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Berkshires Cheap Rentals

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    Travelers to Berkshires are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    35 Matching Rentals in BerkshiresView all 143 rentals
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    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    Berkshire House Share-The Blue Room1 / 10
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
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    • Mountain Views
    • Outdoor Dining Area
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    the garden room is a small room with a full sized bed. everything is floral, even the closet walls. it 's a sweet room with even a wood stove. it has an entrance to the courtyard just outside in the hall, the bath may be shared depending on the situation. bath has shower and lovely old sink. bath...
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    Lee, Berkshires 01238
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Sauna
    • Hot Tub
    • Air Conditioning
    • Shared Indoor Pool
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled among the Berkshire Mountains, you will find a true New England treasure; The Wyndham Bentley Brook. Located a mere 200 feet away from the premier Jimmy Peak Mountain Resort puts you in position to take part in the area’s best skiing & snowboarding. After a full day on the slopes, warm up...
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    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • DVD Player
    • Air Conditioning
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    • Grill
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The town of Hancock is off the beaten path near the Taconic Mountains, which are part of the Appalachians. Hancock is 14 miles northwest of Pittsfield, MA, and 28 miles east of Albany, NY. Bentley Brook is tucked away in a peaceful rural setting with a cozy lobby fireplace and pristine location. It...
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    Hancock, Berkshires 01237
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    • Wi-Fi
    • Grill
    • Air Conditioning
    • Parking
    • Hot Tub
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The town of Hancock is off the beaten path near the Taconic Mountains, which are part of the Appalachians. Hancock is 14 miles northwest of Pittsfield, MA, and 28 miles east of Albany, NY. Bentley Brook is tucked away in a peaceful rural setting with a cozy lobby fireplace and pristine location. It...
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    Hancock, Berkshires 01237
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    • DVD Player
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Grill
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bentley Brook The town of Hancock is off the beaten path near the Taconic Mountains, which are part of the Appalachians. Hancock is 14 miles northwest of Pittsfield, MA, and 28 miles east of Albany, NY. Bentley Brook is tucked away in a peaceful rural setting with a cozy lobby fireplace and...
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    Hancock, Berkshires 01237
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bentley Brook The town of Hancock is off the beaten path near the Taconic Mountains, which are part of the Appalachians. Hancock is 14 miles northwest of Pittsfield, MA, and 28 miles east of Albany, NY. Bentley Brook is tucked away in a peaceful rural setting with a cozy lobby fireplace and...
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    Hancock, Berkshires 01237
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
    • DVD Player
    • Wi-Fi
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The town of Hancock is off the beaten path near the Taconic Mountains, which are part of the Appalachians. Hancock is 14 miles northwest of Pittsfield, MA, and 28 miles east of Albany, NY. Bentley Brook is tucked away in a peaceful rural setting with a cozy lobby fireplace and pristine location. It...
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    Hancock, Berkshires 01237
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Parking
    • Grill
    • DVD Player
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The town of Hancock is off the beaten path near the Taconic Mountains, which are part of the Appalachians. Hancock is 14 miles northwest of Pittsfield, MA, and 28 miles east of Albany, NY. Bentley Brook is tucked away in a peaceful rural setting with a cozy lobby fireplace and pristine location. It...
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    Hancock, Berkshires 01237
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The town of Hancock is off the beaten path near the Taconic Mountains, which are part of the Appalachians. Hancock is 14 miles northwest of Pittsfield, MA, and 28 miles east of Albany, NY. Bentley Brook is tucked away in a peaceful rural setting with a cozy lobby fireplace and pristine location. It...
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    Hancock, Berkshires 01237
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • Parking
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
    • Hot Tub
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The town of Hancock is off the beaten path near the Taconic Mountains, which are part of the Appalachians. Hancock is 14 miles northwest of Pittsfield, MA, and 28 miles east of Albany, NY. Bentley Brook is tucked away in a peaceful rural setting with a cozy lobby fireplace and pristine location. It...
