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Cabin Rentals and Cabins in Berkshires, MA

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    1 / 18
    5 of 5 stars (11) Excellent
    Becket
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 13
    5 of 5 stars (8) Excellent
    Becket
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 16
    5 of 5 stars (1) Excellent
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 4
    5 of 5 stars (1) Excellent
    Lee
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    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
    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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    1 / 2
    5 of 5 stars (1) Excellent
    Lee
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    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
    Location Information
    Lee, Berkshires
    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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    1 / 20
    5 of 5 stars (6) Excellent
    West Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Mountain Views
    • Wi-Fi
    • Balcony
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    • Central Heating
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    • x
    About this property
    Located in West Stockbridge minutes from everything . Nestled in the Berkshire Mountains. Convenient yet Private. Visit our web-site aberkshirehome. The Berkshires is a world unto itself. It is scenic beauty married to cultural bounty. It is urban sophistication in an idyllic, rural setting. It is... View all property information
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    West Stockbridge, Berkshires
    5 of 5 stars Reviewed 4 weeks ago
    We had a wonderful stay in this large, lovely house that contained everything we needed for comfort and convenience. We were impressed with the degree to which details were...
    5 of 5 stars Reviewed November 2, 2014
    Had an outstanding couple of weeks staying here; place was quiet, peaceful and not too far from civilization. All the amenities and space you could wish for and Cassandra and her...
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    1 / 21
    Monterey
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Skiing: Property Is...
    • Patio
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    • 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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    Monterey, Berkshires
    1 / 16
    5 of 5 stars (5) Excellent
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Satellite TV
    • Porch
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    • x
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    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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    Stockbridge, Berkshires
    5 of 5 stars Reviewed July 31, 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 October 24, 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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    1 / 8
    5 of 5 stars (1) Excellent
    Lee
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Hot Tub
    • Outdoor Dining Area
    • Mountain Views
    • Internet Access
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    • Balcony
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    • 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
    Location Information
    Lee, Berkshires
    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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    1 / 10
    West Stockbridge
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Washer
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    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Rent a comfortable 1840 farmhouse with 26 acres in the Berkshire mountains. Walk to the village of West Stockbridge or a short drive to all the Berkshire attractions. Close to the ski resorts of Butternut, Bousquet, Catamount and Jiminy Peak. The house sleeps 10 to 12 people and is fully equipped.... View all property information
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    West Stockbridge, Berkshires
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    1 / 6
    Lee
    1 Bedroom, 3 Bathrooms, Sleeps 5 | Quick View
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    • Grill
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    • Shared Yard
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    • x
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    • 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
    1 / 12
    4 of 5 stars (1) Very good
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Porch
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    • Mountain Views
    • Satellite TV
    • Grill
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    cute cozy cottage, screened porch with views, close to everything, sleeps 2 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
    4 of 5 stars Reviewed August 12, 2016
    We stayed at Jo-Anne's cottage for a week in mid-July. Wasn't sure what to expect as the place had no reviews. Our hostess made us feel at home right away and made a major...
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    1 / 10
    4.5 of 5 stars (15) Very good
    Lanesboro
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Grill
    • Outdoor Dining Area
    • Central Heating
    • Mountain Views
    • Internet Access
    • DVD Player
    • Shared Yard
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    4 of 5 stars Reviewed August 3, 2016
    Private and peaceful. Located where many cultural activities are available.Caring hosts.Our 2nd year!
    5 of 5 stars Reviewed February 12, 2016
    My boyfriend and I celebrated my birthday weekend at the cottage. We had a rough start the day we were to arrive and Cheryl was just wonderful and so understanding. We were...
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    1 / 10
    Lee
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • ?
    • ?
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    • 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
    1 / 4
    4 of 5 stars (1) Very good
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Satellite TV
    • Mountain Views
    • Internet Access
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    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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    1 / 8
    5 of 5 stars (2) Excellent
    West Stockbridge
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Internet Access
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    • Pet-friendly
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    • ?
    • ?
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    • ?
    About this property
    Cozy and modern two bedroom and one bath vacation home with lake nearby Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This luxury home can sleep up to 6 people and has lake access nearby. Enjoy a nice cup of hot chocolate by the fireplace in the living... View all property information
    Location Information
    West Stockbridge, Berkshires
    5 of 5 stars Reviewed December 18, 2013
    We stayed at this home in Housatonic, which is part of Great Barrington, the Smithsonian pic for best small town in the USA. I hope you all don't however as one of the best...
