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Holiday Rentals near The Well Restaurant + Bar

312 Main St, Great Barrington, Massachusetts 01230-1742
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    Don't let other travellers get your favourite Great Barrington area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 17 Rentals in Great Barrington
    Country Elegance in the Berkshires1 / 22
    (1)Excellent
    Great Barrington
    4.6 kilometres from The Well Restaurant + Bar
    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Berkshires: Romantic Cottage with spectacular view1 / 18
    (24)Excellent
    Great Barrington
    3.5 kilometres from The Well Restaurant + Bar
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Shaker Hill1 / 27
    (2)Average
    Great Barrington
    7.2 kilometres from The Well Restaurant + Bar
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Gem of the Berkshires, walk to downtown & lake.1 / 30
    (4)Excellent
    Great Barrington
    0.7 kilometres from The Well Restaurant + Bar
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Mountain Views
    • Patio
    • Grill
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 March 2018
    This home is a wonderfully appointed home, conveniently located just outside of town. It was perfect for our multiple family ski getaway. The owner is thorough in helping...
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    About this property
    This sparkling, newly renovated 3 floors house is for available vacation rental. A stunning sunrise & gorgeous view of the Berkshire Mountains. Conveniently located near many attractions, such as Tanglewood, Butternut ski, etc The house has an open floor plan, making each room flow into another....
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    Great Barrington, Berkshires
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Lakefront Berkshires Ski/Summer House, Great Views1 / 17
    (4)Very good
    Great Barrington
    6.5 kilometres from The Well Restaurant + Bar
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Mountain Views
    • Grill
    • DVD Player
    • Waterfront
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 November 2017
    The house was cozy. The lake was beautiful. The surrounding towns offer great restaurants. The host was very helpful.
    Reviewed 16 November 2017
    We rented this lovely home on the lake (or maybe it's a pond... Long Pond I think) last year and loved every minute of our visit. The house is well equipped and has all one...
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    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...
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    Great Barrington, Berkshires
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Cozy and clean in Gt Barrington- available for October1 / 14
    (1)Very good
    Great Barrington
    2.9 kilometres from The Well Restaurant + Bar
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Parking
    • Private Garden
    • Porch
    • Outdoor Dining Area
    • Washer
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Great Barrington, Berkshires
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Great Barrington
    4.8 kilometres from The Well Restaurant + Bar
    9 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Grill
    • Patio
    • Wi-Fi
    • Washer
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Great Barrington, Berkshires
    Holiday Rental House - 9 Bedrooms, 8 Bathrooms, Sleeps 16
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    The following rentals are within 15 kilometres of Great Barrington.
    RiverSong Suite In The Berkshires1 / 52
    (14)Excellent
    North Egremont
    6.5 kilometres from The Well Restaurant + Bar
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Patio
    • Air Conditioning
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 2018
    We eagerly anticipated our stay at RiverSong. Based on the plethora of five-star reviews we expected near-perfection. While we loved the atmosphere, fabulous comfortable bed...
    Reviewed 3 November 2017
    Riversong suite was wonderful, situated in a great location. Close to nearby restaurants and shops yet far from all the noise. Peaceful and quiet. A great place to renew...
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    About this property
    Located in the Berkshire mountains on more than 5 acres surrounded by 29 acres of conservation land. Featuring 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, resturaunts,...
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    North Egremont, Berkshires
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    North Egremont
    6.5 kilometres from The Well Restaurant + Bar
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Mountain Views
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our nearly new home we call RiverSong is on 5.5 acres surrounded by almost 30 more conservation land of meadow and farmland. The pristine Green River is right in our back yard with a wonderful swimming hole. Our Penthouse room is on the upper level of our home. A Bright and spacious king size...
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    North Egremont, Berkshires
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Waterfront Lake Buel Cottage - Open Year-Round!1 / 24
    (4)Excellent
    New Marlborough
    7.3 kilometres from The Well Restaurant + Bar
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Central Heating
    • Skiing: Property Is In A Ski Resort
    • Mountain Views
    • Waterfront
    • Patio
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 June 2018
    We had an excellent time with our two kids (7 and 8). The house is right on the lake with a great deck and amazing views. We used the kayaks every day. Location was great...
