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Holiday Homes and Apartments Sandisfield, MA and nearby

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    $1,765
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    1 / 15
    5 of 5 stars (1) Excellent
    Sandisfield
    3 Bedrooms, 3 Bathrooms, Sleeps 6
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    The following rentals are within 25 kilometres of Sandisfield, Massachusetts.

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    $494
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    1 / 22
    5 of 5 stars (10) Excellent
    Lee
    4 Bedrooms, 3 Bathrooms, Sleeps 8
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    From
    $705
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    1 / 32
    5 of 5 stars (2) Excellent
    Stockbridge
    4 Bedrooms, 4 Bathrooms, Sleeps 12
    other travellers have booked this property
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    $282
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    1 / 11
    5 of 5 stars (15) Excellent
    Falls Village, CT
    2 Bedrooms, 1 Bathroom, Sleeps 4
    Overview Reviews (15) Make Enquiry
    Overview Reviews (15)
    Amenities & Details
    • Water Views
    • Deck
    • Stereo System
    • Satellite TV
    • Mountain Views
    • Central Heating
    • Hot Tub
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Rare property available for vacation rental in Falls Village Ct Originally dating to 1800 's this highly unique property was purchased in 1999 by artist and master craftsman Mario Genova. The interior features plaster throughout, stone, marble and terra cotta mosaic flooring and wonderful... View all property information
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    Location Information
    Falls Village, Connecticut 06031
    5 of 5 stars Reviewed 30 May 2015
    My husband and I stayed here for a recent visit on a trip to New England. We chose this Falls Village cottage and it was truly wonderful. Everything from the location, right up...
    5 of 5 stars Reviewed 10 April 2015
    I have been traveling to the northwest of Connecticut since my teens, spending a lot of weekends at Lime Rock and Sharon where my daughters spent their summers in a camp. There...
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    $388
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    1 / 32
    5 of 5 stars (2) Excellent
    Becket
    4 Bedrooms, 3 Bathrooms, Sleeps 8
    other travellers have booked this property
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    Overview Reviews (2)
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Come to the Berkshires and stay in one of the most beloved areas of Massachusetts. We are located close to Lenox, Stockbridge, Lee, Great Barrington and more. Our 3400 square foot ranch home is located in the heart of the Berkshires awaiting memorable times with your family and friends. Our... View all property information
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    Location Information
    Becket, Berkshires 01223
    5 of 5 stars Reviewed 19 August 2015
    Amazing place for its location, layout, and superb owner! 1. The location is ideal. It's under 3 miles to Jacobs Pillow Dance, about 25 minutes to Tanglewood, 12 minutes form...
    5 of 5 stars Reviewed 30 August 2014
    This was our first trip to the Berkshires and we feel fortunate to have found this fabulous home. It suited our needs perfectly as we were traveling with kids and grandparents...
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    $184
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    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Make Enquiry
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    Amenities & Details
    • Horse Riding Nearby
    • Washer
    • Central Heating
    • Dryer
    • Cooker
    • Housekeeping...
    • Wi-Fi
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Our 1762 Farmhouse is lovingly being restored with gardens in the Berkshires. Mission statement: Educating members in life, farming, and creative art skills acknowledging God as our provider. One mile from the Norman Rockwell Museum and 5 miles from Tanglewood. Come join the farm 'Agritourism'... View all property information
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    Location Information
    Stockbridge, Berkshires 01262
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    $239
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    1 / 50
    5 of 5 stars (6) Excellent
    North Egremont
    1 Bedroom, 1 Bathroom, Sleeps 2
    other travellers have booked this property
    Overview Reviews (6) Make Enquiry
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    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Mountain Views
    • Waterfront
    • Satellite TV
    • Water Views
    • Air Conditioning
    • Private Fishing...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    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,... View all property information
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    Location Information
    North Egremont, Berkshires 01230
    5 of 5 stars Reviewed 9 July 2015
    This suite is located in a beautiful serene setting. Barbara keeps the suite very clean, and her attention to every detail is unmatched. We had a wonderful stay, and only wish...
    5 of 5 stars Reviewed 12 September 2014
    I had a wonderful stay! The property is gorgeous and serene. The suite is clean, very nicely decorated and private. Absolutely lovely!