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    1 / 26
    Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Newly renovated contemporary house on 2 acres in Stockbridge. Great space surrounding house for outdoor sports and sitting around the fire at night. 3 bedrooms, 3 bathrooms, indoor fireplace, wood floors, many windows and closets. Large kitchen. WiFi. Master bedroom has king bed and master... View all property information
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    Stockbridge, Berkshires
    1 / 10
    South Egremont
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
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    • x
    About this property
    complete home 3 bedrooms,2 baths,living,dining,kitchen,and large deck(with a great view).Great location,at the foot of Mt.Washington state forest,next door to Jug End preserve,near Bash Bish falls.2 miles to Catamount ski area,5 to Gt.Barrington MA,5 to Hillsdale NY,10 to Twin Lakes,and salisbury... View all property information
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    South Egremont, Berkshires
    1 / 32
    5 of 5 stars (4) Excellent
    Becket
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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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    Becket, Berkshires
    5 of 5 stars Reviewed August 21, 2016
    My family and friends - group of 8 just spent an amazing week at this home. The house was a perfect size, clean and fully stocked. We made gourmet breakfasts, lunches & dinners...
    5 of 5 stars Reviewed May 14, 2016
    The Levy's home was perfect for our intergenerational family, including a 7month old grandaughter. We were pleasantly surprised by how well the home was supplied and organized...
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    1 / 52
    5 of 5 stars (8) Excellent
    North Egremont
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Wi-Fi
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    • Waterfront
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    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
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    • ?
    About this property
    Located in the Berkshire mountains on more than 5 acres <BR>surrounded by 29 acres of conservation land. Featuring<BR>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,... View all property information
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    North Egremont, Berkshires
    5 of 5 stars Reviewed July 19, 2016
    From the moment we turned off the beautiful country road and into River Song's driveway my wife and I sensed we were in for a treat. Barbara and Phillip came out to meet us and...
    5 of 5 stars Reviewed October 7, 2015
    My husband and I were looking for a relaxing getaway for a long weekend. We chose the River Song and were not disappointed. The suite is beautifully and comfortably furnished...
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    1 / 26
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Shared Outdoor Pool...
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    • x
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    • x
    About this property
    Let this quaint 2-bedroom, 2-bathroom Hancock condo, which sleeps 6, be the perfect destination for your New England escape! This excellent property carries an abundance of amenities to make your northeast vacation one you’ll always cherish. Nestled along the scenic border of New York and... View all property information
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    Hancock, Berkshires
    1 / 16
    4.5 of 5 stars (2) Very good
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Central Heating
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    • Shared Indoor Pool
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    • Sauna
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    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • x
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    • 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
    5 of 5 stars Reviewed September 5, 2015
    Great location near all outdoor activities including hiking, biking, golf and water sports. Rooms were spacious with 3 TVs. Wi-Fi was fast. One of the poops was heated. Owner...
    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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    1 / 11
    3.5 of 5 stars (4) Average
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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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    Stockbridge, Berkshires
    4 of 5 stars Reviewed July 21, 2016
    The Stockbridge House was exactly what we expected from the description and pictures. The home is rustic and cozy, like a cabin in the woods. Having water access to the bowl was...
    4 of 5 stars Reviewed July 14, 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...
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    1 / 6
    5 of 5 stars (3) Excellent
    Savoy
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    Located in a quiet corner of the northern Berkshires, this lovely two-bedroom home has a combined living room/kitchen with cathedral ceilings and a spacious bathroom complete with a 2-person jacuzzi tub. The house is located about a mile from beautiful Tannery Falls in the Savoy State Forest and... View all property information
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    Savoy, Berkshires
    5 of 5 stars Reviewed February 3, 2016
    What a quaint and absolutely lovely place to have spent the weekend. The quiet and peaceful surroundings along with the gorgeous wood interior made for a very homey and...
    5 of 5 stars Reviewed December 9, 2015
    Words can't begin to describe how amazing this rental is! My husband and I were married in November of 2014. Being a teacher, we couldn't go away for a long honeymoon so we...
