We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation Rentals in Jamaica, VT and nearby

Payment Protection
Use a credit card to book with our Peace of Mind Protection.Learn more
Find a rental
Price per night
Min
Max
Bedrooms
Any
Amenities
Select
More filters
All 20 Rentals in the Jamaica Area
loading...
From
$250
Per Night
View Details
1 / 23
Payment Protection
Jamaica
4 Bedrooms, 3 Bathrooms, Sleeps 9
Details Make Inquiry
From
$300
Per Night
View Details
1 / 29
Payment Protection
Jamaica
3 Bedrooms, 3 Bathrooms, Sleeps 10
Booking
Details Make Inquiry
From
$300
Per Night
View Details
1 / 11
Payment Protection
Jamaica
4 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Make Inquiry
From
$180
Per Night
View Details
1 / 12
Payment Protection
Jamaica
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Details Make Inquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Fireplace
  • Internet Access
  • Mountain Views
  • Safe
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Wonderful 2-story log cabin with 3 bedrooms, 2 baths and hardwood floors throughout. The most prominent feature of the house is the large floor to ceiling fireplace that is perfect after a long day of skiing. Home has full internet access, with Direct TV and large flat screen TV. Has a large... View all property information
Make Inquiry

The following rentals are within 5 miles of Jamaica, Vermont.