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    $212
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    1 / 16
    4.5 of 5 stars (3) Very good
    Stockbridge
    1 Bedroom, 1 Bathroom, Sleeps 4
    other travellers have booked this property
    Overview Reviews (3) Make Enquiry
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    Amenities & Details
    • TV
    • Refrigerator
    • Wi-Fi
    • Waterfront
    • Cooker
    • Linens Provided
    • Patio
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    One bedroom air conditioned apartment with private entrance in 18th century house in Historic District of Stockbridge. Wonderful views of the river, 18th green of Stockbridge Golf Club and the Berkshire Hills. 5 minutes walk to the famous Red Lion Inn/town center. Self contained and private. You... View all property information
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    Location Information
    Stockbridge, Berkshires 01262
    5 of 5 stars Reviewed 14 July 2015
    I just got back from my weekend stay here last night, and if I hadn't been so tired, I would have posted this review already! I was absolutely thrilled with this rental - where...
    4 of 5 stars Reviewed 21 June 2015
    Lovely home, great location, walking distance to the town of Stockbridge. Many things to see and do while we stayed for our five day trip. Must see: Naumkeg, Shrine of Divine...
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    $422
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    Lee
    2 Bedrooms, 1 Bathroom, Sleeps 4
    Overview Make Enquiry
    Overview
    Amenities & Details
    • There Are Tennis...
    • Air Conditioning
    • Watersports Nearby
    • Deck
    • TV
    • Washer
    • DVD Player
    • Boat Available
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Located in the tranquil hills of the beautiful Berkshires. This truly is a wooded wonderland filled with restful beauty and abundant wildlife. Wonderful retreat in the Berkshires. Private and secluded. Minutes from Tanglewood, The Red Lion Inn and The Norman Rockwell museum. Skiing. Private lake... View all property information
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    Location Information
    Lee, Berkshires 01238
    From
    $318
    / Night
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    Stockbridge
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Water Views
    • Fireplace
    • TV
    • Stereo System
    • Mountain Views
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This 1600 sq. ft. cottage boasts everything you would need for your visit to the Berkshires whether it be for a full summer / winter season to explore this beautiful area or a quick getaway to Tanglewood, The recently added master suite features a queen size bed, en-suite bathroom and a bonus... View all property information
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    Location Information
    Stockbridge, Berkshires 01262
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    $501
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    1 / 35
    4 of 5 stars (8) Very good
    Lee
    5 Bedrooms, 3 Bathrooms, Sleeps 11
    other travellers have booked this property
    Overview Reviews (8) Make Enquiry
    Overview Reviews (8)
    Amenities & Details
    • Mountain Views
    • Central Heating
    • Water Views
    • DVD Player
    • TV
    • Stereo System
    • Deck
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Beautiful house surrounded by protected woodland and a small beaver pond behind your backyard. All kinds of birds and wildlife. 5 Bedrooms, 2.5 baths, brand new kitchen, open living/dining room, laundry room. Wood stove that can function as a fireplace. 3 heating zones for comfort. All new... View all property information
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    Location Information
    Lee, Berkshires 01238
    4 of 5 stars Reviewed 28 September 2014
    We went there for a golf buddy trip and it was the perfect place for us in the Berkshires. Place was very clean, and had all the comforts of home. Robin is super friendly and...
    5 of 5 stars Reviewed 3 September 2014
    This is a wonderful home! Robin has taken care with the furnishing and finishings, which are a nice blend of antique and modern. Her love of the home and region is apparent...
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    $281
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    1 / 10
    5 of 5 stars (15) Excellent
    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 3
    other travellers have booked this property
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    Overview Reviews (15)
    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 18 August 2015
    We spent three nights at this lovely cottage, perfectly located a mere 7 minutes from town. The views from all windows are divine: mountains, rolling hills, endless big sky. We...
    5 of 5 stars Reviewed 9 August 2015
    This lovely spot was perfect for the two of us during our week in the Berkshires. Great Barrington is a beautiful town, well situated near great theater, music, dance...
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    $424
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    1 / 25
    5 of 5 stars (2) Excellent
    Lee
    3 Bedrooms, 2 Bathrooms, Sleeps 5
    Overview Reviews (2) Make Enquiry
    Overview Reviews (2)
    Amenities & Details
    • Fireplace
    • DVD Player
    • Satellite TV
    • Stereo System
    • Hot Tub
    • Internet Access
    • Deck
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    ** Rental is only available for 2 week minimum during the summer (July - August) Special Summer Deal -- Rent for the Season (July and August) and get either the last week in June OR the first week in September for half price! This adorable cottage has all the ingredients for the ultimate retreat... View all property information
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    Location Information
    Lee, Berkshires 01238
    From
    $281
    / Night
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    1 / 19
    4.5 of 5 stars (27) Very good
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (27) Make Enquiry
    Overview Reviews (27)
    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
    4 of 5 stars Reviewed 13 August 2015
      Want to feel like you have been invited to stay with an old - or new - friend in a special part of the Berkshires, then this is the place for you. Only 4 mi...
