Holiday Homes in Jamaica

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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Holiday Homes in Jamaica and around

This house is a 4 bedroom(s), 2.5 bathrooms, located in Jamaica, VT.
Fridge, microwave, oven, stovetop

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 !"
The price is €682
includes taxes & fees
1 Sept - 2 Sept
This house is a 4 bedroom(s), 2.5 bathrooms, located in Jamaica, VT.
Charming 1-bedroom condo in delightful Dover
Fridge, microwave, oven, stovetop

Charming 1-bedroom condo in delightful Dover

10.0 out of 10, Exceptional, (1)
"The place was nice. It was clean, lots of supplies were provided, and it was in a great location. The host contacted me the day before, letting me know that the wifi was out, and the technician was unavailable until the next week. I was appreciative of the heads up. Unfortunately, the TV was unusable without wifi, no option to watch local channels. Cellular (Verizon) data was non-existent throughout the majority of daytime hours. Despite this smallish issue, I would stay here again! "
The price is €178
includes taxes & fees
3 Sept - 4 Sept
Charming 1-bedroom condo in delightful Dover
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
Smart TV, fireplace, ping pong

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

10.0 out of 10, Exceptional, (4)
"Great location to Mt Snow and its surroundings. Easy, pleasant and accommodating communications with the host. Comfortable accommodations. "
The price is €384
includes taxes & fees
24 Aug - 25 Aug
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Interior

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

7.8 out of 10, Good, (50)
"Great condo in great location. Easy walk to restaurants and lifts."
The price is €218
includes taxes & fees
24 Aug - 25 Aug
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Cozy motel suite in charming Woodford with WiFi, AC
Interior

Cozy motel suite in charming Woodford with WiFi, AC

Cozy motel suite in charming Woodford with WiFi, AC
Family Friendly Hilltop House In Putney Vermont
Property grounds

Family Friendly Hilltop House In Putney Vermont

9.4 out of 10, Exceptional, (56)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
The price is €251
includes taxes & fees
6 Sept - 7 Sept
Family Friendly Hilltop House In Putney Vermont
Ski in Ski out Condo! Pool access
Terrace/patio

Ski in Ski out Condo! Pool access

9.0 out of 10, Wonderful, (2)
"Great location with plenty of space for the whole family. Highly recommend!"
The price is €498
includes taxes & fees
24 Aug - 25 Aug
Ski in Ski out Condo! Pool access
Mtn View & Hot Tub-Peaceful Property w/ stream-mins to Hiking, Biking, Swimming
Fridge, microwave, oven, stovetop

Mtn View & Hot Tub-Peaceful Property w/ stream-mins to Hiking, Biking, Swimming

9.0 out of 10, Wonderful, (2)
"Our family had the best time staying here. The home was spacious and gave our two young children plenty of room to roam and explore. It was also close enough to the main road where everything was accessible but also isolated enough where you feel like you're getting away. Erin was great about answering any questions and making sure our stay was comfortable. We'd definitely return here!"
The price is €396
includes taxes & fees
1 Sept - 2 Sept
Mtn View & Hot Tub-Peaceful Property w/ stream-mins to Hiking, Biking, Swimming
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
3 bedrooms, iron/ironing board, WiFi, bed sheets

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

10.0 out of 10, Exceptional, (2)
"as advertised."
The price is €590
includes taxes & fees
16 Sept - 17 Sept
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
The Carol - 10 minutes to Okemo & Newly Renovated- NEW SAUNA SEPT 2025!
Fridge, microwave, oven, stovetop

The Carol - 10 minutes to Okemo & Newly Renovated- NEW SAUNA SEPT 2025!

10.0 out of 10, Exceptional, (6)
"Check in and check out were incredibly easy, house decor was eclectic upscale, beds were super comfortable. Thank you Chris! Would definitely stay here again"
The price is €282
includes taxes & fees
2 Sept - 3 Sept
The Carol - 10 minutes to Okemo & Newly Renovated- NEW SAUNA SEPT 2025!
Brook Bound Inn - Main Lodge - Deluxe King w/ Pullout Couch - Room 203
Interior

Brook Bound Inn - Main Lodge - Deluxe King w/ Pullout Couch - Room 203

10.0 out of 10, Exceptional, (1)
"We stayed here for one night to ski at Mount Snow and it was amazing! Very comfortable, cozy, well kept, clean with well stocked kitchen. It was perfect for our purpose and would definitely come back!! "
The price is €313
includes taxes & fees
20 Aug - 21 Aug
Brook Bound Inn - Main Lodge - Deluxe King w/ Pullout Couch - Room 203
Alpine 5, cozy Vermont retreat
1 bedroom, desk, iron/ironing board, WiFi

Alpine 5, cozy Vermont retreat

Alpine 5, cozy Vermont retreat
Okemo's Back Room - in the heart of the village on the shuttle route!
Interior

Okemo's Back Room - in the heart of the village on the shuttle route!

9.6 out of 10, Exceptional, (14)
"Perfect location. Charming place to stay. Very clean. Great view of the creek."
The price is €317
includes taxes & fees
21 Aug - 22 Aug
Okemo's Back Room - in the heart of the village on the shuttle route!
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Smart TV, fireplace, video games, offices

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

10.0 out of 10, Exceptional, (14)
"We loved the house, the deck and the property amenities."
The price is €475
includes taxes & fees
26 Aug - 27 Aug
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
2 bedrooms, WiFi, bed sheets

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

2.0 star property
The price is €434
includes taxes & fees
1 Sept - 2 Sept
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Mountain Oasis - Hot Tub, Sauna, Fire Pit, & MORE!
Outdoor spa tub

Mountain Oasis - Hot Tub, Sauna, Fire Pit, & MORE!

9.8 out of 10, Exceptional, (26)
"Amazing stay. Perfect weekend friend getaway"
The price is €504
includes taxes & fees
8 Sept - 9 Sept
Mountain Oasis - Hot Tub, Sauna, Fire Pit, & MORE!
Modern Chic Cabin near Mount Snow
Terrace/patio

Modern Chic Cabin near Mount Snow

The price is €450
includes taxes & fees
30 Aug - 31 Aug
Modern Chic Cabin near Mount Snow
8mins Mount Snow - NEW Cabin 3600SF - Game Room - 20%OFF
Fridge, microwave, oven, stovetop

8mins Mount Snow - NEW Cabin 3600SF - Game Room - 20%OFF

2.0 star property
8mins Mount Snow - NEW Cabin 3600SF - Game Room - 20%OFF
Charming Cavendish Guesthouse NEW SAUNA SEPT 2025!
Interior

Charming Cavendish Guesthouse NEW SAUNA SEPT 2025!

9.8 out of 10, Exceptional, (6)
"Very cozy and had all the essentials we needed for our trip! Check in and check out were easy, and it was perfect for our winter trip. It's a short drive to Okemo, which is super convenient - would definitely stay here again!"
The price is €263
includes taxes & fees
1 Sept - 2 Sept
Charming Cavendish Guesthouse NEW SAUNA SEPT 2025!
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Interior

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
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

10/10 Excellent
"Really good staff! "
Seb 1-night trip
Posted 2 days ago
Comfort Inn & Suites Brattleboro I-91