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Apartment Rentals and Condos in Pittsfield, MA and nearby

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    From
    $150
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    1 / 20
    5 of 5 stars (1) Excellent
    Pittsfield
    3 Bedrooms, 2 Bathrooms, Sleeps 8
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    $100
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    1 / 8
    4 of 5 stars (2) Very good
    Pittsfield
    1 Bedroom, 1 Bathroom, Sleeps 5
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    The following rentals are within 10 miles of Pittsfield, Massachusetts.

    From
    $249
    / Night
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    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 8
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    From
    $299
    / Night
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    Lee
    2 Bedrooms, 1 Bathroom, Sleeps 4
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    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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    Lee, Berkshires 01238
    From
    $350
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    1 / 22
    5 of 5 stars (11) Excellent
    Lee
    4 Bedrooms, 3 Bathrooms, Sleeps 8
    other travelers have booked this property
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    Overview Reviews (11)
    Amenities & Details
    • Wi-Fi
    • Washer
    • DVD Player
    • Mountain Views
    • Air Conditioning
    • Fireplace
    • TV
    • Ping Pong Table
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Enjoy all the Berkshires has to offer in our new (2014) restoration and outstanding renovation of the historic South Lee Schoolhouse. Perched on a hillside just across the road from the Housatonic River and Beartown State Forest in the hamlet of South Lee, just outside of Stockbridge, the 1892... View all property information
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    Lee, Berkshires 01260
    5 of 5 stars Reviewed September 3, 2015
    Mary has created the most beautiful family vacation home. The pictures are beautiful but don't do the home justice. It is lovely and immaculate. The home is stocked with...
    5 of 5 stars Reviewed August 28, 2015
    We loved the online description of the South Lee schoolhouse and were not disappointed. The house exceeded our expectations. The locations is superb, minutes from almost...
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    $500
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    Hinsdale
    4 Bedrooms, 3 Bathrooms, Sleeps 8
    other travelers 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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    Hinsdale, Berkshires 01235
    From
    $140
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    Hinsdale
    3 Bedrooms, 2 Bathrooms, Sleeps 7
    other travelers have booked this property
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    Overview
    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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    Hinsdale, Berkshires 01235
    From
    $200
    / Night
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    Cheshire
    2 Bedrooms, 1 Bathroom, Sleeps 5
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Waterfront
    • Air Conditioning
    • Ping Pong Table
    • Water Views
    • Satellite TV
    • Wi-Fi
    • Mountain Views
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Comfortable house situated on the shore of Hoosac Lake with beautiful, long views stretching across the large lake. It's fully furnished, with cable TV, stereo, and high-speed Internet. There's a big kitchen, with a central island for dining. The expansive living/dining room and attached study,... View all property information
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    Location Information
    Cheshire, Berkshires 01225
    From
    $175
    / Night
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    Windsor
    2 Bedrooms, 1 Bathroom, Sleeps 6
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    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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    Windsor, Berkshires 01270
    From
    $355
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    1 / 35
    4 of 5 stars (8) Very good
    Lee
    5 Bedrooms, 3 Bathrooms, Sleeps 11
    other travelers have booked this property
    Overview Reviews (8) Make Inquiry
    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 September 27, 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 September 3, 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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    From
    $300
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    1 / 25
    5 of 5 stars (2) Excellent
    Lee
    3 Bedrooms, 2 Bathrooms, Sleeps 5
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    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
    $400
    / Night
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    Lenox
    4 Bedrooms, 2 Bathrooms, Sleeps 10
    other traveler has booked this property
    Overview Make Inquiry
    Overview
    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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    Lenox, Berkshires 01240
    From
    $325
    / Night
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    1 / 10
    Richmond
    3 Bedrooms, 2 Bathrooms, Sleeps 8
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    In 1832, Josiah Loomis bought a parcel of land 'and the structures thereon', along what was then known as 'Massachusetts Turnpike No. 10,' the toll road between Albany, NY and Hartford, CT. Josiah Loomis, when he owned this property, could never have imagined what it would look like 180 years... View all property information
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    Richmond, Berkshires 01254
    From
    $750
    / Night
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    Lee
    5 Bedrooms, 5 Bathrooms, Sleeps 12
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    • 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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    $175
    / Night
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    1 / 2
    5 of 5 stars (1) Excellent
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 2
    Overview Reviews (1) Make Inquiry
    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 August 16, 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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    $250
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    Hancock
    2 Bedrooms, 1 Bathroom, Sleeps 6
    other traveler has booked this property
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    Amenities & Details