    3 of 5 stars Reviewed 10 August 2015
    Beautiful location with lovely outdoor space! Antique Suite has spacious rooms and a very comfortable bed. Hostess made every effort to see that we enjoyed our stay, inquiring...
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    From
    $353
    / Night
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    Great Barrington
    5 Bedrooms, 6 Bathrooms, Sleeps 8
    Overview Make Enquiry
    Overview
    Amenities & Details
    • DVD Player
    • Waterfront
    • Satellite TV
    • Deck
    • Stereo System
    • Wi-Fi
    • Fireplace
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Welcome to my dream come true! Pick from your own orchards, vegetable gardens and perennial beds. Swim in your own Green River or your beautiful heated swimming pool. And of course, SKI, SKI, SKI!! This home is beautiful four seasons of the year. Major highlights include a fireplace in the kitchen... View all property information
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    Location Information
    Great Barrington, Berkshires 01230
    From
    $494
    / Night
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    1 / 27
    3.5 of 5 stars (2) Average
    Great Barrington
    5 Bedrooms, 4 Bathrooms, Sleeps 10
    other travellers have booked this property
    Overview Reviews (2) Make Enquiry
    Overview Reviews (2)
    Amenities & Details
    • Deck
    • Stereo System
    • Air Conditioning
    • Satellite TV
    • Mountain Views
    • DVD Player
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Shaker Hill is a quirky rambling farmhouse located less than 3 hours from NYC and Boston. Hidden away down a 400’ unpaved driveway on 30 acres of fields and forest in the heart of the Berkshires, Shaker Hill is totally private and surrounded by 30 acres of rolling fields, diverse wetlands,... View all property information
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    Location Information
    Great Barrington, Berkshires 01230
    3 of 5 stars Reviewed 12 September 2014
    This is a very large house, more than adequate in size for a group of ten people. It has a big yard and a spectacular view of the mountains, especially from an upstairs window...
    4 of 5 stars Reviewed 5 January 2015
    MAにあるSki Butternut というスキー場を利用するため、クリスマスからお正月にかけて、6泊7日で滞在しました。4家族(大人7人、子供5人・子供は5歳と7歳)というグループでしたが部屋の広さは十分で、非常に快適に過ごすことができました。 【ロケーション】 Butternut...
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    From
    $706
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    Tyringham
    4 Bedrooms, 2 Bathrooms, Sleeps 8
    other traveller has booked this property
    Overview Make Enquiry
    Overview
    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
    From
    $353
    / Night
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    Tyringham
    1 Bedroom, 1 Bathroom, Sleeps 4
    Overview Make Enquiry
    Overview
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Santarella Estate and Gardens in Tyringham, MA is a magical destination in the heart of one of the Berkshires' most beautiful valleys, located 3 miles from Interstate 90 and 15 minutes from most of the principal attractions (Tanglewood, Jacob's Pillow, Norman Rockwell museum, etc.) Pictures are... View all property information
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    Location Information
    Tyringham, Berkshires 01264
    From
    $388
    / Night
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    Monterey
    5 Bedrooms, 3 Bathrooms, Sleeps 12
    other traveller has booked this property
    Overview Make Enquiry
    Overview
    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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    $530
    / Night
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    1 / 10
    5 of 5 stars (2) Excellent
    Sheffield
    3 Bedrooms, 6 Bathrooms, Sleeps 8
    Overview Reviews (2) Make Enquiry
    Overview Reviews (2)
    Amenities & Details
    • Air Conditioning
    • Watersports Nearby
    • Housekeeping...
    • Hot Tub
    • TV
    • There Are Tennis...
    • Mountain Views
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Charmingly restored 1840 cottage in the apple orchard of a working organic farm. Completely renovated in 2015 with thoughtful amenities, fresh eggs and produce and acres of trails and views. Close to waterfalls and lakes. Nearby ski hills, Tanglewood concerts, theatre, film festival, dance and... View all property information
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    Location Information
    Sheffield, Berkshires 01257
    5 of 5 stars Reviewed 25 July 2015
    New England working farm. Lovely setting Great hospitality. Easy access to Tanglewood and other Berkshire attractions.