From
$450
Per Night
View Details
1 / 6
Payment Protection
Stratton Mountain
3 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
Details Make Inquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Safe
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
World Class Skiing in the winter. Tennis and swimming on the premises in the Summer. Hike the Appalachian and Long Trails. Harriman Reservoir for boating/swimming and Marlboro Music for concerts within 20 miles. Manchester, VT is nearby for shopping. A wonderful vacation retreat all year.... View all property information
Make Inquiry
From
$300
Per Night
View Details
1 / 9
Payment Protection
Bondville
3 Bedrooms, 3 Bathrooms, Sleeps 10
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Completely remodeled in 2013, this end unit is one of Piper Ridge's most private on a dead end road with only one other neighbor. The townhouse features two king beds in the master and junior suite each with their own bathrooms. The upstairs rooms has two twins and an adjoining 'loft' area with a... View all property information
Make Inquiry
From
$175
Per Night
View Details
1 / 19
Payment Protection
West Wardsboro
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Secluded 2 level chalet in Scandia Village off Stratton-Arlington Rd. about 7' to Mt. Snow and 20' to Stratton Mountain . ski area. West Wardsboro Market nearby, and within walking distance.... Dover Vt. about 7 miles south on Rt. 100. Wilmington, Vt. about 25' ride with many restaurants... View all property information
Make Inquiry
5 of 5 stars Reviewed January 14, 2015
We rented from Pat and Marco for a stay around Christmas '14 and was very happy with the cabin. It's just what we wanted - simple, charming and no frills. All that and Pat was...
See all reviews
From
$3,000
Per Month
View Details
1 / 15
Payment Protection
Stratton Mountain
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Mountain Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Located less than 1 mile from quaint Stratton Mountain Village. Daily/weekend shuttle service to the slopes. One of the most popular Condo developments on the mountain. Decorated in custom adirondack style furniture. Gas fireplace. All new appliances. King size master bed. Bunk beds and queen... View all property information
Make Inquiry
From
$125
Per Night
View Details
1 / 4
Payment Protection
Wardsboro
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Make Inquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Mountain Views
  • Private Fishing...
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
FLIPKEY SUCKS FLIPKEY SUCKS FLIPKEY SUCKS FLIPKEY SUCKS FLIPKEY SUCKS FLIPKEY SUCKS FLIPKEY SUCKS FLIPKEY SUCKS FLIPKEY SUCKS FLIPKEY SUCKS FLIPKEY SUCKS FLIPKEY SUCKSFLIPKEY SUCKS FLIPKEY SUCKS FLIPKEY SUCKS FLIPKEY SUCKS FLIPKEY SUCKS v FLIPKEY SUCKS FLIPKEY SUCKS FLIPKEY SUCKS FLIPKEY SUCKS... View all property information
Make Inquiry
From
$75
Per Night
View Details
1 / 5
Payment Protection
Bondville
3 Bedrooms, 2 Bathrooms, Sleeps 7
Booking
Details Make Inquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
In the woods country home. Although I live here the guest rooms in my house are in a seperate area. You will have use of the kitchen and hot tub which are shared with me. Close to Stratton Mountain, Manchester Vt and much more. I will give you any information you want about things to do in... View all property information
Make Inquiry
Get the List
From
$750
Per Night
View Details
1 / 28
Payment Protection
Bondville
6 Bedrooms, 4 Bathrooms, Sleeps 16
Details Make Inquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Mountain Views
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Located in Stratton's exclusive High Meadow neighborhood, this luxury home boasts spacious accommodations with all the amenities. Come relax and enjoy mountain views, Jacuzzi tubs, a large family room with fireplace, a recreation room with pool table, 3-season porch, barbecues on the large outdoor... View all property information
Make Inquiry
From
$250
Per Night
View Details
1 / 29
Payment Protection
Stratton Mountain
3 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
Details Reviews (3) Make Inquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Fireplace
  • Gym
  • Internet Access
  • Mountain Views
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
A five minute drive from Bromley mountain, this condo is surrounded by everything that makes Vermont such a beautiful and natural state. For winter goers, you'll have your choice of three mountains within a 30 minute drive. For summer and fall goers, you'll have the opportunity to truly experience... View all property information
Make Inquiry
From
$190
Per Night
View Details
1 / 15
Payment Protection
West Wardsboro
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Dryer
  • Grill
  • Internet Access
  • Safe
  • Washer
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Our spacious 1,000sq ft cottage is perfect for a family of 4 or as a romantic getaway for two. 10 min to Mt. Snow and 15 min to Stratton for sport enthusiasts. Easy access on Rt. 100. Fenced in yard for dogs. Brookside deck for grillin' and chillin' * 10-15 minutes to Mt. Snow(depending on... View all property information
Make Inquiry
From
$550
Per Night
View Details
1 / 6
Payment Protection
Stratton Mountain
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (2) Make Inquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Gym
  • Internet Access
  • Mountain Views
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Enjoy the crisp, clean air of Vermont where cool winter nights or warm summer days will relax you. Our condominium sleeps 8, has a magnificent, sunny 30 mile panoramic view of Stratton and Magic Mountains and was recently renovated with the kitchen completely updated. The slopes of Bromley... View all property information
Make Inquiry
From
$300
Per Night
View Details
1 / 11
Payment Protection
West Wardsboro
7 Bedrooms, 3 Bathrooms, Sleeps 16
Booking
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Fireplace
  • Grill
  • Mountain Views
  • Safe
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Beautiful 7 Bedroom home... just 5 miles from Mount Snow and 7 miles to Stratton's Sun Bowl!! We are located in West Wardsboro (on Rt. 100). Manchester is only 45 minutes away. Great outlet shopping and restaurants in Manchester. • The home is spotlessly clean and a great place to enjoy with... View all property information
Make Inquiry
From
$109
Per Night
View Details
1 / 26
Stratton Mountain
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
On St. augustine Beach, relax and enjoy this Oceanfront condo with a beautiful view from the balcony, living room, dining room, kitchen and master bedroom. This fully furnished townhouse style, two bedroom, 2 & 1/2 bath unit has cable TV & a full size washer/dryer. Enjoy the very large, sparkling... View all property information
Make Inquiry
5 of 5 stars Reviewed December 2, 2014
The condo was perfect for our trip. Traveled with my wife, two teenage daughters and my mother. The unit was very clean and had everything you need for your stay. Publix and Winn...
See all reviews
From
$429
Per Night
View Details
1 / 23
Stratton Mountain
4 Bedrooms, 4 Bathrooms, Sleeps 10
Details Reviews (1) Make Inquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Weekly and Monthly rentals preferred. Minimun rental rate is $2,000 even for one night! See rate schedule to determine rental amount for the time period you seek. Maximun number of people in party is 10! Minimun advanced scheduleing for rental is 12 to 15 day prior to allow for financial... View all property information
Make Inquiry
5 of 5 stars Reviewed January 24, 2015
Beautiful house, very spacious. Nice for familly with kids. Highly recommanded. Only slight issue we had was that the access road was stip and very icy. Quite difficult to get to...
See all reviews
From
$110
Per Night
View Details
1 / 24
Stratton Mountain
4 Bedrooms, 5 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Water's Edge is located in South Londonderry along the West River on a quiet country road. In the warmer months, enjoy biking or strolling or jogging through the Vermont woods along the West River Trail, which starts at the end of our road. Recently added, a 46' flat screen wall mount tv! PayPal... View all property information
Make Inquiry
From
$450
Per Night
View Details
1 / 10
Bondville
4 Bedrooms, 3 Bathrooms, Sleeps 11
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Calender May NOT up to DATE please call or email PLEASE SCROLL DOWN TO SEE RATES and THERE IS A MAP BUTTON ABOVE Please check rates 5 nights min New Years and Presidents week 4 BR Mins from the mountain Up: MBR King Sleigh w/Pvt Bath Down: BR w/Queen, BR w/Queen, BR w/2 bunks, pull out couch... View all property information
Make Inquiry
From
$95
Per Night
View Details
1 / 12
Stratton Mountain
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Enjoy all Stratton has to offer from this southern Vermont vacation home rental, nestled in the mountains in South Londonderry, less than a 15 minute drive away to the base of the slopes. Located closest to Stratton Mountain, the home is also just a short drive to Bromley and Magic Mountains.... View all property information
Make Inquiry
Go to map view
Book Online(15)
Use filters to find the best results!

Suitability

  • Wheelchair access (2)
  • Elder access (7)
  • Suitable for children (0)
  • Pet friendly (8)
  • Smoking allowed (0)

Amenities

  • Other outdoor space (19)
  • Washer/Dryer (19)
  • Parking (18)
  • Grill (16)
  • Internet (15)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List
Nearby cities
Filter search results by:
Book Online(15)

Suitability

  • Wheelchair access (2)
  • Elder access (7)
  • Suitable for children (0)
  • Pet friendly (8)
  • Smoking allowed (0)

Amenities

  • Other outdoor space (19)
  • Washer/Dryer (19)
  • Parking (18)
  • Grill (16)
  • Internet (15)
  • View all amenities