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Holiday rentals in The Berkshires

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Top-rated holiday rentals in The Berkshires

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

Rustic charmer perfect for a wintry country escape
Entire cabin · 2 guests · 1 bed · 1 bathroom
Rustic charmer perfect for a wintry country escapeTake it easy at this unique and tranquil getaway.
Peaceful Getaway in the Berkshires
SUPERHOST
Entire cottage · 4 guests · 3 beds · 1 bathroom
Peaceful Getaway in the BerkshiresPrivate home located in Berkshires only minutes from the Appalachian trail, Otis Ridge, and the Otis Reservoir. The private retreat sits on over an acre of land and is within walking distance to the Farmington River. Lee's premium outlets, dispensary, shopping, restaurants, and bars are located only a short drive away.
Jaw dropping mountain & lake views
SUPERHOST
Entire residential home · 9 guests · 5 beds · 2 bathrooms
Jaw dropping mountain & lake viewsCurl up with a good book by the fire and gaze out at the dreamy picturesque mountain and lake views..... Or ski, swim, hike and enjoy so much more that the Berkshires has to offer in this centrally located Southern Berkshire county home. Private mountain top adventure awaits.. Centrally located in Southern Berkshire County: 10 minutes from Butternut ski, 20 minutes to Great Barrington, 25 minutes Stockbridge & Lenox and 2 ½ hours from NYC and Boston.

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Other great holiday rentals in The Berkshires

SUPERHOST
  1. Entire residential home
  2. Monterey
Lakefront Treehouse in the Berkshires
SUPERHOST
  1. Entire rental unit
  2. Monterey
Hupi House: a stylish, cozy Berkshires lake house in Monterey
SUPERHOST
  1. Entire cabin
  2. Sandisfield
Iconic Cabin in the Berkshires
  1. Entire cabin
  2. Sandisfield
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
SUPERHOST
  1. Entire rental unit
  2. Sandisfield
Sunny Berkshire Studio Apartment
SUPERHOST
  1. Entire chalet
  2. Otis
Octagonal Glass Treehouse in Berkshires
SUPERHOST
  1. Entire residential home
  2. Otis
The Meadows House @ Otis Ridge w/ 7-person hot tub
SUPERHOST
  1. Entire cabin
  2. Sandisfield
Berkshires Cabin in Woods with Mountain Views
SUPERHOST
  1. Entire cabin
  2. Otis
Cozy cabin in the Berkshires
SUPERHOST
  1. Entire residential home
  2. Monterey
Beautiful Berkshire family house!
SUPERHOST
  1. Entire residential home
  2. Otis
Don't Have Buyers Remorse, Book Now Before It's Too Late, Stunning Carriage House That Ticks All The Boxes
SUPERHOST
  1. Entire cabin
  2. Monterey
Exotic Mountain Retreat in the Berkshires