    5 of 5 stars Reviewed 23 July 2015
    What a beautifully decorated and comfortable cottage! Incredible deck for long lazy summer afternoons. Property owners were wonderful ... friendly & helpful. Cannot wait to...
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    From
    $95
    / Night
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    Lee
    1 Bedroom, 1 Bathroom, Sleeps 1
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Patio
    • Wi-Fi
    • Refrigerator
    • There Are Tennis...
    • Satellite TV
    • Central Heating
    • Dryer
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Share a beautifully renovated Victorian home, in downtown Lee, Ma, right in the heart of the Berkshires. Walking distance to town, and on the bus line. Wifi, cable TV, off street parking. Shared kitchen and bath. I have two cats and one other housemate. I am a gospel and blues musician. This is a... View all property information
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    Location Information
    Lee, Berkshires 01238
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    $177
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    1 / 12
    5 of 5 stars (3) Excellent
    Alford
    1 Bedroom, 1 Bathroom, Sleeps 2
    other travellers have booked this property
    Overview Reviews (3) Make Enquiry
    Overview Reviews (3)
    Amenities & Details
    • Hot Tub
    • Mountain Views
    • Satellite TV
    • Waterfront
    • Water Views
    • Wi-Fi
    • Air Conditioning
    • Housekeeping...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    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... View all property information
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    Location Information
    Alford, Massachusetts 01266
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    $318
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    1 / 16
    5 of 5 stars (5) Excellent
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 7
    other travellers have booked this property
    Overview Reviews (5) Make Enquiry
    Overview Reviews (5)
    Amenities & Details
    • Boat Available
    • There Are Tennis...
    • Watersports Nearby
    • Fireplace
    • Satellite TV
    • Washer
    • Internet Access
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located a short walk to the town beach on the Stockbridge Bowl, and 1.5 miles from Tanglewood's Hawthorn entrance, this casual summer cottage is a great get away for the whole family. The master bedroom is equipped with a queen bed; two twins in the 2nd bedroom, and a full-size bed in the 3rd... View all property information
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    Location Information
    Stockbridge, Berkshires 01262
    5 of 5 stars Reviewed 1 August 2015
    This was a wonderful place to spend a family vacation. The house is immaculate, functional and well furnished. The proximity to all of the many venues and activities the area...
    4 of 5 stars Reviewed 24 October 2013
    Some friends and I wanted to have a reunion as we are spread out along the east coast, and we were debating between camping or renting. I heard no end of the gratitude from my...
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    From
    $953
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    Great Barrington
    4 Bedrooms, 6 Bathrooms, Sleeps 12
    Overview Make Enquiry
    Overview
    Amenities & Details
    • TV
    • Washer
    • Dryer
    • Internet Access
    • Air Conditioning
    • Fireplace
    • Grill
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This immaculate home is the place for relaxing, entertaining and sharing great times with family and friends. The house sets over 4 beautifully wooded acres. We call it the 'illision of seclusion,' as it is very private and yet is 5 minutes from the town as well as lakes, hiking, movies, theater,... View all property information
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    Location Information
    Great Barrington, Berkshires 01236
    From
    $2,260
    / Week
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    New Marlborough
    4 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Grill
    • Dryer
    • Central Heating
    • Wi-Fi
    • Washer
    • DVD Player
    • Refrigerator
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Welcome to Mill River, and our 1905 Queen Anne style Victorian backing onto hundreds of acres of woods, deep in the heart of the Berkshires. Step in and enjoy the peace of sitting on the porch of an old house on a quiet country lane, the wind in the trees and the babble of the nearby stream. The... View all property information
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    Location Information
    New Marlborough, Berkshires 01230
    From
    $1,059
    / Night
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    Lee
    5 Bedrooms, 5 Bathrooms, Sleeps 12
    Overview Make Enquiry
    Overview
    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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    $424
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    1 / 9
    1 of 5 stars (1) Terrible
    Housatonic
    4 Bedrooms, 3 Bathrooms, Sleeps 10
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    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
    1 of 5 stars Reviewed 15 August 2015
    After our initial rental fell through due to water damage at the last minute before we left Florida for the Berkshires, we found this rental and took it. We have a dog and there...