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    1 / 32
    5 of 5 stars (2) Excellent
    Stockbridge
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    We call this house ‘South Sedgwick’ because of its location on a piece of land formerly used by the Sedgwick family for picnicking–an ideal spot for relaxation with stunning views of Monument Mountain and Ice Glen. The house is newly constructed with ash hardwood floors, custom white pine trim and... View all property information
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    Stockbridge, Berkshires
    5 of 5 stars Reviewed December 3, 2014
    What a great place! Teva was wonderful to work with, communication was incredible, and he is very welcoming. The house was spacious, very comfortable with 9 people! Teva came by...
    5 of 5 stars Reviewed July 18, 2014
    Our family of 5 rented this home over July 4th weekend and we couldn't have been more pleased. The home has just been newly renovated, is very tastefully appointed and looks and...
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    1 / 20
    5 of 5 stars (25) Excellent
    West Stockbridge
    5 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • Central Heating
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    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Quaint, , 2 story 1850's farmhouse in the Berkshires with original ceiling beams and 16" floor boards in much of the house. Fully furnished with 5 bedrooms, 2 full baths and a gorgeous screened-in porch overlooking 4 acres of gardens, stream and wooded mountains. Country kitchen with dish washer,... View all property information
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    West Stockbridge, Berkshires
    5 of 5 stars Reviewed May 9, 2016
    Our group of eight adults had a very wonderful experience at Elaine's Berkshire farmhouse. We found it in excellent condition. Full kitchen had everything we needed to create...
    5 of 5 stars Reviewed March 30, 2016
    Some girlfriends and I decided to meet up for a weekend and found this wonderful home which was super convenient for all of us - some coming from MA others from upstate NY. When...
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    1 / 14
    5 of 5 stars (2) Excellent
    Lee
    6 Bedrooms, 5 Bathrooms, Sleeps 26 | Quick View
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    • x
    About this property
    220 acres with tennis, indoor & outdoor pools, yoga studio, gym and lakefront. Built by Westinghouse and then part of the Vanderbilt Estate, The Playhouse is a newly renovated iconic Berkshire's property that once served as a theater space for America's greatest innovators, and is now hung with... View all property information
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    Lee, Berkshires
    5 of 5 stars Reviewed August 11, 2016
    The Playhouse is a magical place to connect with friends and family. There are a half dozen living spaces that offer anything from quiet reading areas with a view, to 40 person...
    5 of 5 stars Reviewed August 11, 2016
    I didn't want to leave. The view from the picture window is breathtaking. The home has more space than even our large group could fill. If you are a yogi, you can enjoy your own...
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    1 / 22
    Otis
    6 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    • x
    About this property
    THIS IS A FULLY FURNISHED LARGE RETREAT IN THE HEART OF THE BERKSHIRES...SKIIING, LAKES, ANTIQUES, CRAFT SHOWS, ARTS, THEATRE ALL NEAR BY.....HOME IS IN A PRIVATE COMMUNITY WITH ITS OWN LAKE, POOLS, STATE OF THE ART FITNESS CENTER, CLUBHOUSE, HIKING TRAILS, TENNIS AND MORE! ONLY 2 1/2 HRS FROM NY... View all property information
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    Otis, Berkshires
    1 / 6
    Becket
    2 Bedrooms, 2 Bathrooms, Sleeps 2 | Quick View
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    • Waterfront
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    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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    Becket, Berkshires
    1 / 16
    5 of 5 stars (2) Excellent
    Hancock
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Low long term rates. Call $2500/mo for 3 months. Free Electric Vehicle Charging Station! (240V 40A no J1772) Thanksgiving Special - Nov 24 - Dec 1 - $500 Christmas Special - Dec 20 - Dec 27 - $800 Ski Season Dec 1 - Mar 31 $8000 April $50/nt Summer Cultural May 26, 2014 - Seot 2, 2014 $7500 Summer... View all property information
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    Hancock, Berkshires
    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...
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    1 / 10
    5 of 5 stars (2) Excellent
    Great Barrington
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    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
    5 of 5 stars Reviewed May 20, 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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    1 / 7
    5 of 5 stars (8) Excellent
    North Adams
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Cozy cottage with complete privacy on 142 acres and borders Monroe State Forest. Cottage offers 2 bedrooms, 1 bathroom, large living room, eat in kitchen, deck with grill, TV and DVD. Hiking and biking is available right outside your door. The Dunbar Brook Trail boasts great hiking and a grove of... View all property information
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    North Adams, Berkshires
    5 of 5 stars Reviewed August 25, 2015
    Descriptions are accurate. The house and grounds are very well kept. Extremely clean especially bathroom and kitchen. It is located at the end of a hard pack dirt road with no...
