Nov
Wellness Getaway with a Personal Sauna, and Private River Beach!
Property grounds
Lake Whitingham & Mount Snow Area Village Apartment
Lake Whitingham & Mount Snow Area Village Apartment
2.0 star property
10.0 out of 10, Exceptional, (1)
"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.
The price is HK$1,088
HK$2,367 total
includes taxes & fees
4 Nov - 5 Nov
Lake Whitingham & Mount Snow Area Village Apartment
Exterior
Mountain Chalet mins from Mt Snow Skiing/hiking
Mountain Chalet mins from Mt Snow Skiing/hiking
9.8 out of 10, Exceptional, (9)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is HK$910
HK$3,388 total
includes taxes & fees
2 Nov - 3 Nov
Mountain Chalet mins from Mt Snow Skiing/hiking
Property grounds
Family Friendly Hilltop House In Putney Vermont
Family Friendly Hilltop House In Putney Vermont
9.4 out of 10, Exceptional, (56)
"Gorgeous property. Super accommodating hosts. Would love to come back in the summer."
United States
Thomas F.
The price is HK$971
HK$1,984 total
includes taxes & fees
3 Nov - 4 Nov
Family Friendly Hilltop House In Putney Vermont
Exterior
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
9.6 out of 10, Exceptional, (165)
"We very much enjoyed our stay, check in was a breeze and we found the cabin to be a cozy retreat. We have been looking for a place that had a bed and bath on first floor to accommodate some mobility limitations and this home was perfect having a single step on the front porch. We look forward to booking another trip with this host "
United States
Jennifer
The price is HK$1,321
HK$2,767 total
includes taxes & fees
3 Nov - 4 Nov
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Private kitchen
Beautiful country cabin with hot tub and outdoor shower in Londonderry
Beautiful country cabin with hot tub and outdoor shower in Londonderry
2.0 star property
10.0 out of 10, Exceptional, (2)
"On a farm in the country…..stars blazing at night for hot tub. Cozy loft had amazing mattress and pillows! Our dog enjoyed the surrounding field. Beautiful! "
United States
Laurel
The price is HK$1,154
HK$2,805 total
includes taxes & fees
3 Nov - 4 Nov
Beautiful country cabin with hot tub and outdoor shower in Londonderry
Interior
Whimsical Room & Private Bathroom in Historic Inn
Whimsical Room & Private Bathroom in Historic Inn
8.8 out of 10, Excellent, (9)
"The room was really cozy and the community area was quaint and comfortable. "
United States
Bethany
The price is HK$769
HK$1,297 total
includes taxes & fees
2 Nov - 3 Nov
Whimsical Room & Private Bathroom in Historic Inn
Smart TV, fireplace, books
Private cabin: 7 mins to slopes, wood fireplace
Private cabin: 7 mins to slopes, wood fireplace
2.0 star property
9.6 out of 10, Exceptional, (5)
"Had a lovely stay here in mid-August. Despite the rain, played two rounds of golf at the beautiful resorts at Mt. Snow and Stratton. The house is nestled in the woods with a great view of the mountain ski trails. House is very spacious and the kitchen has everything you need! Our only issue was the lack of AC. Our bad luck to pick the most humid weekend of the summer, I guess, bc I know AC is rare in VT but maybe add more ceiling fans? Aside from that, we had a great time. "
United States
Suzanne H.
The price is HK$1,360
HK$4,355 total
includes taxes & fees
2 Nov - 3 Nov
Private cabin: 7 mins to slopes, wood fireplace
Smart TV, fireplace, ping pong
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.
10.0 out of 10, Exceptional, (5)
"We had an amazing stay at this ski house! The property was absolutely perfect for our group of 8. Spacious, clean, and beautifully designed with plenty of room for everyone. The location couldn’t have been better—just a short drive to the ski resort. Highly recommend this place for anyone looking for a comfortable and convenient ski getaway. We'll definitely be back!"
United States
katey
The price is HK$902
HK$3,381 total
includes taxes & fees
5 Nov - 6 Nov
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
Microwave, oven, stovetop
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
10.0 out of 10, Exceptional, (4)
"Impressively clean house! The owners were great to deal with and very responsive. Would certainly recommend to anyone traveling in the area."
United States
Kristen T.
The price is HK$1,321
HK$3,459 total
includes taxes & fees
2 Nov - 3 Nov
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
Fridge, microwave, oven, stovetop
Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.
Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.
