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Vacation rentals in Jamaica

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Top-rated vacation rentals in Jamaica

Guests agree: these stays are highly rated for location, cleanliness, and more.

Romantic Wooded Vermont Cabin
SUPERHOST
Entire cabin · 2 guests · 1 bed · 1 bath
Romantic Wooded Vermont CabinEnjoy this private getaway for two in our charming and rustic home nestled on a peaceful, wooded lot at the edge of a national forest. First floor only, open floor plan and it's all yours! Conveniently located 2 miles from Jamaica Village, 10 miles from Stratton Mountain, 16 miles from Manchester and 30 miles north of Brattleboro.
Private 2BR Getaway to Southern VT Adventures
Entire rental unit · 4 guests · 2 beds · 1 bath
Private 2BR Getaway to Southern VT AdventuresTake advantage of all that Southern Vermont offers while staying in our uniquely renovated 1850’s carriage barn. Jamaica Village is 15 minutes to Stratton Mountain, 20 minutes to Magic, Snow, and Bromley, hiking trails, and cross country skiing, and 40 minutes to Okemo. Walk to Jamaica State Park or visit shops, galleries, farmers markets, and restaurants minutes away. After your adventures, relax in your comfortable home away from home.
Rustic A-Frame Getaway Cabin (8min from Stratton!)
SUPERHOST
Entire cabin · 10 guests · 7 beds · 2 baths
Rustic A-Frame Getaway Cabin (8min from Stratton!)COVID-19: click 'read more' and scroll down for update. Charming rustic expanded A-frame cabin in the beautiful woods of Vermont. An excellent getaway in all seasons: 8 min drive to Stratton Mountain for skiing in the winter, 15 min drive to see maple sugaring in the spring, 10 min walk to Pikes Falls waterfall/swimming hole in the summer, and no drive needed to see stunning foliage in the fall. The perfect place to unplug and relax with a fire in the wood stove and a board game on the table!

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Other great vacation rentals in Jamaica

  1. Entire cabin
  2. Windham
The Shaker Chalet - Cabin Central to 5 Ski Areas
$275 per night
  1. Entire residential home
  2. Jamaica
Peaceful home set on 50 acres of fields and forest
$148 per night
  1. Entire chalet
  2. Winhall
Spacious Chalet W/ Endless Entertainment THE BARN
$957 per night
SUPERHOST
  1. Entire rental unit
  2. Londonderry
Cozy Suite in a Historic Building Near Ski Resorts
$128 per night
SUPERHOST
  1. Entire residential home
  2. Wardsboro
Cozy Vermont getaway near Mount Snow & Stratton
$287 per night
  1. Entire cabin
  2. Wardsboro
*NEW* Stylish 3 bed cabin btwn Mt. Snow & Stratton
$450 per night
SUPERHOST
  1. Tiny house
  2. Jamaica
Bright Sunny Studio, Farm House Tiny Living
$113 per night
SUPERHOST
  1. Entire residential home
  2. Wardsboro
Mt. Snow/Stratton Mtn House - Hot Tub & Game Room
$555 per night
SUPERHOST
  1. Entire cottage
  2. Jamaica
Ski Cottage in Woods-Privacy-7 min to Stratton Mtn
$164 per night
SUPERHOST
  1. Barn
  2. Jamaica
The Rafters Lodge
$185 per night
SUPERHOST
  1. Entire rental unit
  2. Jamaica
The Getaway
$136 per night
SUPERHOST
  1. Entire condominium (condo)
  2. Stratton
Cozy condo within walking distance to the slopes.
$346 per night