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Holiday Rentals in Great Barrington, MA

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    All 17 Rentals in Great Barrington
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    Travellers to Great Barrington are booking July dates now. Secure your holiday home today, and have the perfect trip.
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    ₹23,917
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    1 / 27
    3.5 of 5 stars (2) Average
    5 Bedrooms / 4 Bathrooms / Sleeps 10
    travellers have booked this property
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    ₹19,134
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    1 / 23
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    ₹12,054
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    1 / 10
    5 of 5 stars (12) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 3
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    ₹43,051
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    1 / 22
    4 Bedrooms / 6 Bathrooms / Sleeps 12
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This immaculate home is the place for relaxing, entertaining and sharing great times with family and friends. The house sets over 4 beautifully wooded acres. We call it the 'illision of seclusion,' as it is very private and yet is 5 minutes from the town as well as lakes, hiking, movies, theater,... View all property information
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    Great Barrington, Berkshires 01236
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    ₹12,756
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    1 / 11
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travellers have booked this property
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    • Air Conditioning
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Welcome to our School House Cottage located in the heart of the Berkshires. Set in front of the ledges of Warner Mountain, this historic home was originally a three room schoolhouse. An addition in the 1960's transformed it into a private home which it remained for many years. Now updated, the... View all property information
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    Great Barrington, Berkshires 01237
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    ₹22,323
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    1 / 11
    5 of 5 stars (1) Excellent
    4 Bedrooms / 2 Bathrooms / Sleeps 9
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    The perfect house for friends and family to share! Bright,uncluttered, and inviting, with privacy and views just minutes to town. There are two fireplaces,a sunken living room, dining room with seating for 10, 4 bedrooms, 2 full bathrooms, and a cozy hang out area in the basement. There is a washer... View all property information
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    Great Barrington, Berkshires 01230
    5 of 5 stars Reviewed 6 February 2015
    This was the first time we had a rental cottage, but it surpassed all of our expectations. The cottage was clean and well arranged. Kitchen was spacious enough for more than a few...
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    ₹287,008
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    1 / 25
    6 Bedrooms / 6 Bathrooms / Sleeps 12
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Gym
    • Internet Access
    • Mountain Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • 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 7,000 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
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    Location Information
    Great Barrington, Berkshires 01230
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    ₹156,260
    / Week
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    1 / 9
    5 Bedrooms / 3 Bathrooms / Sleeps 10
    traveller have booked this property
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    Amenities & Details
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Attractive year-round lakefront house in a wooded area on a pristine Round Pond in the Berkshires. Relax and enjoy the view from your deck or dock. Fish from the dock or take the boat out onto the lake. Ideal family retreat in Great Barrington and only a short drive to cultural attractions... View all property information
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    Great Barrington, Berkshires 01236
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    ₹15,945
    / Night
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    1 / 19
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Mountain Views
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Surrounded by one of the most beautiful gardens in the Berkshires, Maya's Garden House is an outstanding example of an 18th century barn converted into a modern, comfortable, semi-secluded home. Located less than a mile from Great Barrington, it is close to everything the Berkshires are famous for;... View all property information
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    Location Information
    Great Barrington, Berkshires 01230
    From
    ₹15,945
    / Night
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    1 / 10
    5 of 5 stars (2) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 5
    travellers have booked this property
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Please note that this property is not winterized so it's not available this winter of 2012. I am winterizing this spring & the property will be available on a year around basis stating on 5/15/2013. Please go to VRBO.com listing #219964 to see my reviews, I am new to flipkey. Located in South... View all property information
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    Location Information
    Great Barrington, Berkshires 33304
    5 of 5 stars Reviewed 21 May 2013
    This was a perfect weekend for us. I am very picking when choosing a cabin rental because I want it to be "just right--" to fit into all of my ideal visions of the quintessential...
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    ₹11,991
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    1 / 12
    4 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    • Private Fishing...
    • Safe
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    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
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    Great Barrington, Berkshires 01236
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    ₹108,425
    / Week
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    1 / 10
    4 of 5 stars (1) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Internet Access
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • 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
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    Location Information
    Great Barrington, Berkshires 01230
    4 of 5 stars Reviewed 2 February 2015
    My cousin and I thoroughly enjoyed our stay. The house was cozy and very convenient for our needs. Having a laundry room just off the kitchen was great when we came back from the...
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    ₹29,658
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    1 / 33
    5 of 5 stars (3) Excellent
    4 Bedrooms / 3 Bathrooms / Sleeps 12
    traveller have booked this property
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Internet Access
    • Mountain Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    This sparkling, newly renovated cottage is for available vacation rental. A stunning sunrise & gorgeous view of the Berkshire Mountains. Conveniently located near many attractions. The house has been renovated by a contemporary designer. It has an open floor plan, making each room flow into... View all property information
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    Location Information
    Great Barrington, Berkshires 01230
    From
    ₹14,669
    / Night
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    1 / 14
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Fireplace
    • Internet Access
    • Mountain Views
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • 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. The Space: Quaint cottage with wood burning stove. Ideal base for enjoying... View all property information
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    Location Information
    Great Barrington, Berkshires 01230
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    ₹12,756
    / Night
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    1 / 15
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Sweet cozy house with plenty of room for large groups coming to enjoy the treasures of the Berkshires. Nestled behind Monument Mountain in Great Barrington. 4 bedrooms, 2.5 bathrooms, a spacious kitchen, living room, TV room, game room with pool/Ping-Pong table & two cars garage. Located within a... View all property information
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    Location Information
    Great Barrington, Berkshires 01230
    From
    ₹76,535
    / Week
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    1 / 16
    3 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Charming get-a-way in a friendly residential neighborhood in Great Barrington. Our home is sunny and bright, with an eat-in-kitchen, casual living room and dining area with beautiful picture windows, three comfortable bedrooms, and 1.5 bathrooms. Fully furnished with an eclectic mix of modern and... View all property information
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    Location Information
    Great Barrington, Berkshires 01230
    From
    ₹22,769
    / Night
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    1 / 23
    6 Bedrooms / 5 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This Elegant Luxury Estate offers 6000+ SF of Living Space on 13+ park-like, sunny acres located within only minutes from the downtown Great Barrington. This fantastic home offers 5 Bedrooms, 4.5 bathrooms, sweeping dual staircase ending with the magnificent open gallery, the kitchen offers the... View all property information
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    Location Information
    Great Barrington, Berkshires 01230