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Great Barrington Vacation Rentals

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    1 / 12
    5 of 5 bubbles (21) Excellent
    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    5 of 5 bubbles (3) Excellent
    Great Barrington
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Great Barrington
    4 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    1 / 18
    Great Barrington
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Balcony
    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • ?
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    • x
    About this property
    Restored 1940's log cabin, amazing undisturbed 30 mile, 180 degree views. Hilltop location, walking distance to the village of South Egremont, ideal for hiking, Appalachian trail nearby, minutes to all major Berkshire attractions, very private & quiet, abundant wildlife, deer, fox, hawks, turkey.... View all property information
    Location Information
    Great Barrington, Berkshires
    1 / 14
    5 of 5 bubbles (1) Excellent
    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
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    • Mountain Views
    • Washer
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    • x
    • ?
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    • x
    About this property
    Elegant, contemporary one bedroom house sleeps 4. Great central location. Peace, beauty and convenience. Perfectly located for all Berkshires activities, while still maintaining privacy and quiet. All new construction. This is my mother-in-law's property (I handle her online reservations) and... View all property information
    Location Information
    Great Barrington, Berkshires 01230
    1 / 27
    3.5 of 5 bubbles (2) Average
    Great Barrington
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Porch
    • Grill
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    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Shaker Hill is a quirky rambling farmhouse located less than 3 hours from NYC and Boston. Hidden away down a 400’ unpaved driveway on 30 acres of fields and forest in the heart of the Berkshires, Shaker Hill is totally private and surrounded by 30 acres of rolling fields, diverse wetlands,... View all property information
    Location Information
    Great Barrington, Berkshires 01230
    3 of 5 bubbles Reviewed September 11, 2014
    This is a very large house, more than adequate in size for a group of ten people. It has a big yard and a spectacular view of the mountains, especially from an upstairs window...
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    1 / 14
    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Wi-Fi
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    • Mountain Views
    • Private Yard
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    • Pet-friendly
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    • ?
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    • x
    About this property
    One bedroom, one bathroom cottage on beautiful country road. Private garden and screened-in porch. Two miles to shops and restaurants of downtown Great Barrington. Enjoy nearby skiing, cycling, fishing, hiking and golf.<BR><BR>The Space:<BR><BR>Quaint cottage with wood burning stove. Ideal base for... View all property information
    Location Information
    Great Barrington, Berkshires 01230
    1 / 10
    4 of 5 bubbles (1) Very good
    Great Barrington
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Outdoor Dining Area
    • DVD Player
    • Parking
    • Porch
    • Internet Access
    • Washer
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Our home is located in Great Barrington, given the title of the #1 Best Small Town in America by Smithsonian Magazine. There are many great restaurants, shopping, the Mahaiwe theater, a cineplex, golf, natural foods Co-op, a State Forest, yoga studio, and more. There are about twelve (12!) hiking... View all property information
    Location Information
    Great Barrington, Berkshires 01230
    1 / 12
    1 of 5 bubbles (1) Terrible
    Great Barrington
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Washer
    • Satellite TV
    • Internet Access
    • Mountain Views
    • Grill
    • DVD Player
    • Waterfront
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    Located in a wooded area overlooking a pristine lake, this woodsy style contemporary is a sportsman's paradise. It's a short drive to skiing (Jiminy Peak, Butternut, Catamount) and cultural attractions, (Tanglewood, National Music Center, Aston Magna, etc.) or you can fish, swim, boat, hike, or... View all property information
    Location Information
    Great Barrington, Berkshires 01236
    1 / 25
    Great Barrington
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Internet Access
    • Mountain Views
    • Satellite TV
    • Patio
    • DVD Player
    • Private Outdoor...
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This home is uniquely and magnificently furnished by a retired couple that spent 18 years traveling and living abroad. Even local real estate agents have called the house “special”. It has 6,700 sf of living space (3 floors) with plenty of places to be together or to be alone (as one so chooses).... View all property information
    Location Information
    Great Barrington, Berkshires 01230
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    1 / 6
    Great Barrington
    9 Bedrooms, 8 Bathrooms, Sleeps 16 | Quick View
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    • Grill
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    • Washer
    • Hot Tub
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    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This is by far one of the nicest homes that you will come across in the area (or this site for that matter!). The estate comes complete with 7 bedroom, 7 bathroom main house, a guest house with 2 bedrooms and one bath, several fire places, a pool table, ping pong table, pool, jacuzzi, several TV's... View all property information
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    Great Barrington, Berkshires 01230
    1 / 14
    Great Barrington
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Patio
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    • ?
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    • x
    Location Information
    Great Barrington, Berkshires 01230
    1 / 16
    Great Barrington
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
    • DVD Player
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    • Central Heating
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    • Pet-friendly
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    • ?
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    • x
    Location Information
    Great Barrington, Berkshires 01230
    1 / 24
    Great Barrington
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Internet Access
    • Satellite TV
    • Hot Tub
    • DVD Player
    • Patio
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    Location Information
    Great Barrington, Berkshires 01230
    1 / 23
    Great Barrington
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Housekeeping...
    • Patio
    • Balcony
    • Internet Access
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    • Grill
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    Location Information
    Great Barrington, Berkshires 01230
    1 / 23
    Great Barrington
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    Location Information
    Great Barrington, Berkshires 01230
    1 / 23
    Great Barrington
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Private Outdoor...
    • Housekeeping...
    • DVD Player
    • Air Conditioning
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
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    Great Barrington, Berkshires 01230
    1 / 23
    Great Barrington
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • ?
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    • x
    Location Information
    Great Barrington, Berkshires 01230
    1 / 15
    Great Barrington
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Grill
    • Patio
    • Internet Access
    • Parking
    • DVD Player
    • Washer
