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Elder Access Holiday Rentals in Berkshires

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    Travellers to Berkshires are booking August dates now. Secure your holiday rental today, and have the perfect trip.
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    $333
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    1 / 19
    5 of 5 stars (15) Excellent
    West Stockbridge
    5 Bedrooms / 2 Bathrooms / Sleeps 12
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    $366
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    1 / 32
    5 of 5 stars (1) Excellent
    Becket
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    $173
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    1 / 10
    5 of 5 stars (1) Excellent
    North Adams
    2 Bedrooms / 1 Bathroom / Sleeps 8
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    $193
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    1 / 16
    5 of 5 stars (1) Excellent
    Hancock
    1 Bedroom / 1 Bathroom / Sleeps 6
    travellers have booked this property
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    Amenities & Details
    • Mountain Views
    • Stereo System
    • Internet Access
    • Deck
    • Satellite TV
    • Fireplace
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    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... View all property information
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    Location Information
    Hancock, Berkshires 01237
    5 of 5 stars Reviewed 17 October 2014
    This property is perfect for people with pets. Serene setting with a gorgeous view. The hosts, Tom and Susan, were gracious and very helpful. Highly recommended if your travels...
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    $305
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    1 / 4
    4 of 5 stars (1) Very good
    Hancock
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    travellers have booked this property
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    Amenities & Details
    • Satellite TV
    • Mountain Views
    • Internet Access
    • DVD Player
    • Deck
    • Air Conditioning
    • Dryer
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Cozy ranch home 3 miles away from Jiminy Peak Ski Resort. Near MASS MOCA, Clark Art Institute, Williams College Contemperary Museum of Art, Williamstown Theatre Festival, Tanglewood, shopping, golf courses. Wrap around deck with beautiful mountain views. Family room with full wet bar & flat screen... View all property information
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    Hancock, Berkshires 01237
    4 of 5 stars Reviewed 12 August 2013
    Aside from the excessive amount of men's shirts in the closets (closets and drawers had not been emptied so storage space was minimal), the full trash bins and dirty dishes...
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    1 / 36
    5 of 5 stars (114) Excellent
    Charlemont
    1 Bedroom / 1 Bathroom / Sleeps 4
    travellers have booked this property
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    Amenities & Details
    • Internet Access
    • Washer
    • Air Conditioning
    • Dryer
    • Satellite TV
    • Stereo System
    • Deck
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Discover Cavalier Cottage B&B, a pet-friendly home away from your home and an attractive alternative to conventional hotels, motels and B&B's. We warmly welcome visitors who come to this beautiful and diverse area of Western Massachusetts with or without their companion animals. Since opening... View all property information
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    Location Information
    Charlemont, Berkshires 01339
    5 of 5 stars Reviewed 5 July 2015
    The Cavalier Cottage is really perfect for a couple of small family getaway. We brought our daschund and were heart-warmed by the doggie treats and baggies left for us to use...
    5 of 5 stars Reviewed 26 June 2015
    The cottage was the perfect little place for us and our fur babies to stay while visiting Eddie's Wheels. Great location, so peaceful among the beauty of nature. Very clean, close...
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    $265
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    1 / 10
    5 of 5 stars (13) Excellent
    Great Barrington
    1 Bedroom / 1 Bathroom / Sleeps 3
    travellers have booked this property
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    Amenities & Details
    • Boat Available
    • Satellite TV
    • Shared Outdoor Pool...
    • Stereo System
    • DVD Player
    • Central Heating
    • Mountain Views
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    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..... View all property information
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    Location Information
    Great Barrington, Berkshires 01230
    5 of 5 stars Reviewed 28 June 2015
    Magnificent view, hosts were lovely, very generous, the pool was divine. Can't give enough accolades-if you get a chance, don't walk-run there.
    5 of 5 stars Reviewed 18 August 2014
    We stayed at the cottage for three days, and it was just as lovely as advertised. The space is perfect for a couple, with a comfortable queen bed and well-equipped kitchen...
