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Jamaica Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
70 rentals in Jamaica.
Private Apt - 5 min drive to Stratton Mnt & 3 min WALK to Pikes Falls!!!, vacation rental in Jamaica
Private Apt - 5 min drive to Stratton Mnt & 3 min WALK to Pikes Falls!!!, vacation rental in Jamaica
Private Apt - 5 min drive to Stratton Mnt & 3 min WALK to Pikes Falls!!!, vacation rental in Jamaica

Private Apt - 5 min drive to Stratton Mnt & 3 min WALK to Pikes Falls!!!

Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Spacious Riverfront Home 7 Minutes to Stratton!, vacation rental in Jamaica
Spacious Riverfront Home 7 Minutes to Stratton!, vacation rental in Jamaica
Spacious Riverfront Home 7 Minutes to Stratton!, vacation rental in Jamaica

Spacious Riverfront Home 7 Minutes to Stratton!

Rental Home
5 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Sauna Nestled in the VT Mountains, vacation rental in Jamaica
Sauna Nestled in the VT Mountains, vacation rental in Jamaica
Sauna Nestled in the VT Mountains, vacation rental in Jamaica

Sauna Nestled in the VT Mountains

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Authentic and comfortable Vermont log cabin - secluded yet near attractions, vacation rental in Jamaica
Authentic and comfortable Vermont log cabin - secluded yet near attractions, vacation rental in Jamaica
Authentic and comfortable Vermont log cabin - secluded yet near attractions, vacation rental in Jamaica

Authentic and comfortable Vermont log cabin - secluded yet near attractions

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton, vacation rental in Jamaica
Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton, vacation rental in Jamaica
Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton, vacation rental in Jamaica

Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Plenty of Room For Everyone! - 5 Minutes to Stratton, vacation rental in Jamaica
Plenty of Room For Everyone! - 5 Minutes to Stratton, vacation rental in Jamaica
Plenty of Room For Everyone! - 5 Minutes to Stratton, vacation rental in Jamaica

Plenty of Room For Everyone! - 5 Minutes to Stratton

Rental Home
4 bedrooms
4 bathrooms
Sleeps 17
Match: Sleeps
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Potter's Place | House in Jamaica with mountain views, vacation rental in Jamaica
Potter's Place | House in Jamaica with mountain views, vacation rental in Jamaica
Potter's Place | House in Jamaica with mountain views, vacation rental in Jamaica

Potter's Place | House in Jamaica with mountain views

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cool Runnings Cabin: Open-Concept near Stratton, vacation rental in Jamaica
Cool Runnings Cabin: Open-Concept near Stratton, vacation rental in Jamaica
Cool Runnings Cabin: Open-Concept near Stratton, vacation rental in Jamaica

Cool Runnings Cabin: Open-Concept near Stratton

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Tiny House with fire place. 5 min from Stratton Mt. 3 min WALK from Pikes Falls!, vacation rental in Jamaica
Tiny House with fire place. 5 min from Stratton Mt. 3 min WALK from Pikes Falls!, vacation rental in Jamaica
Tiny House with fire place. 5 min from Stratton Mt. 3 min WALK from Pikes Falls!, vacation rental in Jamaica

Tiny House with fire place. 5 min from Stratton Mt. 3 min WALK from Pikes Falls!

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Green Mountain Tiny House: a mountainside retreat, vacation rental in Jamaica
Green Mountain Tiny House: a mountainside retreat, vacation rental in Jamaica
Green Mountain Tiny House: a mountainside retreat, vacation rental in Jamaica

Green Mountain Tiny House: a mountainside retreat

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Two Bedroom Chalet, Charming, Quiet, River Front, vacation rental in Jamaica
Two Bedroom Chalet, Charming, Quiet, River Front, vacation rental in Jamaica
Two Bedroom Chalet, Charming, Quiet, River Front, vacation rental in Jamaica

Two Bedroom Chalet, Charming, Quiet, River Front

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Foxglove Tiny House - a modern tiny getaway, vacation rental in Jamaica
Foxglove Tiny House - a modern tiny getaway, vacation rental in Jamaica
Foxglove Tiny House - a modern tiny getaway, vacation rental in Jamaica

Foxglove Tiny House - a modern tiny getaway

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Stratton Mountain On A Budget, vacation rental in Jamaica
Stratton Mountain On A Budget, vacation rental in Jamaica
Stratton Mountain On A Budget, vacation rental in Jamaica

