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Vacation Homes in Jamaica

Our top choices for Jamaica vacation homes

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 ¥56,815
¥116,876 total
includes taxes & fees
Aug 24 - Aug 25
This house is a 4 bedroom(s), 2.5 bathrooms, located in Jamaica, VT.

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 ¥15,826
¥29,917 total
includes taxes & fees
Sep 3 - Sep 4
Charming 1-bedroom condo in delightful Dover

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 ¥17,089
¥64,550 total
includes taxes & fees
Aug 24 - Aug 25
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

7.8 out of 10, Good, (50)
"Great condo in great location. Easy walk to restaurants and lifts."
The price is ¥10,502
¥36,758 total
includes taxes & fees
Aug 24 - Aug 25
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Cozy motel suite in charming Woodford with WiFi, AC

The price is ¥14,791
¥19,879 total
includes taxes & fees
Sep 5 - Sep 6
Cozy motel suite in charming Woodford with WiFi, AC

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 ¥22,197
¥42,421 total
includes taxes & fees
Sep 6 - Sep 7
Family Friendly Hilltop House In Putney Vermont

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 ¥26,965
¥80,278 total
includes taxes & fees
Aug 25 - Aug 26
Ski in Ski out Condo! Pool access

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 ¥23,296
¥65,604 total
includes taxes & fees
Aug 20 - Aug 21
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

10.0 out of 10, Exceptional, (2)
"as advertised."
The price is ¥56,945
¥101,052 total
includes taxes & fees
Sep 10 - Sep 11
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

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 ¥26,358
¥47,579 total
includes taxes & fees
Sep 2 - Sep 3
The Carol - 10 minutes to Okemo & Newly Renovated- NEW SAUNA SEPT 2025!

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 ¥40,477
¥52,392 total
includes taxes & fees
Sep 1 - Sep 2
Brook Bound Inn - Main Lodge - Deluxe King w/ Pullout Couch - Room 203

Alpine 5, cozy Vermont retreat

The price is ¥15,455
¥22,756 total
includes taxes & fees
Aug 24 - Aug 25
Alpine 5, cozy Vermont retreat

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 ¥19,228
¥53,484 total
includes taxes & fees
Aug 21 - Aug 22
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!

10.0 out of 10, Exceptional, (14)
"We loved the house, the deck and the property amenities."
The price is ¥28,990
¥79,932 total
includes taxes & fees
Aug 26 - Aug 27
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

2.0 star property
The price is ¥37,357
¥72,983 total
includes taxes & fees
Sep 1 - Sep 2
Enjoy this authentic and cozy VT Barn with Brand New Hot 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 ¥18,057
¥84,084 total
includes taxes & fees
Sep 10 - Sep 11
Mountain Oasis - Hot Tub, Sauna, Fire Pit, & MORE!

Modern Chic Cabin near Mount Snow

The price is ¥22,608
¥71,952 total
includes taxes & fees
Sep 1 - Sep 2
Modern Chic Cabin near Mount Snow

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

2.0 star property
The price is ¥184,888
¥283,634 total
includes taxes & fees
Aug 24 - Aug 25
8mins Mount Snow - NEW Cabin 3600SF - Game Room - 20%OFF

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 ¥25,567
¥44,131 total
includes taxes & fees
Sep 1 - Sep 2
Charming Cavendish Guesthouse NEW SAUNA SEPT 2025!

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

The price is ¥28,665
¥93,470 total
includes taxes & fees
Aug 20 - Aug 21
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