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    1 / 32
    5 of 5 stars (2) Excellent
    Stockbridge
    4 Bedrooms / 4 Bathrooms / Sleeps 12
    travellers have booked this property
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Private Fishing...
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Stereo System
    • Sauna
    • Mountain Views
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    We call this house ‘South Sedgwick’ because of its location on a piece of land formerly used by the Sedgwick family for picnicking–an ideal spot for relaxation with stunning views of Monument Mountain and Ice Glen. The house is newly constructed with ash hardwood floors, custom white pine trim and... View all property information
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    Location Information
    Stockbridge, Berkshires 01262
    5 of 5 stars Reviewed 4 December 2014
    What a great place! Teva was wonderful to work with, communication was incredible, and he is very welcoming. The house was spacious, very comfortable with 9 people! Teva came by...
    5 of 5 stars Reviewed 19 July 2014
    Our family of 5 rented this home over July 4th weekend and we couldn't have been more pleased. The home has just been newly renovated, is very tastefully appointed and looks and...
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    $479
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    1 / 30
    5 of 5 stars (3) Excellent
    North Adams
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • DVD Player
    • Central Heating
    • Satellite TV
    • Deck
    • Stereo System
    • Fireplace
    • Playground
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Spectacular views are yours from this 2000 square foot Chalet Lodge located on the 50 acre Rose and Goat Retreat on the top of beautiful Florida Mountain in the Berkshires in Western Massachusetts. Enjoy cozy evenings in front of the massive stone fireplace after a day of enjoying all that the the... View all property information
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    Location Information
    North Adams, Berkshires 01247
    5 of 5 stars Reviewed 25 August 2014
    I booked the Rose & Goat Retreat for my sister's Bachelorette Weekend in the Berkshires! Not only was it the perfect location because it was only 11 miles away from our zip lining...
    5 of 5 stars Reviewed 13 March 2014
    This place is an absolutely gorgeous lodge, with an incredible view of the Berkshires. Margo was very hospitable and took great care of all of our needs. The pictures don't do...
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    1 / 5
    Granville
    5 Bedrooms / 3 Bathrooms / Sleeps 12
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Water Views
    • TV
    • Waterfront
    • DVD Player
    • Balcony
    • Central Heating
    • Deck
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    4 Bedrooms, 3 Baths, 3 Guest Rooms, Open Floor Plan Kitchen, Living, Dining 4 Bedrooms, 3 Baths, 3 Guest Rooms, Open Floor Plan Kitchen, Living, Dining Lakefront, 4 bedrooms, 3 baths, 3 guest rooms, open floor plan with kitchen, living and dining areas, family room, sports room, deck, two... View all property information
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    Location Information
    Granville, Berkshires 01034
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    $353
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    1 / 21
    Monterey
    5 Bedrooms / 3 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Amenities & Details
    • Mountain Views
    • Water Park Nearby
    • Central Heating
    • Watersports Nearby
    • TV
    • DVD Player
    • Playground
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This is a beautiful Berkshire, post and beam private house nestled in the woods just off the Appalachian trail. Set on one of the Berkshires most coveted roads close to fresh water swimming in Lake Garfield, boating, fishing, classical outdoor concerts at Tanglewood & Skiing are all close by. The... View all property information
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    Location Information
    Monterey, Berkshires 01245
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    $300
    / Night
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    1 / 16
    Hancock
    2 Bedrooms / 2 Bathrooms / Sleeps 8
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Hot Tub
    • Sauna
    • Internet Access
    • Satellite TV
    • Shared Indoor Pool
    • Air Conditioning
    • Mountain Views
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Bentley Brook is a ski in/ski out resort located at the base of Jiminy Peak ski resort. On-site Amenities Include: Heated Indoor/Outdoor Pool (year round), 3 hot tubs, 'Get out & Play ' children's program, 3 tennis courts, game room, exercise equipment, sauna, theater with nightly movies.. At... View all property information
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    Location Information
    Hancock, Berkshires 01237
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    $1,066
    / Week
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    1 / 12
    Charlemont
    1 Bedroom / 1 Bathroom / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Stereo System
    • Mountain Views
    • Washer
    • Dryer
    • DVD Player
    • Central Heating
    • Wi-Fi
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    If you're looking for gorgeous mountain views in a peaceful setting, come stay in Comsomore Cottage - a mountainside log cabin located on the 50 acre mountain top estate, the Rose and Goat Retreat in the beautiful Berkshires, USA. Ideal for someone who wants to make this their home for a little... View all property information
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    Location Information
    Charlemont, Berkshires 01247
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    $333
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    1 / 16
    5 of 5 stars (1) Excellent
    North Adams
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Central Heating
    • TV
    • Waterfront
    • Mountain Views
    • Deck
    • Private Fishing...