    • Dishwasher
    • Refrigerator
    • Linens Provided
    • Stove
    • TV
    • Central Heating
    • DVD Player
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Two Bedroom Ski Condo at base of Jiminy Peak. Renovated kitchen, fireplace, deck and a large livingroom with vaulted ceilings. Rent from the owner and save. View all property information
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    Location Information
    Hancock, Berkshires 01237
    From
    $150
    / Night
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    1 / 21
    5 of 5 stars (19) Excellent
    Lenox
    4 Bedrooms, 1 Bathroom, Sleeps 7
    other travelers have booked this property
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    Overview Reviews (19)
    Amenities & Details
    • Dryer
    • Stereo System
    • Grill
    • Internet Access
    • Central Heating
    • Washer
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Located on a quiet side street in the charming Berkshire town of Lenox, Gartner House is a great place to call home while exploring this scenic, historical, and culturally rich area of Western Massachusetts. Walk to breakfast, lunch or dinner at one of the town's many charming restaurants, explore... View all property information
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    Lenox, Berkshires 01240
    5 of 5 stars Reviewed January 3, 2015
    Ski trip in Berkshires and this place was perfect. Gave us nice options to do on off days. Debra was great with any issues that came up and was very helpful and responsive...
    5 of 5 stars Reviewed October 22, 2014
    We spent the weekend at the Gartner House in Lenox to visit my son at Shakespeare and Company. From my first contact with Deb, she was friendly and helpful. It is evident...
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    From
    $225
    / Night
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    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 8
    other travelers have booked this property
    Overview Make Inquiry
    Overview
    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
    From
    $450
    / Night
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    1 / 17
    5 of 5 stars (1) Excellent
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 2
    other traveler has booked this property
    Overview Reviews (1) Make Inquiry
    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 June 12, 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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    $250
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    1 / 12
    4 of 5 stars (1) Very good
    Lenox
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    other traveler has booked this property
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    Overview Reviews (1)
    Amenities & Details
    • Playground
    • Stereo System
    • Mountain Views
    • DVD Player
    • TV
    • Internet Access
    • Deck
    • Central Heating
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Charming, spacious and comfortable 1860's farmhouse adjacent to wildlife sanctuary. Cozy country decor with original wide plank floors, lovely views and outdoor dining or lounging on porch or deck. Walking distance to hiking trails in Pleasant Valley Wildlife Preserve or Kennedy Park. Quiet and... View all property information
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    Lenox, Berkshires 01240
    4 of 5 stars Reviewed July 8, 2015
    Lovely farmhouse, convenient to Tanglewood and shops in Lenox as well as other nearby towns and sights. We were a family of 7, including a 2 year old, and the swing set in the...
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    From
    $300
    / Night
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    New Lebanon, NY
    5 Bedrooms, 5 Bathrooms, Sleeps 5
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    This home sits on 10 private acres in the beautiful Berkshire mountains. Greeted by friendly wood carved bears, the entire estate consists of a 3 BR main house with 3.5 baths, two bedroom pool house with 1 bath, and 1 bedroom garage apartment with 1 bath. All units are available but this listings... View all property information
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    New Lebanon, New York 12125
    From
    $375
    / Night
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    Lee
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Overview
    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
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    $225
    / Night
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    1 / 14
    4.5 of 5 stars (3) Very good
    Hancock
    4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Amenities & Details
    • Central Heating
    • Stereo System
    • Mountain Views
    • Satellite TV
    • DVD Player
    • Playground
    • Internet Access
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Come and enjoy our beautiful mountain retreat - A home for every season. This charming home away from home is a wonderful place for family, friends and romance. Only 3 minutes from Jiminy Peak! With over 2200 square feet, this new country home has plenty of space for everyone yet a very cozy... View all property information
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    Location Information
    Hancock, Berkshires 001237
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    $150
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    1 / 11
    5 of 5 stars (4) Excellent
    Richmond
    3 Bedrooms, 1 Bathroom, Sleeps 6
    other travelers have booked this property
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    Overview Reviews (4)
    Amenities & Details
    • Air Conditioning
    • Water Views
    • Washer
    • Satellite TV
    • DVD Player
    • Internet Access
    • Playground
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Fantastic spot for families and for those looking for a quiet getaway. Come have some summer fun, enjoy the autumn colors or play in the snow. This year round cottage is the perfect spot for those who enjoy outdoor activities. The house is on a private dead end road, has a wonderful lake view... View all property information
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    Location Information
    Richmond, Berkshires 01254
    From
    $250
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    Lenox
    2 Bedrooms, 1 Bathroom, Sleeps 5
    Overview Make Inquiry
    Overview
    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
    From
    $450
    / Night
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    Richmond
    3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Overview
    Amenities & Details
    • Washer
    • Internet Access
    • Stereo System
    • Air Conditioning
    • Satellite TV
    • Shared Outdoor Pool...