    5 of 5 stars Reviewed August 24, 2015
    The minute we entered the cottage we felt at home. A perfect secluded, warm and cosy getaway. Our only sorrow was that we could only stay for one night. We prepared dinner in the...
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    1 / 29
    Lenox
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    • x
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    • x
    About this property
    AS YOU OPEN THE GATE FROM THE DRIVE YOU WALK ONTO YR FRONT DECK LEADING TO THE ENTRY , MUD ROOM WHICH HOLDS YR SUMMER NEEDS, SKIS AND BOOTS. THIS LEADS TO THE COTTAGE APT. [attached to the owner`s quarters} LIVING RM- HAS A SOFA SLEEPER TO ACCOMMODATE 2 MORE GUESTS. KITCHENETTE W/ LG CEILING... View all property information
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    Lenox, Berkshires
    1 / 17
    5 of 5 stars (2) Excellent
    Lee
    Private Room, 1 Bathroom, Sleeps 6 | Quick View
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    • Central Heating
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    • ?
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    • 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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    Lee, Berkshires
    5 of 5 stars Reviewed October 11, 2015
    Rustic and vintage are apt descriptions of the house itself. It has stories to tell! And to matched its abundant, well aged charm is the friendly and generous host. Joanne made us...
    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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    1 / 4
    Stockbridge
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    This farmhouse has 3 bedrooms available so guests may bring their family, several friends, or overlap with new ones. The Iris Room is bright and airy with 4 windows; the Nasturtium Room has a Full bed with a half bath and the Horse room has a full and single bed across from the community... View all property information
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    Stockbridge, Berkshires
    1 / 16
    5 of 5 stars (1) Excellent
    North Adams
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    Windsor Cottage is a beautiful, newly renovated lakeside retreat located on Windsor Lake in North Adams, MA. where you can enjoy your own private water access from your front lawn. You will feel like you are in the middle of the forest, yet you are in walking distance to the town, Mass MoCA and... View all property information
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    North Adams, Berkshires
    1 / 25
    Stockbridge
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • 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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    Stockbridge, Berkshires
    1 / 19
    5 of 5 stars (1) Excellent
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Sauna
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    • Pet-friendly
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    • x
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    • x
    About this property
    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. In winter, ski out your door and onto the lifts; in spring, summer and fall, enjoy hiking and horseback... View all property information
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    Hancock, Berkshires
    5 of 5 stars Reviewed September 9, 2015
    The units are clean and spacious and well stocked. Movie theater, swimming pools, outdoor picnic area with grills. and the mountain adjacent has plenty of outdoor activities...
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    1 / 20
    5 of 5 stars (2) Excellent
    Pittsfield
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    About this property
    House is very private and located on 4 acres of Land. Back yard is peaceful and overlooks ponds. The backyard has a patio/picnic area with gas grill and firepit. One of the ponds has a spurting and lighted fountain that is relaxing ...so have a campfire at night and watch the lighted fountain for a... View all property information
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    Pittsfield, Berkshires
    5 of 5 stars Reviewed May 31, 2016
    This home is meticulous, charming, cozy, comfortable and relaxing. We thoroughly enjoyed the backyard and spent hours just visiting with each other over a warm fire while the...
    5 of 5 stars Reviewed November 29, 2014
    The photos speak for themselves. Overall, the home was a great escape from city life, and included its own scenery and lake. My only complaint is that our stay was so short-lived...
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    1 / 11
    Hinsdale
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    • 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
    1 / 6
    West Stockbridge
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • ?
    • x
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    • x
    About this property
    Architect-designed, one bedroom studio cottage in peaceful setting on quiet road with a 5 acre view! What more could you ask! Perfect haven for artist or writer or anyone wanting to get away! Only 15 minutes to Tanglewood or Kripalu This little gem has just been renovated, with built in couches,... View all property information
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    West Stockbridge, Berkshires
    1 / 23
    5 of 5 stars (1) Excellent
    Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    PRIVACY-QUIET- HIKE-SKI-RELAX FYI in the winter, a huge hill behind the house on our property is fantastic for sledding . Animals you might see- Turkeys, Ducks, Bobcat, Bear, Deer, Otter, Muskrat, Heron depending on the season. A 1/4 mile driveway thru the woods takes you to 38 acres, and this... View all property information
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    Stockbridge, Berkshires
    1 / 13
    Hancock
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • 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. Near Clark Art Museum, MassMoca. Williams College with schedule of sports open to the public: swimming, tennis, squash, basketball, skating and fitness room. Indoor... View all property information
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    Hancock, Berkshires
    1 / 19
    5 of 5 stars (2) Excellent
    North Adams
    2 Bedrooms, 1 Bathroom, Sleeps 10 | Quick View
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    • Skiing: Property Is...