    • Boat Available
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Windsor Cottage is a beautiful, newly renovated lakeside retreat located on Windsor Lake in North Adams, MA. where you can enjoy your own private water access from your front lawn. You will feel like you are in the middle of the forest, yet you are in walking distance to the town, Mass MoCA and... View all property information
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    Location Information
    North Adams, Berkshires 01247
    5 of 5 stars Reviewed 17 August 2014
    The cottage is well located, seemingly remote, but with nearby access to local attractions and restaurants. I enjoyed sitting on the deck, looking out over the water in the...
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    1 / 19
    4.5 of 5 stars (23) Very good
    Stockbridge
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (23) Make Enquiry
    Amenities & Details
    • Satellite TV
    • Patio
    • Mountain Views
    • Deck
    • Air Conditioning
    • Grill
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    The Cottage, in picturesque Stockbridge, has the PERFECT location -- minutes from Main Street Lenox, Main Street Stockbridge, The Norman Rockwell Museum, Berkshire Botanical Gardens, Tanglewood Music Festival, The Shrine of the Divine Mercy at the Congregation of Marians, shops, theaters, hiking... View all property information
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    Location Information
    Stockbridge, Berkshires 01262
    5 of 5 stars Reviewed 17 May 2015
    The Cottage has 2 suites and my husband and I have stayed in both. In 2013 we used one suite for our honeymoon and enjoyed it so much we returned April of 2014 and had the same...
    5 of 5 stars Reviewed 5 November 2014
    Beautiful grounds, quiet, clean. Owner is available at all times. Close to all area attractions. Great Barrington, Stockbridge, West Stockbridge, Lennox are all within a 10 min...
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    1 / 5
    5 of 5 stars (1) Excellent
    Hancock
    2 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Satellite TV
    • Mountain Views
    • Hot Tub
    • Game Room
    • Wi-Fi
    • Air Conditioning
    • Shared Indoor Pool
    • Staffed Property
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Fantastic Value at over 50% off the retail rates! Great Fall Season pricing of only $299 for each entire week's stay! No other fees due! We own this timeshare and can't use it this year! 2 bedroom, 2 bath, sleeps 8 Fully furnished with cooking utensils, linens and towels for up to 6 people.... View all property information
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    Location Information
    Hancock, Berkshires 01237
    5 of 5 stars Reviewed 17 February 2015
    Didn't go late enough for the Fall Foliage, but even as the leaves were just turning this was a lovely resort to visit. We go to the Highlands of Scotland every other year where...