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    $3,460
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    Great Barrington
    5 Bedrooms, 3 Bathrooms, Sleeps 10
    other traveller has booked this property
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    Overview
    Amenities & Details
    • Mountain Views
    • Deck
    • Satellite TV
    • Waterfront
    • Internet Access
    • DVD Player
    • Water Views
    • Boat Available
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Attractive year-round lakefront house in a wooded area on a pristine Round Pond in the Berkshires. Relax and enjoy the view from your deck or dock. Fish from the dock or take the boat out onto the lake. Ideal family retreat in Great Barrington and only a short drive to cultural attractions... View all property information
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    Location Information
    Great Barrington, Berkshires 01236
    From
    $282
    / Night
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    Great Barrington
    2 Bedrooms, 1 Bathroom, Sleeps 4
    other travellers have booked this property
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    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
    $635
    / Night
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    1 / 17
    5 of 5 stars (1) Excellent
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 2
    other traveller has booked this property
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Amenities & Details
    • Central Heating
    • Fireplace
    • Internet Access
    • Washer
    • Mountain Views
    • Hot Tub
    • Dryer
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    handsome and welcoming, this authentic Berkshire lodge will make you feel like you`re in an old fashioned Christmas card! fireplace blazing, wood floors post and beam, hand planed planks. in the kitchen the floor is marble slabs from the famous lee marble quarry. Daniel Chester French, the designer... View all property information
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    Location Information
    Lee, Berkshires 01238
    5 of 5 stars Reviewed 13 June 2014
    I had several summer months here, it never disappoints. Full of nature's bounty, hospitable host, friendly vacationers. Very close to all the best of the Berkshires, Tanglewood...
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    $494
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    1 / 11
    5 of 5 stars (1) Excellent
    Great Barrington
    4 Bedrooms, 2 Bathrooms, Sleeps 9
    other travellers have booked this property
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    Overview Reviews (1)
    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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    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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    $353
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    1 / 13
    5 of 5 stars (2) Excellent
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (2) Make Enquiry
    Overview Reviews (2)
    Amenities & Details
    • Stereo System
    • Washer
    • Air Conditioning
    • Satellite TV
    • Fireplace
    • DVD Player
    • Internet Access
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Welcome to our family getaway in the Berkshires which we also rent out. Set on 2 acres in the Stockbridge hamlet of Glendale, the house is conveniently located - just a short walk to the Norman Rockwell Museum, Chesterwood House, and Botanical Gardens. The sunny 1st floor features a living room... View all property information
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    Location Information
    Stockbridge, Berkshires 01262
    5 of 5 stars Reviewed 27 May 2015
    This home is beautiful! It is an older home, and comes with the charm and quirks, which make it even more lovely! The décor is modern, simple and fits the house wonderfully. The...
    5 of 5 stars Reviewed 23 January 2015
    This home has everything. It also happens to be a wonderfully furnished home. The home owner left little treats for us as we arrived late the first night. The surrounding...
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    $318
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    1 / 11
    3.5 of 5 stars (3) Average
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    other travellers have booked this property
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    Overview Reviews (3)
    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
    4 of 5 stars Reviewed 15 July 2015
    Those who used the cottage this week ranged from me alone to one night with eight people for one night. Sleeping was not a problem. The house is ideally located between Lenox...
    3 of 5 stars Reviewed 4 July 2015
    On the water with canoes, close to Tanglewood, but tired amenities. Poor second bedroom, not yet cleaned until after we arrived, but most unfortunate it was a very hot weekend...
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    $6,355
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    Great Barrington
    6 Bedrooms, 6 Bathrooms, Sleeps 12
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Playground
    • Internet Access
    • Mountain Views
    • Fireplace
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This home is uniquely and magnificently furnished by a retired couple that spent 18 years traveling and living abroad. Even local real estate agents have called the house “special”. It has 7,000 sf of living space (3 floors) with plenty of places to be together or to be alone (as one so chooses).... View all property information
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    Location Information
    Great Barrington, Berkshires 01230
    From
    $366
    / Night
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    Tyringham
    3 Bedrooms, 3 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • DVD Player
    • Deck
    • Dryer
    • Washer
    • Mountain Views
    • Central Heating
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This turn of the century cottage is located on a 130 acre property, and is stocked with linens. Three and a half baths, three full bedrooms, kitchen, living room, dining room, screened porches, a deck, and washer dryer. The house is across the brook and up a stone staircase (30 steps) from the... View all property information
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    Location Information
    Tyringham, Berkshires 01264
    From
    $282
    / Night
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    1 / 8
    5 of 5 stars (1) Excellent
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 2
    other traveller has booked this property
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Amenities & Details
    • Hot Tub
    • Garage
    • Mountain Views
    • Internet Access
    • Air Conditioning
    • Fireplace
    • Stereo System
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    The Writer's Room is at the top of the stairs on the right. This handsome room is made completely of wood. Ceilings are higher and there's a sitting area in the big dormer. dormer faces east and get the morning sun! The floors are wide plank cherry milled from the property. the walls are pine.... View all property information
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    Location Information
    Lee, Berkshires 01238
    5 of 5 stars Reviewed 18 June 2014
    We have taken the Writer's Room each Summer for about three years now. We find the Lodge to be authentic New England... our natural wood room to the rest of the house. It is...
