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Berkshires Cottages

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    Travelers to Berkshires are booking October dates now. Secure your vacation rental today, and have the perfect trip.
    13 Matching Rentals in BerkshiresView all 127 rentals
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    INTERIOR DESIGNERS BOTANICAL GARDENS1 / 30
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    Stockbridge Bowl Lake Beach Cottage near Tanglewood (1.8 miles away)1 / 17
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Family-friendly Cottage Near Lake, Tanglewood1 / 16
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Berkshires: Romantic Cottage with spectacular view1 / 18
    (24)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    It's a lovely first floor studio cottage with a kitchenette; very comfortable, well stocked, and beautifully decorated overlooking a gorgeous scene.
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    Amenities & Details
    • Parking
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    • DVD Player
    • Central Heating
    • Mountain Views
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 13, 2018
    First of all, the area where this house is is AMAZING. My husband and I have been coming to the Berkshires for years but we had never driven in this particular neighborhood. The...
    Reviewed August 3, 2018
    The picture is real (except we didn't see the rainbow). It's a lovely first floor studio cottage with a kitchenette; very comfortable, well stocked, and beautifully decorated...
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    About this property
    Berkshires: Romantic Berkshires Cottage with Stunning Views (Great Barrington) The Berkshires in spring, summer and fall are alive with beauty, and now is the time to plan your restoring getaway in this idyllic studio cottage with its glorious views of the rolling hills and verdant meadows.....
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    Location Information
    Great Barrington, Berkshires 01230
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Stone School Cottage1 / 10
    (17)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Along with the basic paper goods and toiletries, the cottage came with a cozy but functional kitchen (including microwave, Keurig, toaster), and helpful binders full of local restaurant and attraction info.
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    Amenities & Details
    • Air Conditioning
    • Mountain Views
    • Private Yard
    • Grill
    • Shared Yard
    • Outdoor Dining Area
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 20, 2018
    Lovely, memorable spot 20 mins from Williams College. The cottage is full of history, comfortable and well equipped. Even the one bathroom setup exceeded our expectations...
    Reviewed January 1, 2018
    this is a one of a kind experience. we loved it. Owners are super nice and were always promptly available. Location is perfect: a silent road, yet close to skiing, excellent...
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    About this property
    If you’ve driven by, you’ve wondered about the story of this beautiful stone building. Built in 1832 as a one-room schoolhouse – a function it served until 1950 -- this charming and historic building has been given new life as a vacation getaway. We are about 8 minutes away from Jiminy Peak and...
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    Location Information
    Lanesboro, Berkshires 01237
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    PanoramicView1000 sq ft Guest Quarters Berkshires1 / 16
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Mountain Views
    • Washer
    • Internet Access
    • Patio
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 30, 2015
    This is a lovely rental in the heart of the Berkshires. Each morning you wake up to aview of Jiminy Peak and the sounds of bird life. Tom and Susan are wonderful innkeepers and...
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    About this property
    Low long term rates. Call $2500/mo for 3 months. Free Electric Vehicle Charging Station! (240V 40A no J1772) Thanksgiving Special - Nov 24 - Dec 1 - $500 Christmas Special - Dec 20 - Dec 27 - $800 Ski Season Dec 1 - Mar 31 $8000 April $50/nt Summer Cultural May 26, 2014 - Seot 2, 2014 $7500 Summer...
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    Location Information
    Hancock, Berkshires 01237
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Lakefront New Marlborough Cottage - Mins to Skiing1 / 24
    (4)Excellent
    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 June 30, 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 June 22, 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 vacation rental cottage is sure to give you an experience in the Berkshires that you will never forget!...
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    Location Information
    New Marlborough, Berkshires 01230
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Romantic Berkshire Cottage on Storybook Estate1 / 10
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Balcony
    • Terrace
    • Cable/satellite TV
    • Outdoor Dining Area
    • Internet Access
    • DVD Player
    • Parking
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 19, 2017
    What a wonderful, magical place, heaven on earth! From the moment we were greeted warmly by Denise and entered our Tiny House, we knew this was such a special place.The sound of...
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    About this property
    Charming, One Bedroom Cottage, former sculpting studio on the Santarella Estate in Tyringham, MA. Known as the 'Silo Studio', there is a bedroom with queen bed upstairs, sitting room, wet bar with Micro/Fridge and bath downstairs. Fall asleep to sounds of babbling brook and views to pond and forest...
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    Location Information
    Tyringham, Berkshires 01264
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Berkshire Getaway1 / 7
    (8)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Housekeeping Included
    • Parking
    • Outdoor Dining Area
    • Grill
    • Porch
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 25, 2015
    Descriptions are accurate. The house and grounds are very well kept. Extremely clean especially bathroom and kitchen. It is located at the end of a hard pack dirt road with no...
    Reviewed August 24, 2015
    The minute we entered the cottage we felt at home. A perfect secluded, warm and cosy getaway. Our only sorrow was that we could only stay for one night. We prepared dinner in...
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    About this property
    Cozy cottage with complete privacy on 142 acres and borders Monroe State Forest. Cottage offers 2 bedrooms, 1 bathroom, large living room, eat in kitchen, deck with grill, TV and DVD. Hiking and biking is available right outside your door. The Dunbar Brook Trail boasts great hiking and a grove of...
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    Location Information
    North Adams, Berkshires 01247
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Lake House in Berkshires1 / 21
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Waterfront
    • DVD Player
    • Wi-Fi
    • Parking
    • Grill
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 4, 2017
    Robert was so thoughtful and courteous to make sure we had the best birthday weekend ever! He literally thought of everything such as bug spray, flash lights, birthday candles...
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    About this property
    Charming studio cottage on Windsor Lake, North Adams, MA. Great spot from which to explore MASS MoCa, attend Solid Sound or Fresh Grass, Clark Art Museum, Massachusetts College of Liberal Arts, Williamstown Theater Festival, Williams College, the Berkshires, and Southern Vermont. Hike, bike, swim...
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    Location Information
    North Adams, Berkshires 01247
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveler has booked this property
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    Amenities & Details
    • Wi-Fi
    • Parking
    • Mountain Views
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Great Barrington, Berkshires 01230
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Patio
    • Grill
    • Mountain Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    All New, renovated 400 sq. ft. cottage is located centrally in South Lee, / Stockbridge line. Only 1 mile from Stockbridge main street, nightly entertainment at the Red Lion's Den, close to everything, boutique shops, grocery stores, restaurants, and all Berkshire cultural attractions. Live...
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    Location Information
    Lee, Berkshires 01260
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • 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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    Location Information
    New Marlborough, Berkshires 01230
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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