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    $666
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    1 / 15
    Tyringham
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Central Heating
    • Satellite TV
    • Staffed Property
    • Wi-Fi
    • DVD Player
    • Watersports Nearby
    • Mountain Views
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Located on the Santarella Estate, an historic site located in the the Massachussetts' Berkshires. The colonial home is the former residence of sculptor Sir Henry Hudson Kitson. The estate includes the landmark, iconic storybook style 'Gingerbread House,' designed by Kitson to look like an English... View all property information
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    Location Information
    Tyringham, Berkshires 01264
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    $999
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    1 / 7
    Lee
    5 Bedrooms / 5 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    --Brand new 3400 sq ft Lee home in a private lake community, Berkshires --Situated on 4 wooded acres on a quiet country road --Pristine home features two master bedroom suites plus 3 additional bedrooms, 5 bathrooms --Spacious living room with vaulted ceiling & skylights --Fully equipped kitchen,... View all property information
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    Location Information
    Lee, Berkshires 01238
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    $266
    / Night
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    1 / 11
    3 of 5 stars (1) Average
    Stockbridge
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Stereo System
    • Central Heating
    • Internet Access
    • DVD Player
    • Satellite TV
    • Mountain Views
    • Waterfront
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    3-bedroom home on lake, near Tanglewood. 2 baths, den, screened porch, large yard. View all property information
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    Location Information
    Stockbridge, Berkshires 01262
    3 of 5 stars Reviewed 31 July 2014
    Nice house but tired bathrooms and kitchen. One great bedroom, two so so. Hot one nite and needed non existing a/c. Great screened porch with view of water. Canoe was a plus...
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    1 / 18
    Hinsdale
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    travellers have booked this property
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    Amenities & Details
    • DVD Player
    • Water Views
    • Washer
    • Deck
    • Dryer
    • TV
    • Central Heating
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    The best place in the world to watch the sunset! Set up high on a hill and nestled amidst the pine trees, this four year old, private and spacious contemporary home overlooks Lake Ashmere (across the road) in Hindsdale. The great room with cathedral ceilings and a wall of windows overlooking the... View all property information
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    Location Information
    Hinsdale, Berkshires 01235
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    $400
    / Night
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    1 / 23
    Great Barrington
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Washer
    • DVD Player
    • Mountain Views
    • Stereo System
    • Internet Access
    • Fireplace
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Beautifully furnished, updated 3,000 square foot house. 3 bedrooms, 2 full baths; large sun room with great windows and sky-lights, comfortable seating area for 6 plus cafe table; dining room with table for 6 to 8 people; reading room with a wood-burning stove; living room with a fireplace;... View all property information
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    Location Information
    Great Barrington, Berkshires 01230
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    $233
    / Night
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    1 / 13
    4.5 of 5 stars (13) Very good
    Monterey
    3 Bedrooms / 2 Bathrooms / Sleeps 7
    traveller have booked this property
    Overview Reviews (13) Make Enquiry
    Amenities & Details
    • Mountain Views
    • Playground
    • Water Views
    • Satellite TV
    • Internet Access
    • Waterfront
    • Hot Tub
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Charming house with the feeling of a cottage, set on a knoll with adjacent cathedral-like pine forest. ** Stone fireplace, woodstove, beautiful kitchen with modern appliances (gas stove, microwave, refrigerator with water/ice dispenser, dishwasher, breadmaker, crockpot, blender, etc.) **... View all property information
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    Location Information
    Monterey, Berkshires 01245 0933
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    $533
    / Night
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    1 / 24
    Lenox
    4 Bedrooms / 2 Bathrooms / Sleeps 10
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Sauna
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Playground
    • Shared Indoor Pool
    • Mountain Views
    • Shared Tennis Court
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    220+ Acres W\ Tennis Cts, Indoor / Outdoor Pool, Canoe, Fishing Boat, Hot Tub. New first time rental of 4 BR, 2BA, Cape Cod style, sleeps 10-12. New fully equipped kitchen w/ center island, indoor and outdoor barbecues, wine cooler, 2 fireplaces, large deck with 8 person hot tub and super seating... View all property information
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    Location Information
    Lenox, Berkshires 01240
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    $266
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    1 / 11
    Great Barrington
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • DVD Player
    • Grill
    • Satellite TV
    • Linens Provided
    • Cooker
    • Refrigerator
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    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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    Location Information
    Great Barrington, Berkshires 01237
    From
    $466
    / Night