    • Fireplace
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Newly furnished 3 bedroom (with AC) & 2 1/2 bath single family home with stunning deck and in ground pool nestled in the quiet countryside opposite a horse farm. Situated minutes from West Stockbridge convenience stores and restaurants. Property is on 2 quiet tree lined acres with an enclosed... View all property information
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    Richmond, Berkshires 01254
    From
    $300
    / Night
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    Washington
    4 Bedrooms, 2 Bathrooms, Sleeps 8
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Shingle style, timber frame, passive solar, Berkshie 'Cottage' Built along side of Coles Brook, the manor is a retreat destination any time of the year. The seclusion and tranquility of the custom built home and site are unique and comforting for family gatherings and weekend getaways. View all property information
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    Location Information
    Washington, Massachusetts 01223
    From
    $67
    / Night
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    Lee
    1 Bedroom, 1 Bathroom, Sleeps 1
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    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
    From
    $189
    / Night
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    1 / 16
    4 of 5 stars (1) Very good
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    other travelers have booked this property
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    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 October 25, 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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    5 of 5 stars (2) Excellent
    Hancock
    1 Bedroom, 1 Bathroom, Sleeps 6
    other travelers 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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    Hancock, Berkshires 01237
    5 of 5 stars Reviewed July 30, 2015
    This is a lovely rental in the heart of the Berkshires. Each morning you wake up to a view of Jiminy Peak and the sounds of bird life. Tom and Susan are wonderful innkeepers and...
    5 of 5 stars Reviewed October 16, 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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    $270
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    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 8
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    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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    Hancock, Berkshires 01237
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    5 of 5 stars (12) Excellent
    Lanesboro
    2 Bedrooms, 1 Bathroom, Sleeps 4
    other travelers have booked this property
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    Amenities & Details
    • Playground
    • Central Heating
    • Refrigerator
    • DVD Player
    • Stove
    • Grill
    • Internet Access
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    If you’ve driven by, you’ve wondered about the story of this beautiful stone building. Built in 1832 as a one-room schoolhouse – a function it served until 1950 -- this charming and historic building has been given new life as a vacation getaway. We are about 8 minutes away from Jiminy Peak and... View all property information
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    Lanesboro, Berkshires 01237
    5 of 5 stars Reviewed July 7, 2014
    We were lucky to happen upon this gem, and highly recommend it to families visiting the area of Mt. Greylock. Great on a rainy day, and interesting for all given the history of...
    5 of 5 stars Reviewed May 30, 2014
    We have stayed in several vacation rentals, and this one was extremely charming. The very first time I saw this one I just knew we had to vacation here while we were in The...