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    $353
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    1 / 11
    4 of 5 stars (2) Very good
    Lee
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Reviews (2) Make Enquiry
    Overview Reviews (2)
    Amenities & Details
    • Mountain Views
    • Internet Access
    • Dryer
    • Satellite TV
    • Washer
    • DVD Player
    • Stereo System
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Experience a little of old New England. Our vacation rental is a charming historic family farmhouse apartment with lots of room and comfort,2100Sq.ft., situated on 22 acres. Built in 1782, our farm was famous for breeding Plymouth Barred Rock chickens. In the 1800's, one of these barred rock... View all property information
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    Lee, Berkshires 01238
    4 of 5 stars Reviewed 18 June 2013
    This property was a great home base for our brief visit to the Berkshires. Plenty of space and well equipped. We especially enjoyed the beautiful property, whether sitting on the...
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    $741
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    1 / 35
    5 of 5 stars (16) Excellent
    Sheffield
    4 Bedrooms, 3 Bathrooms, Sleeps 8
    Overview Reviews (16) Make Enquiry
    Overview Reviews (16)
    Amenities & Details
    • Satellite TV
    • Internet Access
    • Deck
    • DVD Player
    • Stereo System
    • Mountain Views
    • Hot Tub
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Enjoy your vacation in a beautiful historic house located in the heart of the Berkshires. Located two and a quarter hours north of New York City, this circa-1770s center chimney colonial will charm and delight your family and guests. 88 acres of land with views of Mt. Washington and Mount Everett... View all property information
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    Location Information
    Sheffield, Berkshires 01257
    From
    $265
    / Night
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    1 / 12
    Great Barrington
    4 Bedrooms, 2 Bathrooms, Sleeps 10
    Overview Make Enquiry
    Overview
    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
    $282
    / Night
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    Lee
    1 Bedroom, 1 Bathroom, Sleeps 6
    other traveller has booked this property
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    Overview
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    sleeps 4 can combine with writer's room for large suite, private entrance. fireplace or windowed woodstove, ceiling fans cathedral ceiling, terrace with seating, pasture and forest views. windows line both sides of room and feels like a treehouse. beautiful wood floors and soft carpets make you... View all property information
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    Location Information
    Lee, Berkshires 01238
    From
    $1,200
    / Week
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    Becket
    2 Bedrooms, 1 Bathroom, Sleeps 4
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Waterfront
    • Wi-Fi
    • Stereo System
    • Private Fishing...
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Lovely house on pond, Beautiful views of pond from every room, except one. Lounge on the deck with a glass of wine watch the Great Blue Heron has he stalks his fish, see the beavers swim lazily across the pond, flapping their tails to let you know they are there. Every room but one has a water... View all property information
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    Location Information
    Becket, Berkshires 01223
    From
    $247
    / Night
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    1 / 13
    4.5 of 5 stars (14) Very good
    Monterey
    3 Bedrooms, 2 Bathrooms, Sleeps 7
    other traveller has booked this property
    Overview Reviews (14) Make Enquiry
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    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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    Monterey, Berkshires 01245 0933
    4 of 5 stars Reviewed 20 July 2015
    What a relaxing, quiet getaway! The cabin was rustic, roomy and secluded. Fully stocked with just about everything you could possibly need to enjoy your stay. We saw two bears...