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    1 / 11
    5 of 5 stars (1) Excellent
    Great Barrington
    4 Bedrooms / 2 Bathrooms / Sleeps 9
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Hot Tub
    • Washer
    • Internet Access
    • Satellite TV
    • Stereo System
    • Fireplace
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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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    Location Information
    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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    $400
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    1 / 9
    Housatonic
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Central Heating
    • Stereo System
    • Dryer
    • Refrigerator
    • Washer
    • DVD Player
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This house is a perfect family retreat in the Berkshires. Nestled in the Village of Housatonic you will be centrally located to all Berkshire attractions. Less that ten minutes from skiing and Tanglewood, as well as the shops and restaurants of Stockbridge, Lenox, and Great Barrington, this is... View all property information
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    Housatonic, Berkshires 01236
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    $252
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    1 / 16
    4 of 5 stars (1) Very good
    Hancock
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Central Heating
    • Hot Tub
    • Internet Access
    • Shared Indoor Pool
    • DVD Player
    • Sauna
    • Satellite TV
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    A fully furnished and nicely appointed 2br/2ba suite. There's a full kitchen, living room with sofa sleeper, king bed in master bedroom, 2nd bedroom has either a king bed or two queen size beds(varies), washer/dryer, private balcony with mountain or valley views. Everything you need on your... View all property information
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    Hancock, Berkshires 01237
    4 of 5 stars Reviewed 26 October 2014
    Lovely place with pool, spa, gym, and movie theater. Units are a bit noisy between floors but otherwise nice and quiet. We had the unfortunate experience of having three small...
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    $233
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    4.5 of 5 stars (15) Very good
    New Ashford
    4 Bedrooms / 3 Bathrooms / Sleeps 7
    Overview Reviews (15) Make Enquiry
    Amenities & Details
    • Wi-Fi
    • Private Fishing...
    • Central Heating
    • Mountain Views
    • Water Views
    • Housekeeping...
    • Satellite TV
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    The Berkshire Gorge House sits beside the Green River above a turbulent set of cascades, on the western slopes of Mt. Greylock. This 5-bedroom house was built in 1910 by New England's finest craftsmen. It has been recently remodeled and is offered for rent. The house offers a new kitchen with gas... View all property information
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    New Ashford, Berkshires 01237
    5 of 5 stars Reviewed 4 January 2015
    I am kicking myself that I didn't invite my brother, sister-in-law and their small kids to come with us on this trip. There sure was plenty of room! Right when you enter the...
    5 of 5 stars Reviewed 2 December 2014
    The house was everything we expected. Right from the beginning there was clear communication between us, the owner and the property manager. The booking process was easy. Checking...
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    $186
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    Hinsdale
    3 Bedrooms / 2 Bathrooms / Sleeps 7
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Central Heating
    • TV
    • DVD Player
    • Stereo System
    • Internet Access
    • Deck
    • Washer
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Located on 19 acres of forest and a creek, mixing modern and traditional with a charming two story wall of windows overlooking a back deck. This comfortable furnished home has two bedrooms with an additional open loft area for a third bedroom, two baths, all hardwood floors, and contains a large... View all property information
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    Location Information
    Hinsdale, Berkshires 01235
    From
    $575
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    Charlemont
    5 Bedrooms / 3 Bathrooms / Sleeps 14
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Water Views
    • Garage
    • Mountain Views
    • Central Heating
    • Grill
    • Internet Access
    • TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Hawk Mountain Lodge offers a year-round New England vacation experience! Enjoy comfortable accommodations conveniently located in Charlemont in the northern Berkshires, just 2.5 hours from Boston and 3.5 to 4 hours from New York City. Overlooking the Deerfield River Valley and Berkshire East Ski... View all property information
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    Location Information
    Charlemont, Berkshires 01339
    From
    $400
    / Night
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    1 / 18
    4.5 of 5 stars (9) Very good
    Hancock
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (9) Make Enquiry
    Amenities & Details
    • Washer
    • Air Conditioning
    • Satellite TV
    • Dryer
    • Internet Access
    • Hot Tub
    • Sauna
    • Shared Indoor Pool
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    On-site Amenities Include: Heated Indoor/Outdoor Pool (year round), Alpine Slide (warmer months), Berkshire Express Chairlift to Summit Lodge during ski season. The Berkshire Express provides scenic rides during warmer months. Bentley Brook is situated Slope Side for SKI/IN - SKI/OUT all winter... View all property information
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    Location Information
    Hancock, Berkshires 01237
    5 of 5 stars Reviewed 24 March 2015
    This is such a great property. We had a one bedroom unit which was still sufficient for 2 adults and 3 teens. Gorgeous large double bedroom with full bath and murphy bed and...