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    $229
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    1 / 4
    4 of 5 stars (1) Very good
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    other travelers have booked this property
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    Overview Reviews (1)
    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 August 11, 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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    $3,900
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    Hancock
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Inquiry
    Overview
    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 Beaver Pond, Hancock, Mass. Three bedrooms, loft, 2 baths, living room, kitchen with dining area, deck w/grill. Sledding on back terrace. Near Clark Art Museum, MassMoca. Williams College with schedule of sports open to the public: swimming, tennis, squash, basketball, skating and... View all property information
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    Hancock, Berkshires 01237
    From
    $200
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    1 / 8
    5 of 5 stars (1) Excellent
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 2
    other traveler has booked this property
    Overview Reviews (1) Make Inquiry
    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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    Lee, Berkshires 01238
    5 of 5 stars Reviewed June 17, 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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    $200
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    Lee
    1 Bedroom, 1 Bathroom, Sleeps 6
    other traveler 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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    Lee, Berkshires 01238
    From
    $155
    / Night
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    Lee
    1 Bedroom, 2 Bathrooms, Sleeps 5
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    Overview
    Amenities & Details
    • Wi-Fi
    • Mountain Views
    • Horse Riding Nearby
    • Patio
    • Grill
    • Watersports Nearby
    • Stove
    • 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
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    Lee, Berkshires 01238
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    $150
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    1 / 4
    5 of 5 stars (1) Excellent
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 2
    other traveler has booked this property
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    Overview Reviews (1)
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    first floor queensized bed, bath with shower. floors are wood ceiling has exposed beams and is furnished with oak antiques and a big wingbacked chair.built in bookshelf was from a companionway on a wooden sailing vessel owned by a sea captain that owned and ran the lodge back at the turn of the... View all property information
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    Lee, Berkshires 01238
    5 of 5 stars Reviewed June 17, 2014
    And I hope to stay here again in the future. I feel very comfortable here - good privacy, the house is huge, rustic charm, generally very quiet. The property is massive - and the...
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    $125
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    Lee
    1 Bedroom, 1 Bathroom, Sleeps 2
    other travelers have booked this property
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Linens Provided
    • Grill
    • Mountain Views
    • Parking
    • Balcony
    • Patio
    • Hot Tub
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    the garden room is a small room with a full sized bed. everything is floral, even the closet walls. it 's a sweet room with even a wood stove. it has an entrance to the courtyard just outside in the hall, the bath may be shared depending on the situation. bath has shower and lovely old sink. bath... View all property information
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    Lee, Berkshires 01238
    From
    $200
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    Lee
    1 Bedroom, 1 Bathroom, Sleeps 4
    Overview Make Inquiry
    Overview
    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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    Lee, Berkshires 01238
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    $250
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    1 / 11
    4 of 5 stars (2) Very good
    Lee
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Reviews (2) Make Inquiry
    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 June 18, 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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    1 / 18
    4.5 of 5 stars (9) Very good
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Amenities & Details
    • Skiing: Property Is...
    • Air Conditioning
    • Satellite TV
    • There Are Tennis...
    • Internet Access
    • Hot Tub
    • Sauna
    • Shared Indoor Pool
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Wyndham Bentley Brook Rental includes: King bed master, 2 doubles in the 2nd bedroom, queen sleep sofa, full living room, dining room and kitchen with utensils. New York + New Jersey Flock to Hancock Mass/Jiminy Peak Ski Area, rated Top 5 Family Mountains in the Northeast! Wyndham Bentley Brook... View all property information
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    Hancock, Berkshires 01237
    5 of 5 stars Reviewed March 23, 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 January 26, 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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    $300
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    1 / 25
    5 of 5 stars (8) Excellent
    Hancock
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Reviews (8) Make Inquiry
    Overview Reviews (8)
    Amenities & Details
    • Mountain Views
    • Stereo System
    • Central Heating
    • Deck
    • Satellite TV
    • DVD Player
    • Washer
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Secluded mountain home surrounded by 27 acres yet convenient to major attractions including Jiminy Peak, Williamstown, Hancock Shaker Village, Tanglewood, and MassMOCA. Home offers 3 bedrooms and 2 full baths with finished basement recreation room. Updated kitchen with all amenities needed for home... View all property information
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    Hancock, Berkshires 01237
    5 of 5 stars Reviewed July 7, 2015
    My eight year old daughter and I had a wonderful time staying in Hancock. We were joined at different times by young cousins and grandparents - the kids loved the inside (the bunk...
    5 of 5 stars Reviewed October 12, 2014
    Stayed here for a couple nights over labor day to get out of the city. The place is perfect for a group of 4 and even better for our 2 dogs. Great little creek for them to go...
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    $5,000
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    Lee
    5 Bedrooms, 6 Bathrooms, Sleeps 9
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Water Views
    • Watersports Nearby
    • Waterfront
    • Sauna
    • Wi-Fi
    • DVD Player
    • TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Custom designed Furnished Lake House in The Berkshires in Massachusetts on the Lee/Lenox line. Gorgeous western sunsets ! The home had 4/5 bedrooms and one is equipped as a nanny suite or teen haven. It is close to skiing, golf, outdoor sports, shopping, and all cultural venues. It is located... View all property information
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    Lee, Berkshires 01238