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    $196
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    1 / 16
    5 of 5 stars (9) Excellent
    Becket
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    other travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Boat Available
    • Waterfront
    • Stereo System
    • Satellite TV
    • Water Views
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Pretty cottage in the woods on a beautiful private lake with a stream running through the property's two acres of land. Newly constructed, spacious and sunny second floor with views of the lake. Hardwood floors throughout the house. Swim, kayak, canoe or fish from the back yard, or just lounge... View all property information
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    Becket, Berkshires 01223
    5 of 5 stars Reviewed 18 January 2014
    We had a wonderful time in the Berkshires, and this cottage was the central part of our weekend. The house was superb and extra clean, with everything provided. Views were...
    5 of 5 stars Reviewed 2 October 2013
    Excellent spot for a quiet retreat. Located on a nice pond with just a few neighbors we never even saw or heard. The cottage has all the essentials. Very clean and inviting...
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    $154
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    1 / 13
    5 of 5 stars (8) Excellent
    Becket
    2 Bedrooms, 1 Bathroom, Sleeps 4
    other travellers have booked this property
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    Amenities & Details
    • Satellite TV
    • Dryer
    • Deck
    • Washer
    • Stereo System
    • Air Conditioning
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Remember the simple pleasures of a country, lakeside vacation where you can spend the day swimming or boating, exploring new towns and attractions, or just spending a lazy afternoon reading on the screened-in porch? Get back to those simple pleasures in our cabin, which is located in a beautiful,... View all property information
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    Becket, Berkshires 01223
    5 of 5 stars Reviewed 4 November 2014
    This was exactly what we were looking for in a getaway rental! The place was exactly as described and every bit of the transaction went by without a hitch. The house was cozy...
    5 of 5 stars Reviewed 29 June 2014
    The Becket cabin is a great getaway for young families. Our 4- and 2-year-old happily played about in and around the cabin and we spent a lot of time building fires in the fire...
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    $247
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    1 / 2
    5 of 5 stars (1) Excellent
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 2
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Sunny, light , bright and wide! the queens room is one of the biggest rooms and has private ensuite bathroom with tub/shower. 2 big closets, large writing desk, comfy conversation area, 2 dressers full sized bed. a section of the room has original ceilings so persons taller than 6'2' would be... View all property information
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    Lee, Berkshires 01238
    5 of 5 stars Reviewed 17 August 2015
    I had the pleasure of staying at the Chestnut Lodge in the Queen's room. From the moment you step into the foyer you are taken back to a simpler time in this historic lodge. The...
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    $353
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    Great Barrington
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    other traveller has booked this property
    Overview Make Enquiry
    Overview
    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
    $706
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    1 / 20
    5 of 5 stars (8) Excellent
    Sheffield
    4 Bedrooms, 3 Bathrooms, Sleeps 15
    Overview Reviews (8) Make Enquiry
    Overview Reviews (8)
    Amenities & Details
    • Deck
    • Hot Tub
    • Shared Outdoor Pool...
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    The Race Mountain House is set high on the slopes of the Taconic Mountains in Southern Berkshire County. Large, east-facing windows look out over a sweeping view of the Housatonic River Valley. In the early hours, the house floods with warm morning light and sunrises are spectacular. The inviting,... View all property information
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    Location Information
    Sheffield, Berkshires 01257
    5 of 5 stars Reviewed 7 August 2014
    Casey's place was really lovely - just exactly as described! WONDERFUL central great room/dining room for our large group to gather and relax - and beautiful decks for reading...
    5 of 5 stars Reviewed 24 February 2014
    Racebrook Lodge is our "home away from home", and Casey and Dave (the owners) are so incredibly hospitable. This house, their most recent addition to the property, is the GEM of...
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    $353
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    5 of 5 stars (2) Excellent
    Great Barrington
    2 Bedrooms, 1 Bathroom, Sleeps 5
    other travellers have booked this property
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    Overview Reviews (2)
    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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    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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    $424
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    1 / 16
    Becket
    3 Bedrooms, 4 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    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
    $219
    / Night
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    Lee
    1 Bedroom, 2 Bathrooms, Sleeps 5
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Wi-Fi
    • Mountain Views
    • Horse Riding Nearby
    • Patio
    • Grill
    • Watersports Nearby
    • Cooker
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    This is the second floor of the barn. Open cathedral ceiling. Wooden interior with open floor plan. Big queen sized bed with canopy . 2 twin beds. Great for traveling with family or friends. Kitchen area has microwave, mini fridge, induction cooktop, hot pot and coffeemaker. Bathroom has... View all property information
    Make Enquiry
    Location Information
    Lee, Berkshires 01238