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Vacation Rentals in Richmond, MA and nearby

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    1 / 10
    4.5 of 5 stars (6) Very good
    Richmond
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    $135
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    Richmond
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    $450
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    The following rentals are within 10 miles of Richmond, Massachusetts.

    Lee
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    $100
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    1 / 35
    4 of 5 stars (8) Very good
    Lee
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    $365
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    Amenities & Details
    • Mountain Views
    • Central Heating
    • DVD Player
    • Grill
    • Washer
    • Porch
    • Outdoor Dining Area
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • 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
    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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    Lenox
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    other traveler has booked this property
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    $400
    / Night
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    • Sauna
    • Mountain Views
    • Hot Tub
    • Air Conditioning
    • Internet Access
    • Shared Indoor Pool
    • DVD Player
    • Satellite TV
    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
    Location Information
    Lenox, Berkshires 01240
    1 / 8
    5 of 5 stars (2) Excellent
    West Stockbridge
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travelers have booked this property
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    $125
    / Night
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    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Parking
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    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 01266
    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...
    5 of 5 stars Reviewed November 26, 2013
    Beautiful, modern and cosy home which proved to be a great base for the trip! The fire was an added treat at the end of the day! Location wise the cottage was perfect - close to...
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    1 / 9
    Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    From
    $400
    / Night
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    Amenities & Details
    • Air Conditioning
    • Washer
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Beautifully appointed farm house situated on 200 acres of this pristine estate located in the heart of the Berkshires. This home offers three bedrooms, three bathrooms, fully equipped kitchen, laundry room, deck and porch. Perfectly located to all The Berkshires attractions, This home is within 4... View all property information
    Location Information
    Stockbridge, Berkshires
    1 / 48
    Lee
    6 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
    From
    $1,514
    / Night
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    Amenities & Details
    • Balcony
    • Satellite TV
    • Patio
    • Washer
    • Central Heating
    • Waterfront
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Chanterwood is an expansive, light-filled modern home with the luxuries one expects today in a lakefront estate blended with the comfort, casualness and intimacy of its' 100-year old Inn heritage. Chanterwood is newly available for summer 2016 - illness forced tenants to cancel summer plans... View all property information
    Location Information
    Lee, Berkshires 01238
    East Chatham, NY
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    From
    $165
    / Night
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    Amenities & Details
    • Air Conditioning
    • Outdoor Dining Area
    • Wi-Fi
    • DVD Player
    • Patio
    • Mountain Views
    • Grill
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Our cottage has been lovingly maintained and is in pristine condition. It is also very well laid out. You will enter through a generous foyer with closet and antique breakfront, and pass the media room (optional 3rd bedroom) with a divided light glass wall separating it from the family room. The... View all property information
    Location Information
    East Chatham, New York 12060
    1 / 12
    4 of 5 stars (1) Very good
    Lenox
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other traveler has booked this property
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    $250
    / Night
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    Amenities & Details
    • Internet Access
    • Balcony
    • DVD Player
    • Grill
    • Washer
    • Central Heating
    • Porch
    • Mountain Views
    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
    Location Information
    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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    1 / 16
    4.5 of 5 stars (3) Very good
    Stockbridge
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    other travelers have booked this property
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    $150
    / Night
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    • Wi-Fi
    • Shared Yard
    • Patio
    • Air Conditioning
    • Outdoor Dining Area
    • Waterfront
    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
    Location Information
    Stockbridge, Berkshires 01262
    5 of 5 stars Reviewed July 13, 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 June 21, 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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    Lee
    1 Bedroom, 2 Bathrooms, Sleeps 5 | Quick View
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    $155
    / Night
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    Amenities & Details
    • Grill
    • Patio
    • Shared Yard
    • Parking
    • Mountain Views
    • Wi-Fi
    • Private Yard
    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
    Location Information
    Lee, Berkshires 01238
    Austerlitz, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travelers have booked this property
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    $200
    / Night
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    Amenities & Details
    • Grill
    • Washer
    • Parking
    • Shared Yard
    • Internet Access
    • Mountain Views
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This 3 Bedroom 2.5 bathroom recently constructed home sits on 40 wooded, secluded acres in Austerlitz, Columbia County, just 4 miles from the Massachusetts border. It offers stunning views of the Catskills, peace and quite and plenty of nature to watch from the back porch. Chatham, NY is 15 minutes... View all property information
    Location Information
    Austerlitz, New York 12017
    1 / 11
    4 of 5 stars (2) Very good
    Lee
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    From
    $250
    / Night
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    Amenities & Details
    • Mountain Views
    • Internet Access
    • Parking
    • Satellite TV
    • Grill
    • DVD Player
    • Washer
    • 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
    Location Information
    Lee, Berkshires 01238
    4 of 5 stars Reviewed June 17, 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...
    4 of 5 stars Reviewed September 24, 2010
    The house is comfortable, clean, and convenient to Lenox, Stockbridge, and the rest of the Berkshires. Traffic from the street can be a bit loud at times, but it quiets down at...