Stratton Mountain On A Budget

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Stratton Mountain Ski House, vacation rental in Jamaica
Stratton Mountain Ski House, vacation rental in Jamaica
Stratton Mountain Ski House, vacation rental in Jamaica

Stratton Mountain Ski House

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Warm & Inviting Jamaica Cabin w/ Grill: Ski & Hike, vacation rental in Jamaica
Warm & Inviting Jamaica Cabin w/ Grill: Ski & Hike, vacation rental in Jamaica
Warm & Inviting Jamaica Cabin w/ Grill: Ski & Hike, vacation rental in Jamaica

Warm & Inviting Jamaica Cabin w/ Grill: Ski & Hike

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private Mountain Cottage With Hot Tub!  Less than 2 Miles from Stratton Skiing!, vacation rental in Jamaica
Private Mountain Cottage With Hot Tub!  Less than 2 Miles from Stratton Skiing!, vacation rental in Jamaica
Private Mountain Cottage With Hot Tub!  Less than 2 Miles from Stratton Skiing!, vacation rental in Jamaica

Private Mountain Cottage With Hot Tub! Less than 2 Miles from Stratton Skiing!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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West Wing at Mantana Meadows on the West River, vacation rental in Jamaica
West Wing at Mantana Meadows on the West River, vacation rental in Jamaica
West Wing at Mantana Meadows on the West River, vacation rental in Jamaica

West Wing at Mantana Meadows on the West River

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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This house is a 2 bedroom(s), 1 bathrooms, located in Jamaica, VT., vacation rental in Jamaica
This house is a 2 bedroom(s), 1 bathrooms, located in Jamaica, VT., vacation rental in Jamaica
This house is a 2 bedroom(s), 1 bathrooms, located in Jamaica, VT., vacation rental in Jamaica

This house is a 2 bedroom(s), 1 bathrooms, located in Jamaica, VT.

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Starry Skies: 7min to SkiStratton+PikesFalls+DogOK, vacation rental in Jamaica
Starry Skies: 7min to SkiStratton+PikesFalls+DogOK, vacation rental in Jamaica
Starry Skies: 7min to SkiStratton+PikesFalls+DogOK, vacation rental in Jamaica

Starry Skies: 7min to SkiStratton+PikesFalls+DogOK

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Rustic Cabin on Private Pond in Stratton Vermont, vacation rental in Jamaica
Rustic Cabin on Private Pond in Stratton Vermont, vacation rental in Jamaica
Rustic Cabin on Private Pond in Stratton Vermont, vacation rental in Jamaica

Rustic Cabin on Private Pond in Stratton Vermont

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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This cabin is a 2 bedroom(s), 1.5 bathrooms, located in Jamaica, VT., vacation rental in Jamaica
This cabin is a 2 bedroom(s), 1.5 bathrooms, located in Jamaica, VT., vacation rental in Jamaica
This cabin is a 2 bedroom(s), 1.5 bathrooms, located in Jamaica, VT., vacation rental in Jamaica

This cabin is a 2 bedroom(s), 1.5 bathrooms, located in Jamaica, VT.

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Celestial Mountain Hideaway, vacation rental in Jamaica
Celestial Mountain Hideaway, vacation rental in Jamaica
Celestial Mountain Hideaway, vacation rental in Jamaica

Celestial Mountain Hideaway

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Convenient 4-Bedroom Family Base: Work from Home, Fast WiFi, 15 min to ski!, vacation rental in Jamaica
Convenient 4-Bedroom Family Base: Work from Home, Fast WiFi, 15 min to ski!, vacation rental in Jamaica
Convenient 4-Bedroom Family Base: Work from Home, Fast WiFi, 15 min to ski!, vacation rental in Jamaica

Convenient 4-Bedroom Family Base: Work from Home, Fast WiFi, 15 min to ski!