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    • ?
    About this property
    I have a 2 to 3 bedroom first floor apartment located in a dead end street. This spacious 8 room apartment is surrounded by woods and minutes from downtown North Adams or Williamstown!! It is also walking distance to Mass MoCa (about a 10 minute walk)!!! Animals are welcome if needed. The master... View all property information
    Location Information
    North Adams, Berkshires
    5 of 5 stars Reviewed September 11, 2015
    Owners were very friendly and helpful. We enjoyed our stay very much. this is the place for a quiet vacation.
    5 of 5 stars Reviewed July 6, 2014
    Stephanie was helpful and accommodating of us and our last minute request . Sheafs it easy to stay, come and go and we found the location convenient yet private and remote from...
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    1 / 46
    5 of 5 stars (1) Excellent
    Lee
    5 Bedrooms, 6 Bathrooms, Sleeps 20 | Quick View
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    • Pet-friendly
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    • x
    About this property
    In the heart of the Berkshires: near Tanglewood, Jacob's Pillow, Jiminy Peak, Ski Butternut, Lenox MA, Stockbridge MA. Completely restored historic house with fully equipped kitchen, 5 bedrooms (each with a private bathroom), 3 spacious common rooms. A comfortable place for a family reunion,... View all property information
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    Lee, Berkshires
    5 of 5 stars Reviewed May 29, 2016
    My family loved this house - parents and kids, all found it comfortable, spacious, and welcoming. Host is accommodative on last-minute changes or special requests. Easy...
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    1 / 8
    Lenox
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • x
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    • x
    About this property
    Great little house in a very convenient location. Set nicely back from the street with a spacious back and side yard. 8 minutes drive to tanglewood. All rooms are furnished. Living room with bay window and fireplace, hardwood floors throughout. Almost an acre of land with large trees and garden.... View all property information
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    Lenox, Berkshires
    1 / 12
    5 of 5 stars (21) Excellent
    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • ?
    • ?
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    • 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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    Great Barrington, Berkshires
    5 of 5 stars Reviewed August 5, 2016
    What a charming, relaxing, and peaceful rental in the very heart of Berkshires cultural activities and venues. The view and pool are splendid, the apartment itself is private...
    5 of 5 stars Reviewed July 26, 2016
    From the lawn of the cottage, one looks down on farms, meadows, and mountains. The sky is so big, I thought I was in Montana. One step out the door and you're walking on rambling...
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    1 / 7
    Lee
    Private Room, 1 Bathroom, Sleeps 6 | Quick View
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    • ?
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    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
    1 / 14
    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • ?
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    • x
    About this property
    One bedroom, one bathroom cottage on beautiful country road. Private garden and screened-in porch. Two miles to shops and restaurants of downtown Great Barrington. Enjoy nearby skiing, cycling, fishing, hiking and golf.<BR><BR>The Space:<BR><BR>Quaint cottage with wood burning stove. Ideal base for... View all property information
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    Great Barrington, Berkshires
    1 / 19
    5 of 5 stars (4) Excellent
    Lee
    5 Bedrooms, 6 Bathrooms, Sleeps 9 | Quick View
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    • x
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    • x
    About this property
    Custom designed Furnished Lake House in The Berkshires in Massachusetts on the Lee/Lenox line. Gorgeous western sunsets ! The home has 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
    5 of 5 stars Reviewed 3 weeks ago
    My family and I traveled to the Berkshires from Boston and stayed in this gorgeous lake house. We had booked vacation rentals in the past and had a whole range of experiences from...
    5 of 5 stars Reviewed 4 weeks ago
    We stayed at the Lake House on beautiful Laurel Lake with my family of 5 (two daughters, son, and my wife). We had an awesome time. The owners Marjorie and Frank were wonderful...
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