    View all property information
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    Hancock, Berkshires 01237
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Grill
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The town of Hancock is off the beaten path near the Taconic Mountains, which are part of the Appalachians. Hancock is 14 miles northwest of Pittsfield, MA, and 28 miles east of Albany, NY. Bentley Brook is tucked away in a peaceful rural setting with a cozy lobby fireplace and pristine location. It...
    View all property information
    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Hot Tub
    • DVD Player
    • Grill
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The town of Hancock is off the beaten path near the Taconic Mountains, which are part of the Appalachians. Hancock is 14 miles northwest of Pittsfield, MA, and 28 miles east of Albany, NY. Bentley Brook is tucked away in a peaceful rural setting with a cozy lobby fireplace and pristine location. It...
    View all property information
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    Hancock, Berkshires 01237
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Washer
    • Central Heating
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The guest suite is within 'Keyes House,' a quintessential 19th century Greek Revival colonial. It is conveniently located in a small, bucolic village in Southern Berkshire County that is on the National Register of Historic Districts. The entire home, including the two-room suite, has been...
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    New Marlborough, Berkshires 01230
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Sauna
    • Wi-Fi
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Complete your Berkshires retreat with a stay in the spacious Studios, perfect for romantic couples and small families. Suites feature plush bedding, additional sleeper sofa and fully equipped kitchen for all your dining needs. Minimum age to check in is 21 Daily housekeeping is not included and...
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    Hancock, Berkshires 01237
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Whitman Woods - A Berkshire Vacation1 / 26
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Yard
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    Reviewed August 16, 2018
    Whitman Woods is an amazing house for families to get away from it all. We did an overnight in this house while visiting Pittsfield to watch a couple musicals. The house is...
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    About this property
    The vacation house at Whitman Woods offers privacy with proximity to excellent skiing at Jiminy Peak and to many cultural attractions of the Berkshires, 'America's Premier Cultural Resort', including Williamstown Theater Festival, the Clark Art Museum, Hancock Shaker Village and Tanglewood. For...
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    Hancock, Berkshires 01237
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Washer
    • Air Conditioning
    • DVD Player
    • Mountain Views
    • Grill
    • Sauna
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Luxury Condo in Beaver Pond, Hancock, Mass. Three bedrooms, loft, 2 baths, living room, kitchen with dining area, deck w/grill. Near Clark Art Museum, MassMoca. Williams College with schedule of sports open to the public: swimming, tennis, squash, basketball, skating and fitness room. Indoor...
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    Hancock, Berkshires 01237
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cozy & Modern Home -mins from Tanglewood & Kripalu1 / 8
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 18, 2013
    We stayed at this home in Housatonic, which is part of Great Barrington, the Smithsonian pic for best small town in the USA. I hope you all don't however as one of the best...
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    About this property
    Cozy and modern two bedroom and one bath vacation home with lake nearby Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This luxury home can sleep up to 6 people and has lake access nearby. Enjoy a nice cup of hot chocolate by the fireplace in the living...
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    West Stockbridge, Berkshires 01266
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    1 Bedroom, 2 Bathrooms, Sleeps 8 Quick View
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    • Housekeeping Included
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    • Mountain Views
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    I have a two bedroom downstairs apartment and a three bedroom upstairs apartment (all of the rooms are available to rent). I also rent out the full apartments but I also rent out rooms (please ask for information). The house is located on a dead end street with a huge wooded backyard that...
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    North Adams, Berkshires 01247
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 8
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    Lake House in Berkshires1 / 21
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Waterfront
    • DVD Player
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    • Mountain Views
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    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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    North Adams, Berkshires 01247
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Balcony
    • Hot Tub
    • Parking
    • Wi-Fi
    • Grill
    • Terrace
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the beautiful Berkshires. Watch the horses roam. Have a guided trail ride (additional fee) or have a camp fire only feet away from the horses. Within steps from your accommodations, enjoy the largest recreational lake in Massachusetts. Bring your boat or jetski. Or use our row boat. Go...