Condo/Apartment
4 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Stratton Mountain location for less, vacation rental in Jamaica
Stratton Mountain location for less, vacation rental in Jamaica
Stratton Mountain location for less, vacation rental in Jamaica

Stratton Mountain location for less

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Secluded, cozy and affordable!  Beautiful setting in the woods, vacation rental in Jamaica
Secluded, cozy and affordable!  Beautiful setting in the woods, vacation rental in Jamaica
Secluded, cozy and affordable!  Beautiful setting in the woods, vacation rental in Jamaica

Secluded, cozy and affordable! Beautiful setting in the woods

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Wishing Well Cabin, vacation rental in Jamaica
Wishing Well Cabin, vacation rental in Jamaica
Wishing Well Cabin, vacation rental in Jamaica

Wishing Well Cabin

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Plush Vermont ski + summer chalet in serene Jamaica Vermont!, vacation rental in Jamaica
Plush Vermont ski + summer chalet in serene Jamaica Vermont!, vacation rental in Jamaica
Plush Vermont ski + summer chalet in serene Jamaica Vermont!, vacation rental in Jamaica

Plush Vermont ski + summer chalet in serene Jamaica Vermont!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Minutes from Stratton Mountain for Less Money, vacation rental in Jamaica
Minutes from Stratton Mountain for Less Money, vacation rental in Jamaica
Minutes from Stratton Mountain for Less Money, vacation rental in Jamaica

Minutes from Stratton Mountain for Less Money

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy ski retreat 7 minutes from Stratton's Sunbowl!, vacation rental in Jamaica
Cozy ski retreat 7 minutes from Stratton's Sunbowl!, vacation rental in Jamaica
Cozy ski retreat 7 minutes from Stratton's Sunbowl!, vacation rental in Jamaica

Cozy ski retreat 7 minutes from Stratton's Sunbowl!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Newly Designed Chalet w/Views, Minutes to Stratton, vacation rental in Jamaica
Newly Designed Chalet w/Views, Minutes to Stratton, vacation rental in Jamaica
Newly Designed Chalet w/Views, Minutes to Stratton, vacation rental in Jamaica

Newly Designed Chalet w/Views, Minutes to Stratton

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy ski home with amazing views of Stratton & Bromley Mountains., vacation rental in Jamaica
Cozy ski home with amazing views of Stratton & Bromley Mountains., vacation rental in Jamaica
Cozy ski home with amazing views of Stratton & Bromley Mountains., vacation rental in Jamaica

Cozy ski home with amazing views of Stratton & Bromley Mountains.

Rental Home
4 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Stratton Mountain home in downtown Winhall, vacation rental in Jamaica
Stratton Mountain home in downtown Winhall, vacation rental in Jamaica
Stratton Mountain home in downtown Winhall, vacation rental in Jamaica

Stratton Mountain home in downtown Winhall

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Green Mountain Modern House: iconic modern getaway, vacation rental in Jamaica
Green Mountain Modern House: iconic modern getaway, vacation rental in Jamaica
Green Mountain Modern House: iconic modern getaway, vacation rental in Jamaica

Green Mountain Modern House: iconic modern getaway

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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A/C & Pool! Near Stratton & Bromley!, vacation rental in Jamaica
A/C & Pool! Near Stratton & Bromley!, vacation rental in Jamaica
A/C & Pool! Near Stratton & Bromley!, vacation rental in Jamaica

A/C & Pool! Near Stratton & Bromley!

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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The Overlook House: New Listing by Stratton Mountain, vacation rental in Jamaica
The Overlook House: New Listing by Stratton Mountain, vacation rental in Jamaica
The Overlook House: New Listing by Stratton Mountain, vacation rental in Jamaica

The Overlook House: New Listing by Stratton Mountain

Rental Home
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Best of Vermont, vacation rental in Jamaica
Best of Vermont, vacation rental in Jamaica
Best of Vermont, vacation rental in Jamaica

Best of Vermont

Rental Home
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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All Season Paradise. Swim, Hike, Ski and More!, vacation rental in Jamaica
All Season Paradise. Swim, Hike, Ski and More!, vacation rental in Jamaica
All Season Paradise. Swim, Hike, Ski and More!, vacation rental in Jamaica

All Season Paradise. Swim, Hike, Ski and More!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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True Vermont Experience! Spectacular home great for ski loving families!, vacation rental in Jamaica
True Vermont Experience! Spectacular home great for ski loving families!, vacation rental in Jamaica
True Vermont Experience! Spectacular home great for ski loving families!, vacation rental in Jamaica

True Vermont Experience! Spectacular home great for ski loving families!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Contemporary gem with fireplace, large deck, grill, private hot tub & mtn views, vacation rental in Jamaica
Contemporary gem with fireplace, large deck, grill, private hot tub & mtn views, vacation rental in Jamaica
Contemporary gem with fireplace, large deck, grill, private hot tub & mtn views, vacation rental in Jamaica

Contemporary gem with fireplace, large deck, grill, private hot tub & mtn views

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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A great summer or winter house (condo) just a mile from Stratton mountain., vacation rental in Jamaica
A great summer or winter house (condo) just a mile from Stratton mountain., vacation rental in Jamaica
A great summer or winter house (condo) just a mile from Stratton mountain., vacation rental in Jamaica

A great summer or winter house (condo) just a mile from Stratton mountain.