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    • Pet-friendly
    • Child-friendly
    • ?
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    • x
    Location Information
    Great Barrington, Berkshires 01230
    1 / 22
    Great Barrington
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
    • Satellite TV
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    • DVD Player
    • Grill
    • Parking
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    Location Information
    Great Barrington, Berkshires 01230
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    1 / 16
    Great Barrington
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Washer
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    • Pet-friendly
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    • x
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    Location Information
    Great Barrington, Berkshires 01230
    1 / 23
    Great Barrington
    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Internet Access
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    • Shared Outdoor Pool...
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    • Pet-friendly
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    • ?
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    • x
    Location Information
    Great Barrington, Berkshires 01230
    1 / 14
    Great Barrington
    6 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
    • DVD Player
    • Internet Access
    • Washer
    • Balcony
    • Central Heating
    • Patio
    • Grill
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    • Pet-friendly
    • Child-friendly
    • ?
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    • x
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    Great Barrington, Berkshires 01230
    1 / 23
    Great Barrington
    2 Bedrooms, 1 Bathroom, Sleeps 10 | Quick View
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    • DVD Player
    • Internet Access
    • Grill
    • Washer
    • Balcony
    • Satellite TV
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    • Pet-friendly
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    • ?
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    Great Barrington, Berkshires 01230
    1 / 21
    Great Barrington
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • ?
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    • x
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    Great Barrington, Berkshires 01230
    1 / 23
    Great Barrington
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • ?
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    • x
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    Great Barrington, Berkshires 01230
    1 / 23
    Great Barrington
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Parking
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    • Patio
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
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    Great Barrington, Berkshires 01230
    1 / 24
    Great Barrington
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Air Conditioning
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    • Pet-friendly
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    • x
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    • x
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    Great Barrington, Berkshires 01230
    1 / 24
    Great Barrington
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Air Conditioning
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    • x
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    Great Barrington, Berkshires 01230
    1 / 23
    Great Barrington
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Pet-friendly
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    • x
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    • x
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    Great Barrington, Berkshires 01230
    1 / 24
    Great Barrington
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Washer
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    • ?
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    Great Barrington, Berkshires 01230
    1 / 17
    Great Barrington
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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    • Pet-friendly
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    • x
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    Great Barrington, Berkshires 01230
    1 / 22
    Great Barrington
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • ?
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    Great Barrington, Berkshires 01230
    1 / 16
    Great Barrington
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • Grill
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    • x
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    Great Barrington, Berkshires 01230
    1 / 23
    Great Barrington
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    Great Barrington, Berkshires 01230
    1 / 23
    Great Barrington
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Great Barrington, Berkshires 01230
    1 / 21
    Great Barrington
    Studio, 1 Bathroom, Sleeps 3 | Quick View
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    • x
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    Great Barrington, Berkshires 01230
    1 / 13
    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Great Barrington, Berkshires 01230
    1 / 13
    Great Barrington
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Great Barrington, Berkshires 01230
    1 / 19
    Great Barrington
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Great Barrington, Berkshires 01230
    1 / 24
    Great Barrington
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Great Barrington, Berkshires 01230
    1 / 24
    Great Barrington
    10 Bedrooms, 4 Bathrooms, Sleeps 20 | Quick View
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    Great Barrington, Berkshires 01230
    1 / 23
    Great Barrington
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    Great Barrington, Berkshires 01230
    1 / 24
    Great Barrington
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Great Barrington, Berkshires 01230
    1 / 24
    Great Barrington
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • x
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    Great Barrington, Berkshires 01230
    1 / 21
    Great Barrington
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Great Barrington, Berkshires 01230
    1 / 24
    Great Barrington
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    Great Barrington, Berkshires 01230
    1 / 24
    Great Barrington
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    Great Barrington, Berkshires 01230
    1 / 18
    Great Barrington
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Location Information
    Great Barrington, Berkshires 01230

    The following rentals are within 5 miles of Great Barrington, Massachusetts.

    1 / 52
    5 of 5 bubbles (10) Excellent
    North Egremont
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    About this property
    Located in the Berkshire mountains on more than 5 acres <BR>surrounded by 29 acres of conservation land. Featuring<BR>beautiful views of meadows, mountains and farm land bordering the crystal clear Green River (great trout fishing).Only 10 minutes from Great Barrington's Main Street stores,... View all property information
    Location Information
    North Egremont, Berkshires 01230
    5 of 5 bubbles Reviewed March 14, 2017
    I was very skeptical about staying somewhere other than a "chain hotel or resort". That is until I met Barbara and Phil. They were a very gracious, humble and warm couple who made...
    5 of 5 bubbles Reviewed November 16, 2016
    River Song is a wonderfully private and relaxing place to hang your hat before heading out to visit Great Barrington and all the beauty that the Berkshires offers in any season...
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    Great Barrington Flight and Weather Info
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    BDL
    Bradley Intl Airport
    39.0 miles from Great Barrington
    Low airfares recently found by TripAdvisor travelers
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