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    East Otis, Berkshires 01029
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    1 Bedroom, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Grill
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Surround yourself with the natural beauty of Massachusetts at Bentley Brook. Situated at the bottom of Jiminy Peak in the stunning Berkshires, Bentley Brook is the ski enthusiast dream come true. Ski out your door and straight to the resorts ski lift. Spend a day out on the world class trails, then...
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    Hancock, Berkshires 01237
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bentley Brook Surround yourself with the natural beauty of Massachusetts at Bentley Brook. Situated at the bottom of Jiminy Peak in the stunning Berkshires, Bentley Brook is the ski enthusiast dream come true. Ski out your door and straight to the resorts ski lift. Spend a day out on the world...
    View all property information
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    Hancock, Berkshires 01237
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Hot Tub
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bentley Brook Surround yourself with the natural beauty of Massachusetts at Bentley Brook. Situated at the bottom of Jiminy Peak in the stunning Berkshires, Bentley Brook is the ski enthusiast dream come true. Ski out your door and straight to the resorts ski lift. Spend a day out on the world...
    View all property information
    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Hot Tub
    • Air Conditioning
    • Grill
    • Parking
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bentley Brook Surround yourself with the natural beauty of Massachusetts at Bentley Brook. Situated at the bottom of Jiminy Peak in the stunning Berkshires, Bentley Brook is the ski enthusiast dream come true. Ski out your door and straight to the resorts ski lift. Spend a day out on the world...
    View all property information
    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Hot Tub
    • Grill
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bentley Brook Surround yourself with the natural beauty of Massachusetts at Bentley Brook. Situated at the bottom of Jiminy Peak in the stunning Berkshires, Bentley Brook is the ski enthusiast dream come true. Ski out your door and straight to the resorts ski lift. Spend a day out on the world...
    View all property information
    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • DVD Player
    • Hot Tub
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bentley Brook Surround yourself with the natural beauty of Massachusetts at Bentley Brook. Situated at the bottom of Jiminy Peak in the stunning Berkshires, Bentley Brook is the ski enthusiast dream come true. Ski out your door and straight to the resorts ski lift. Spend a day out on the world...
    View all property information
    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Parking
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bentley Brook Surround yourself with the natural beauty of Massachusetts at Bentley Brook. Situated at the bottom of Jiminy Peak in the stunning Berkshires, Bentley Brook is the ski enthusiast dream come true. Ski out your door and straight to the resorts ski lift. Spend a day out on the world...
    View all property information
    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 2 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
    • Grill
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bentley Brook Surround yourself with the natural beauty of Massachusetts at Bentley Brook. Situated at the bottom of Jiminy Peak in the stunning Berkshires, Bentley Brook is the ski enthusiast dream come true. Ski out your door and straight to the resorts ski lift. Spend a day out on the world...
    View all property information
    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bentley Brook Surround yourself with the natural beauty of Massachusetts at Bentley Brook. Situated at the bottom of Jiminy Peak in the stunning Berkshires, Bentley Brook is the ski enthusiast dream come true. Ski out your door and straight to the resorts ski lift. Spend a day out on the world...
    View all property information
    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 2 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Parking
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bentley Brook Surround yourself with the natural beauty of Massachusetts at Bentley Brook. Situated at the bottom of Jiminy Peak in the stunning Berkshires, Bentley Brook is the ski enthusiast dream come true. Ski out your door and straight to the resorts ski lift. Spend a day out on the world...
    View all property information
    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 1400 square foot, three bedroom home has all amenities including washer and dryer in basement. Electric heat and oven. Front porch and back deck. First floor is open floor plan with kitchen, dining area and living room flowing from one to the other. Skylights in the living/dining area and...
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    Lee, Berkshires 01240
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Lakefront Berkshires Ski/Summer House, Great Views1 / 17
    (4)Very good
    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 November 16, 2017
    The house was cozy. The lake was beautiful. The surrounding towns offer great restaurants. The host was very helpful.
    Reviewed November 16, 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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    Location Information
    Great Barrington, Berkshires 01236
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    November
    33° 18°
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