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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A Secluded Haven for Your Family Vacation!, vacation rental in Jamaica
A Secluded Haven for Your Family Vacation!, vacation rental in Jamaica
A Secluded Haven for Your Family Vacation!, vacation rental in Jamaica

A Secluded Haven for Your Family Vacation!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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This house is a 4 bedroom(s), 2.5 bathrooms, located in Jamaica, VT., vacation rental in Jamaica
This house is a 4 bedroom(s), 2.5 bathrooms, located in Jamaica, VT., vacation rental in Jamaica
This house is a 4 bedroom(s), 2.5 bathrooms, located in Jamaica, VT., vacation rental in Jamaica

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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Perfect Family Retreat! Minutes From Stratton Mtn. Close To Mt. Snow & Bromley, vacation rental in Jamaica
Perfect Family Retreat! Minutes From Stratton Mtn. Close To Mt. Snow & Bromley, vacation rental in Jamaica
Perfect Family Retreat! Minutes From Stratton Mtn. Close To Mt. Snow & Bromley, vacation rental in Jamaica

Perfect Family Retreat! Minutes From Stratton Mtn. Close To Mt. Snow & Bromley

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Privacy in the Green Mountains! Hike, bike, swim and enjoy VT all summer., vacation rental in Jamaica
Privacy in the Green Mountains! Hike, bike, swim and enjoy VT all summer., vacation rental in Jamaica
Privacy in the Green Mountains! Hike, bike, swim and enjoy VT all summer., vacation rental in Jamaica

Privacy in the Green Mountains! Hike, bike, swim and enjoy VT all summer.

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Luxurious, 1&1/2 Miles to Stratton Mtn., vacation rental in Jamaica
Luxurious, 1&1/2 Miles to Stratton Mtn., vacation rental in Jamaica
Luxurious, 1&1/2 Miles to Stratton Mtn., vacation rental in Jamaica

Luxurious, 1&1/2 Miles to Stratton Mtn.

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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*Shred Shack* Hot Tub w/ Majestic Valley Views, vacation rental in Jamaica
*Shred Shack* Hot Tub w/ Majestic Valley Views, vacation rental in Jamaica
*Shred Shack* Hot Tub w/ Majestic Valley Views, vacation rental in Jamaica

*Shred Shack* Hot Tub w/ Majestic Valley Views

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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3900 sqft,  4bd, 3ba - 5 min to Stratton w/Views!, vacation rental in Jamaica
3900 sqft,  4bd, 3ba - 5 min to Stratton w/Views!, vacation rental in Jamaica
3900 sqft,  4bd, 3ba - 5 min to Stratton w/Views!, vacation rental in Jamaica

3900 sqft, 4bd, 3ba - 5 min to Stratton w/Views!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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A PERFECT POST-N-BEAM IN THE CLOUDS OVER STRATTON, vacation rental in Jamaica
A PERFECT POST-N-BEAM IN THE CLOUDS OVER STRATTON, vacation rental in Jamaica
A PERFECT POST-N-BEAM IN THE CLOUDS OVER STRATTON, vacation rental in Jamaica

A PERFECT POST-N-BEAM IN THE CLOUDS OVER STRATTON

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Stratton Mountain Escape w Hot Tub Deck Projector, vacation rental in Jamaica
Stratton Mountain Escape w Hot Tub Deck Projector, vacation rental in Jamaica
Stratton Mountain Escape w Hot Tub Deck Projector, vacation rental in Jamaica

Stratton Mountain Escape w Hot Tub Deck Projector

Rental Home
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Jamaica Vacation Home w/ Deck: 8 Mi to Skiing!, vacation rental in Jamaica
Jamaica Vacation Home w/ Deck: 8 Mi to Skiing!, vacation rental in Jamaica
Jamaica Vacation Home w/ Deck: 8 Mi to Skiing!, vacation rental in Jamaica

Jamaica Vacation Home w/ Deck: 8 Mi to Skiing!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Showing results 1-50 of 70
Frequently Asked Questions about Jamaica