    4 of 5 stars Reviewed 27 January 2015
    Always a great trip for Friends and family. Easy quick park and party. They have a movie theater activities for kids all day long indoor outdoor swimming pool hot cider coffee and...
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    $133
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    5 of 5 stars (1) Excellent
    Pittsfield
    1 Bedroom / 1 Bathroom / Sleeps 5
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Satellite TV
    • Shared Indoor Pool
    • Air Conditioning
    • DVD Player
    • Hot Tub
    • Internet Access
    • Stereo System
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    A Fully-Furnished Extended Stay property in the Berkshires. Located across the street from the Colonial Theatre and within minutes of most Berkshire County attractions. Each spacious, efficiency (condo-style) single bedroom apartment includes living room, kitchen with full size appliances,... View all property information
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    Pittsfield, Berkshires 01201
    5 of 5 stars Reviewed 3 July 2013
    WOW, this place was very nice! What you get is a place with a five minute walk from downtown, well kept buidlings and grounds, excellent floor plans, new furniture, modern...
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    $333
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    1 / 19
    Great Barrington
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Stereo System
    • Satellite TV
    • Washer
    • Mountain Views
    • Deck
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • ?
    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
    $400
    / Night
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    1 / 16
    Becket
    3 Bedrooms / 4 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Fireplace
    • Satellite TV
    • Air Conditioning
    • Stereo System
    • DVD Player
    • Internet Access
    • Deck
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Charming 3 bedroom home nestled on 5 acres of secluded woods in the beautiful Berkshire Mountains. Located in the lovely town of Becket on a private road. Completely updated home with a large, open floor plan. Master bedroom with attached private full bathroom on first floor, two additional... View all property information
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    Location Information
    Becket, Berkshires 01223
    From
    $233
    / Night
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    South Lee
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    traveller have booked this property
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    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Two Bedroom two bathroom condo located on beautiful resort in the Berkshires. Oak and Spruce Resort located 15 minutes to Tanglewood is the summer home in the Berkshires of the Boston Symphony Orchestra. Condominium sleeps 6 with an eat in kitchen and living area. Recreational activities, ample... View all property information
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    South Lee, Berkshires 01260
    From
    $266
    / Night
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    1 / 12
    Lee
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Grill
    • Refrigerator
    • Mountain Views
    • Satellite TV
    • Fireplace
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    cute cozy cottage, screened porch with views, close to everything, sleeps 4 . nice yard with big old trees and soft grass. gas bbq, just one mile to stockbridge center , Berkshire theatre festival. 5 miles to tanglewood, lenox , kripalu. 10 minutes to great barrington. bath has shower. full... View all property information
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    Location Information
    Lee, Berkshires 01238
    From
    $333
    / Night
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    1 / 10
    5 of 5 stars (2) Excellent
    Great Barrington
    2 Bedrooms / 1 Bathroom / Sleeps 5
    travellers have booked this property
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Internet Access
    • Mountain Views
    • DVD Player
    • Stereo System
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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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    $666
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    1 / 23
    5 of 5 stars (1) Excellent
    Stockbridge
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Water Views
    • Internet Access
    • Air Conditioning
    • Hot Tub
    • Mountain Views
    • Waterfront
    • Satellite TV
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    A home for the family: SKIING, SNOWSHOEING, AND SLEDDING. Fall and Winter availability. Behind the house, on the property is a HUGE hill that is great for sledding. 12 mins to Butternut. 25 mins to Jiminy. Across the road is a park that is great fun to hike, snowshoe, CC ski, and explore. A... View all property information
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    Location Information
    Stockbridge, Berkshires 01260
    From
    $619
    / Night
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    1 / 33
    5 of 5 stars (3) Excellent
    Great Barrington
    4 Bedrooms / 3 Bathrooms / Sleeps 12
    traveller have booked this property
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    Amenities & Details
    • Game Room
    • Stereo System
    • Boat Available
    • DVD Player
    • Mountain Views
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • 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
    $1,865
    / Week
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    1 / 13
    Hancock
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Mountain Views
    • Private Outdoor...
