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Jamaica, VT Holiday Rentals
Holiday Rentals
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Vermont (VT)
Jamaica, VT Holiday Rentals
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Internet or Wifi (76)
Washer/Dryer (69)
Other outdoor space (63)
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Kid friendly (70)
Pet friendly (27)
Smoking allowed (2)
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Holiday Rental House (67)
Condominium/Apartment (9)
Cabin Holiday Rental (0)
Private Room (0)
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Waterfront (9)
Boat Available (5)
Mountain Views (1)
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Distance from
5 km
Jamaica State Park
Bee Well Homestead
Elaine Beckwith Gallery
Hot Glass Works
Margie's Muse Handweaving & Gallery
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76 rentals
in Jamaica.
Mountain Oasis - Endless Outdoor Fun!
Holiday Rental House
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5 bedrooms
4 bathrooms
Sleeps 14
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Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton
56 reviews
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
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Two Bedroom Chalet, Charming, Quiet, River Front
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Authentic and comfortable Vermont log cabin - secluded yet near attractions
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
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Wishing Well Cabin
10 reviews
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
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One of a Kind Post and Beam Home on Private 100 acre Island
15 reviews
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 12
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*Shred Shack* Hot Tub w/ Majestic Valley Views
1 review
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 12
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Private Apt - 5 min drive to Stratton Mnt & 3 min WALK to Pikes Falls!!!
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 5
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Tiny House with fire place. 5 min from Stratton Mt. 3 min WALK from Pikes Falls!
Condo/Apartment
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0 bedrooms
1 bathroom
Sleeps 2
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Foxglove Tiny House - a modern tiny getaway
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Stratton Mountain On A Budget
4 reviews
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 3
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Stratton Mountain Ski House
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 7
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West Wing at Mantana Meadows on the West River
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 8
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Private Mountain Cottage With Hot Tub! Less than 2 Miles from Stratton Skiing!
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Warm & Inviting Jamaica Cabin w/ Grill: Ski & Hike
8 reviews
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
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This cabin is a 2 bedroom(s), 1.5 bathrooms, located in Jamaica, VT.
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
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Starry Skies: 7min to SkiStratton+PikesFalls+DogOK
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
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Rustic Cabin on Private Pond in Stratton Vermont
15 reviews
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
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Newly Designed Chalet w/Views, Minutes to Stratton
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
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Convenient 4-Bedroom Family Base: Work from Home, Fast WiFi, 15 min to ski!
Condo/Apartment
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4 bedrooms
1 bathroom
Sleeps 10
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The Pine Mountain Hideaway minutes to Stratton! 4BR / 2 Bth
3 reviews
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 16
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Celestial Mountain Hideaway
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
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Stratton Mountain location for less
8 reviews
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 10
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Secluded, cozy and affordable! Beautiful setting in the woods
32 reviews
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Minutes from Stratton Mountain for Less Money
59 reviews
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Cozy ski home with amazing views of Stratton & Bromley Mountains.
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 11
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New Beautiful Modern Home - Weekly or Monthly - Isolated but Centrally Located
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 10
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Stratton Mountain home in downtown Winhall
1 review
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 8
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A/C & Pool! Near Stratton & Bromley!
Condo/Apartment
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3 bedrooms
2 bathrooms
Sleeps 10
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Green Mountain Modern House: iconic modern getaway
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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The Overlook House: New Listing by Stratton Mountain
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 12
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Best of Vermont
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 12
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Sauna Nestled in the VT Mountains
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 7
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All Season Paradise. Swim, Hike, Ski and More!
8 reviews
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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True Vermont Experience! Spectacular home great for ski loving families!
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 10
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Contemporary gem with fireplace, large deck, grill, private hot tub & mtn views
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 10
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Perfect Family Retreat! Minutes From Stratton Mtn. Close To Mt. Snow & Bromley
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 10
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A great summer or winter house (condo) just a mile from Stratton mountain.
17 reviews
Condo/Apartment
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3 bedrooms
3 bathrooms
Sleeps 6
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Privacy in the Green Mountains! Hike, bike, swim and enjoy VT all summer.
25 reviews
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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This house is a 4 bedroom(s), 2.5 bathrooms, located in Jamaica, VT.
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 10
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Luxurious, 1&1/2 Miles to Stratton Mtn.
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 10
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3900 sqft, 4bd, 3ba - 5 min to Stratton w/Views!
15 reviews
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 13
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A PERFECT POST-N-BEAM IN THE CLOUDS OVER STRATTON
Holiday Rental House
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5 bedrooms
3 bathrooms
Sleeps 10
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Live & Breathe VT- Village Home, Yoga Studio, Ski!
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 9
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Historic, river view home with wood fireplaces, fast WiFi, & a washer/dryer
Holiday Rental House
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5 bedrooms
3 bathrooms
Sleeps 13
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Bluebird - Large cottage for all season getaway
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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Coffee Lover's Retreat w/ hot tub & game room
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 12
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Enjoy Privacy and Beautiful views of Southern VT
7 reviews
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 10
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STRATTON SKI HOUSE BUILT FOR FUN, HOT TUB, SAUNA, MAN CAVE, MORE
22 reviews
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 10
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Modern 5BR VT home minutes to Stratton w/ Sauna
Holiday Rental House
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5 bedrooms
3 bathrooms
Sleeps 12
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Showing results 1-50 of 76
Frequently Asked Questions about Jamaica
Do any holiday rentals in Jamaica have a pool?
Yes, here are some popular holiday rentals in Jamaica that have a pool:
A great summer or winter house (condo) just a mile from Stratton mountain.
Mountain Oasis - Endless Outdoor Fun!
Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton
See all holiday rentals with a pool in Jamaica on Tripadvisor
Do any holiday rentals in Jamaica have internet access?
Yes, here are some popular holiday rentals in Jamaica that have internet access:
Mountain Oasis - Endless Outdoor Fun!
Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton
Two Bedroom Chalet, Charming, Quiet, River Front
See all holiday rentals in Jamaica on Tripadvisor
What are the best pet friendly rentals in Jamaica?
The best pet friendly rentals in Jamaica are:
Mountain Oasis - Endless Outdoor Fun!
*Shred Shack* Hot Tub w/ Majestic Valley Views
Private Apt - 5 min drive to Stratton Mnt & 3 min WALK to Pikes Falls!!!
See all pet friendly holiday rentals in Jamaica on Tripadvisor
What are some great rentals in Jamaica that are kid friendly?
Some of the most popular kid friendly rentals in Jamaica are:
Mountain Oasis - Endless Outdoor Fun!
Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton
Two Bedroom Chalet, Charming, Quiet, River Front
See all kid friendly holiday rentals in Jamaica on Tripadvisor