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Holiday rentals in Great Barrington

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Top-rated holiday rentals in Great Barrington

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

ROOMS ON THE RIVER/Great Fly Fishing/Berkshires
Entire guest suite · 3 guests · 2 beds · 1 bathroom

ROOMS ON THE RIVER/Great Fly Fishing/BerkshiresCirca 1830 house located right on the Housatonic River was once the home of the local farrier. Two bedrooms, new bath, and a galley kitchenette with a single induction cooktop, full-sized refrigerator, oven, and microwave. There is a coffee station, and other varied electrical appliances too. Close to all Berkshire attractions (see Berkshires.org) and on a noted fly fishing section of the river, near skiing, hiking, kayaking, and shopping. Three miles to the local grocery store & shopping.

The Sunset Suite~Great South County Location!
Entire guest suite · 2 guests · 1 bed · 1 bathroom

The Sunset Suite~Great South County Location!Welcome to the Sunset Suite, a recently completed private air-conditioned upstairs space, that’s comfortable fresh and serene. This perfect couple’s retreat is located only a 10 minute drive from both Great Barrington and Sheffield, and sits on a hill surrounded by woods and farmland with spectacular views of our Berkshire Hills, and great sunsets!

Fun Main Street Apartment
Entire flat · 3 guests · 2 beds · 1 bathroom

Fun Main Street ApartmentCozy one bedroom apartment is perfect for a single person, couple or even three people (there is a futon couch in living room. Right on Main Street just a short walk away from shops and restaurants. Park your car in our off street parkin

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Popular amenities for Great Barrington holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Great Barrington

  1. Entire cottage
  2. Great Barrington
Artist Cottage at the Foot of Monument Mountain
₹15,146 per night
SUPERHOST
  1. Entire loft
  2. Sandisfield
Carriage House Loft - Tyringham
₹15,146 per night
  1. Entire flat
  2. Great Barrington
Another fun Main St location
₹8,043 per night
SUPERHOST
  1. Entire house
  2. Monterey
Sweet Monterey Cottage
₹13,977 per night
SUPERHOST
  1. Entire loft
  2. Great Barrington
The Old Red Barn
₹10,007 per night
SUPERHOST
  1. Tiny house
  2. Lee
Enchanted Tiny Tower at Santarella Gardens
₹18,646 per night
SUPERHOST
  1. Entire flat
  2. Stockbridge
Historic,Famous,Iconic, Unforgettable Berks Escape
₹15,146 per night
SUPERHOST
  1. Entire house
  2. Lee
Cozy Berkshires Cottage
₹8,628 per night
SUPERHOST
  1. Entire flat
  2. Great Barrington
Private En Suite in Beautiful Victorian
₹7,834 per night
SUPERHOST
  1. Entire cabin
  2. Monterey
Amazing Berkshire Mountains Cabin
₹24,736 per night
  1. Entire house
  2. Great Barrington
Cozy Great Barrington Cottage with Mountain View
₹24,130 per night
SUPERHOST
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  1. Entire house
  2. Egremont
Lakeside Cottage - A Waterfront Retreat in Great Location!
₹36,561 per night

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