    • Satellite TV
    • Private Tennis Court
    • Sauna
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Luxury condo in hancock, ma ....Three bedrooms, loft, 2 baths, living room, kitchen with dining area, a/c, deck w/grill et al, heated pool, tennis court, mountain view. Near williamstown theater, clark art museum, tanglewood and three local golf courses. View all property information
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    Location Information
    Hancock, Berkshires 01237
    From
    $499
    / Night
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    1 / 5
    Lee
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Sauna
    • Air Conditioning
    • Hot Tub
    • Internet Access
    • Mountain Views
    • Shared Indoor Pool
    • Shared Tennis Court
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    I have a corner unit first floor 2-bed resort presidential suite in beautiful Berkshires! Just 2 hours drive down the Mass Pike from Boston. It's July 4th week and James Taylor will be playing at Tanglewood. This is one of the most sought after concerts every year and you wouldn't want to miss it!... View all property information
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    Location Information
    Lee, Berkshires 01238
    From
    $360
    / Night
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    1 / 4
    Hancock
    2 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Housekeeping...
    • Game Room
    • Shared Indoor Pool
    • Air Conditioning
    • Sauna
    • Wi-Fi
    • Ping Pong Table
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Exclusive Deal for Christmas week, the most wanted week of the year! Ski-In/Ski-Out Plus Year-Round Mountainside Fun! Wyndham Bentley Brook is situated right at the base of Jiminy Peak ski mountain, making this resort an exceptional choice for mountainside play. During the winter, ski out your... View all property information
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    Location Information
    Hancock, Berkshires 01237
    From
    $250
    / Night
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    1 / 12
    Great Barrington
    4 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Satellite TV
    • Private Fishing...
    • Watersports Nearby
    • Waterfront
    • Water Views
    • Mountain Views
    • Central Heating
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • 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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    Location Information
    Great Barrington, Berkshires 01236
    From
    $233
    / Night
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    1 / 12
    Windsor
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Enquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Peaceful, mountain hideaway. Rural, yet easily accessible to all major Berkshire County and Pioneer Valley attractions. Recently renovated, this charming 2-bedroom cottage can comfortably accommodate 4-6 people or could be a romantic retreat for two. Full kitchen with all appliances gives you... View all property information
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    Location Information
    Windsor, Berkshires 01270
    From
    $333
    / Night
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    Lenox
    2 Bedrooms / 1 Bathroom / Sleeps 5
    Overview Make Enquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This summer cottage built in the 1950's has recently been completely renovated from stem to stern to bring it up to date with the most current design standards. It is a 2-bedroom, 1-bathroom space with a beautiful backyard for grilling. There is also an amazing dining room surrounded by windows... View all property information
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    Location Information
    Lenox, Berkshires 01240