9.8 out of 10, Exceptional, (73)
"This place was comfortable and just the right size foe my stay. Ownernwas responsive to communication before and during my stay. It's on the edge of Ludlow so close enough to walk into town for a.meal or the Sunday Farmer's Market. I would recommend taking the chair lift of Okemo Mountain then walking to the fire tower for a great view. If you walk away from the town, at the end of Mill Street there's a very refreshing swimming hole under the pedestrian bridge. You can.also find a bigger...
United States
Leigh B.
The price is HK$614
HK$1,782 total
includes taxes & fees
3 Nov - 4 Nov
Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.
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
9.0 out of 10, Wonderful, (72)
"It was a perfect location and had everything we needed for a great stay."
United States
Danna K.
The price is HK$583
HK$1,968 total
includes taxes & fees
2 Nov - 3 Nov
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Fridge, microwave, oven, stovetop
The Carol - 10 minutes to Okemo & Newly Renovated
The Carol - 10 minutes to Okemo & Newly Renovated
10.0 out of 10, Exceptional, (6)
"Perfect place for a weekend ski trip to Okemo. The host was very helpful!"
United States
Thomas G.
The Carol - 10 minutes to Okemo & Newly Renovated
Pool
Long Trail House at Stratton Mountain Resort
Long Trail House at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very good, (75)
"Nice, clean room in prime location"
United States
Kristin
The price is HK$2,549
HK$3,169 total
includes taxes & fees
6 Nov - 7 Nov
Long Trail House at Stratton Mountain Resort
Property grounds
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Cozy 3 bedroom condo 2.5 miles to Mount Snow
9.0 out of 10, Wonderful, (43)
"We loved the place. It was very homey and comfortable. My only suggestion would be to upgrade the towels and add a few more dish towels. "
United States
Kathy S.
The price is HK$699
HK$2,291 total
includes taxes & fees
10 Nov - 11 Nov
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Outdoor spa tub
The Mountain Escape!
The Mountain Escape!
9.6 out of 10, Exceptional, (20)
"Good spot for catching up with friends for the weekend. Hot tub was perfect and everything was comfortable."
United States
Ross P.
The price is HK$1,153
HK$4,718 total
includes taxes & fees
4 Nov - 5 Nov
The Mountain Escape!
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
10.0 out of 10, Exceptional, (8)
"Easy hand's off check in and great communication with the host. The cottage itself was lovely - my friends and I were in town for a wedding and it was the perfect accommodations! Would definitely stay here again! "
United States
Frances D.
The price is HK$1,590
HK$1,944 total
includes taxes & fees
2 Nov - 3 Nov
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
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
7.8 out of 10, Good, (52)
"Clean and convenient location to the village and base."
United States
Adam C.
The price is HK$552
HK$1,931 total
includes taxes & fees
4 Nov - 5 Nov
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Terrace/patio
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
10.0 out of 10, Exceptional, (14)
"Perfect weekend getaway "
United States
Seth G.
The price is HK$1,398
HK$3,371 total
includes taxes & fees
3 Nov - 4 Nov
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
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

Colonial Motel And Spa

Colonial Motel And Spa

10/10 Excellent
"YES, the room was SPOTLESS!!! An indoor Pool, Sauna & Continental Breakfast made this stay a PLUS!!! (Waffles, Toast, Coffee, Bagels, Cereal & Fresh Fruit). A definite choice for another visit!!!"
Barbara 1-night trip
Posted 11 hours ago
Colonial Motel And Spa

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!

Frequently asked questions

Can I find holiday rentals in Jamaica?

Yes, there are holiday rentals close to the most popular sights in Jamaica, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Jamaica has to offer?

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: This holiday home rental outside of Jamaica is located on a lake, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Jamaica?

With 38 Expedia holiday rentals, you're guaranteed 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 Dam are other places to visit while you're in town.

What are holiday rentals like in Jamaica?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Jamaica. Holiday rentals offer extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for family gatherings.