    Reviewed 22 June 2018
    Perfect location, perfect weather, beautiful view! Excellent owner, Carol, who responded to all our questions immediately. Would go back again in a minute.
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    About this property
    Let this serene lakefront Great Barrington area cottage in New Marlborough serve as your ultimate home-away-from-home! Featuring 2 bedrooms, 1-bathroom, and enough room to sleep 4 guests, this year-round vacation rental cottage is sure to give you an experience in the Berkshires that you will never...
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    New Marlborough, Berkshires
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Sheffield
    7.0 kilometres from The Well Restaurant + Bar
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Balcony
    • Air Conditioning
    • Parking
    • Mountain Views
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located along the Appalachian trail and 3 miles to Great Barrington, this designer home is central to all the Berkshires has to offer, not to mention being 35 minutes to Hudson you are really in the center of of it all. This completely separate designer home is located on the 2nd and 3rd floors...
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    Sheffield, Berkshires
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    The Smith Farm Homestead1 / 12
    (6)Excellent
    Alford
    6.3 kilometres from The Well Restaurant + Bar
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Hot Tub
    • Mountain Views
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 October 2018
    This was a perfect place for a bit of R & R. Friendly owners and luxurious room that was clean and comfortable. The home has a historical atmosphere in a beautiful country...
    Reviewed 4 February 2017
    Cozy and pretty room and bathroom suite that I shared with my teenaged daughter. Susan is very welcoming and friendly. We loved our stay here and would return!
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    About this property
    The Smith Homestead in Alford Massachusetts has been homesteaded and farmed by our family for the past two centuries. Located on one of the nicest settings in the Berkshires, with 30 acres of fields and woods, and the crystal clear Alford Brook running through, we are central to all the cultural...
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    Alford, Berkshires
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Newly Renovated Colonial on the River! Sleeps 5-61 / 20
    (1)Excellent
    Stockbridge
    8.0 kilometres from The Well Restaurant + Bar
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Internet Access
    • Patio
    • Waterfront
    • Central Heating
    • Cable/satellite TV
    • Porch
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Blue House on the Bend Newly renovated historic eyebrow colonial located on an idyllic bend of the Housatonic river comfortably accommodates 5 or 6 people. Built around 1820, the Blue House on the Bend has been updated and outfitted for modern day convenience but retains its charm and unique...
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    Stockbridge, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    North Egremont
    6.0 kilometres from The Well Restaurant + Bar
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Private Outdoor Pool (Unheated)
    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Book a one-of-a-kind stay in this 5-bedroom, 4.5-bathroom vacation rental home in South Egremont. Built from the bones of a 15th-century British barn, this 4,000-square-foot home for 10 is one of the oldest structures in Massachusetts! Whether you were drawn to the Berkshires by the natural beauty...
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    North Egremont, Berkshires
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    New Marlborough
    7.3 kilometres from The Well Restaurant + Bar
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bring your loved one along on a Berkshires getaway in this 1-bedroom, 1-bathroom vacation rental cottage in New Marlborough that sleeps 2. Nestled under the pine trees on the edge of Lake Buel, you'll have unbeatable views of the picturesque landscape, framed by the large windows throughout the...
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    New Marlborough, Berkshires
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    West Stockbridge
    7.8 kilometres from The Well Restaurant + Bar
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Patio
    • Washer
    • Balcony
    • Air Conditioning
    • Housekeeping Included
    • Mountain Views
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We offer two bedrooms accessible via a private staircase in our recently renovated Victorian farm house located on two beautifully landscaped acres with seasonal gardens and adjoining woods and fields. Each bedroom sleeps 2; they can be booked individually or together at $105/bedroom/night. We...
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    West Stockbridge, Berkshires
    Private Room - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Monterey
    6.9 kilometres from The Well Restaurant + Bar
    Studio, 2 Bathrooms, Sleeps 7 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You'll love our hand-hewn post & beam beauty on 13 acres in the Berkshire Mountains of Western Mass located near the Monterey/Great Barrington line, close to everything. Great for summer and winter ski season. Rich in both outdoor and cultural attractions, shopping and antiquing. Located adjacent...
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    Location Information
    Monterey, Berkshires
    Holiday Rental House - 2 Bathrooms, Sleeps 7
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