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    1 / 11
    3.5 of 5 stars (3) Average
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other travelers have booked this property
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    $225
    / Night
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    Amenities & Details
    • Grill
    • Central Heating
    • Internet Access
    • Washer
    • Satellite TV
    • Mountain Views
    • Waterfront
    • DVD Player
    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
    Location Information
    Stockbridge, Berkshires 01262
    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...
    3 of 5 stars Reviewed July 4, 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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    1 / 17
    5 of 5 stars (2) Excellent
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
    other traveler has booked this property
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    $450
    / Night
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    Amenities & Details
    • Central Heating
    • Grill
    • Internet Access
    • Parking
    • Mountain Views
    • Hot Tub
    • Outdoor Dining Area
    • Washer
    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
    Location Information
    Lee, Berkshires 01238
    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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    Lee
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    From
    $299
    / Night
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    • Air Conditioning
    • DVD Player
    • Terrace
    • Balcony
    • Washer
    • Secure Parking
    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
    Location Information
    Lee, Berkshires 01238
    1 / 14
    5 of 5 stars (5) Excellent
    West Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    $300
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    • Mountain Views
    • Wi-Fi
    • Balcony
    • Patio
    • Grill
    • Washer
    • Porch
    • Central Heating
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • 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
    Location Information
    West Stockbridge, Berkshires 01266
    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...
    5 of 5 stars Reviewed August 25, 2014
    We were excited to get away from NYC and stay in the Berkshires! It was a wonderful stay at this home! So spacious, comfortable, lots of thoughtful gestures for our stay! We...
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    Canaan, NY
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    From
    $100
    / Night
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    • Parking
    • Balcony
    • Air Conditioning
    • Grill
    • Outdoor Dining Area
    • Porch
    • Wi-Fi
    • Terrace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    A cute cabin in the woods with easy access to a lake a short 500 ft walk down a dirt road. Swimming is available at a private member beach by either canoe or a sort drive to the other end of the the Lake. Convenient to the Berkshires. Tanglewood is a 15 min drive and Jacob's Pillow and Saratoga... View all property information
    Location Information
    Canaan, New York 12029
    1 / 19
    5 of 5 stars (19) Excellent
    West Stockbridge
    5 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    $250
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    • Central Heating
    • Grill
    • Internet Access
    • Patio
    • Satellite TV
    • DVD Player
    • Mountain Views
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • 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
    Location Information
    West Stockbridge, Berkshires 01266
    5 of 5 stars Reviewed 4 weeks ago
    Elaine was great! She may be the nicest person I have ever met. She was very accommodating, warm, and laid back; responsive to our needs, without ever being intrusive. House was...
    5 of 5 stars Reviewed October 20, 2015
    Elaine was a great hostess! We enjoyed her house immensely. It was fully equipped, clean and very comfortable. Very close to many quaint little towns. We look forward to a...
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    1 / 12
    5 of 5 stars (3) Excellent
    Alford
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    $125
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    • Hot Tub
    • Mountain Views
    • Satellite TV
    • Waterfront
    • DVD Player
    • 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
    Location Information
    Alford, Massachusetts 01266
    5 of 5 stars Reviewed May 2, 2013
    The Smith Homestead is a fantastic get-away for those looking to get peace and quiet in the picturesque Berkshire community of alford. The drive up to alford was both easy and...
    5 of 5 stars Reviewed April 10, 2013
    Set back in the Berkshires, Alford Ma is a stone's throw from New York State. The small town borders Great Barrington, which is rich in activity. Many famous americans have...
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    Stockbridge
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    $225
    / Night
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    • Washer
    • Parking
    • Patio
    • Grill
    • 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
    Location Information
    Stockbridge, Berkshires 01262
    1 / 24
    5 of 5 stars (2) Excellent
    Lee
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
    From
    $1,650
    / Week
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    • Parking
    • DVD Player
    • Satellite TV
    • Washer
    • Hot Tub
    • Internet Access
    • Porch
    • 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
    Location Information
    Lee, Berkshires 01238
    5 of 5 stars Reviewed February 21, 2012
    I didn't want to leave. It was the most relaxing and tranquil time I could have imagined. The house is lovely and extremely comfortable -- clean, cozy and situated close to a...
    5 of 5 stars Reviewed February 12, 2012
    We had the most amazing time. This adorable home is so close to everything and yet is feels very private and secluded. It provided a perfect balance for relaxation and adventure...
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    Lee
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    $375
    / Night
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    • Sauna
    • Air Conditioning
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Indoor Pool
    • Mountain Views
    • DVD Player
    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
    Location Information
    Lee, Berkshires 01238
    1 / 24
    5 of 5 stars (23) Excellent
    Lee
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    $350
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    • Wi-Fi
    • Grill
    • Washer
    • Satellite TV
    • Mountain Views
    • Patio
    • DVD Player
    • Air Conditioning
    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
    Location Information
    Lee, Berkshires 01260
    5 of 5 stars Reviewed 1 week ago
    My wife, daughters and their husbands spent a winter weekend in the Berkshires, where we skied, visited local venues and enjoyed Great Barrington's restaurants. As a home base...
    5 of 5 stars Reviewed 2 weeks ago
    Our large group -- 6 adults, 2 babies, and a dog -- met at the School House for MLK weekend and had a fantastic time. It was our third visit to Mary's house and each has been...
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    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    $500
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    Vacation home centrally located in the Berkshires, 1 mile from Norman Rockwell and 3 miles from Tanglewood, on a quiet country road. Spacious grounds with large 2-level deck overlooking gardens and woods, private in-ground pool with pool house and deck, hot tub. House includes 3 bedrooms, 2 newly... View all property information
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    Stockbridge, Berkshires 01262
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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
    South Lee
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Two Bedroom two bathroom condo located on beautiful resort in the Berkshires. Oak and Spruce Resort located 15 minutes to Tanglewood is the summer home in the Berkshires of the Boston Symphony Orchestra. Condominium sleeps 6 with an eat in kitchen and living area. Recreational activities, ample... View all property information
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    South Lee, Berkshires 01260
    Austerlitz, NY
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    Newly built cabin in the woods. The cabin is perfect for a small family or couple. It is a perfect location for wanting to be close to the Berkshires, Hudson NY, and Copake Lake. Tons of hiking trails and swimming lakes for the summer and minutes from Butternut and Catamount ski resorts in the... View all property information
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    Austerlitz, New York 12017
    West Stockbridge
    5 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    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 01266
    1 / 8
    4 of 5 stars (2) Very good
    Pittsfield
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    • Satellite TV
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    • x
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    About this property
    A Fully-Furnished Extended Stay property in the Berkshires. Located across the street from the Colonial Theatre and within minutes of most Berkshire County attractions. Each spacious, efficiency (condo-style) single bedroom apartment includes living room, kitchen with full size appliances,... View all property information
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    Pittsfield, Berkshires 01201
    3 of 5 stars Reviewed August 17, 2015
    The place was less than ideal in that the room smelled of smoke when we walked in. The bedroom had no windows and that felt very claustrophobic. It did have a kitchen which was...
    5 of 5 stars Reviewed July 3, 2013
    WOW, this place was very nice! What you get is a place with a five minute walk from downtown, well kept buidlings and grounds, excellent floor plans, new furniture, modern...
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    1 / 18
    5 of 5 stars (2) Excellent
    Lee
    5 Bedrooms, 6 Bathrooms, Sleeps 9 | Quick View
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    • Pet-friendly
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    • x
    • x
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    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
    5 of 5 stars Reviewed October 29, 2015
    The Lake House was paradise. It is situated right in The Berkshires on Rte. 20 with easy access to everything. We golfed, canoed, played tennis, swam, hiked, went to museums...
    5 of 5 stars Reviewed October 27, 2015
    We were a group of 8 friends who have vacationed together annually. This was by far the best appointed house we have rented in 30 years. The owners, Margie and Frank were...
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    Lenox
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    $950
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    • Pet-friendly
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    • x
    • x
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    About this property
    Just steps to Tanglewood Main Gate and Kripalu from this dramatic three-story shingle style contemporary with five bedrooms and five and a half baths. The six hundred square foot great room has a soaring ceiling, fireplace, interior balcony, and multiple French doors and windows to overlook the... View all property information
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    Lenox, Berkshires 01240
    Lee
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    see better & more photos of property here (copy-paste-edit in browser): tinyurl DOT com/hoqrp7n 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... View all property information
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    Lee, Berkshires 01238
    1 / 19
    4.5 of 5 stars (28) Very good
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    $199
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    • Satellite TV
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    • x
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    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
    Location Information
    Stockbridge, Berkshires 01262
    5 of 5 stars Reviewed November 7, 2015
    The house was beautiful. We stayed with two of our children--a young man and a teenager. There was plenty of room for all of us. The breakfast was wonderful. The immediate...
    4 of 5 stars Reviewed August 13, 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...
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    Lee
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    $750
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    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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    Lee, Berkshires 01238
    1 / 8
    5 of 5 stars (1) Excellent
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Hot Tub
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    • x
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    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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    South Lee
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    Close to ski resorts, cross country skiing, restaurants, and all the cultural offerings of the Berkshires. The Berkshire region is a year-round destination for vacationers, so the Oak N’ Spruce Resort offers guests a selection of amenities to keep them coming back no matter what season. The... View all property information
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    South Lee, Berkshires 01260
    1 / 2
    5 of 5 stars (1) Excellent
    Lee
    1 Bedroom, 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
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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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    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • 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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    Stockbridge, Berkshires 01262
    1 / 20
    5 of 5 stars (1) Excellent
    Pittsfield
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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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 01201
    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 / 16
    5 of 5 stars (5) Excellent
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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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 01262
    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 / 21
    5 of 5 stars (21) Excellent
    Lenox
    4 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    • ?
    • x
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    • x
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    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 2 weeks ago
    My friends and I loved the Gartner home. It was conveniently located to downtown Lenox, cozily furnished and spotlessly clean. The eat in kitchen was well stocked with everything...
    4 of 5 stars Reviewed October 16, 2015
    We were here during the 2015 foliage season. Absolutely beautiful. The house was very roomy and very comfortable. Has all the amenities you need in kitchen and other rooms...
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    West Stockbridge
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • ?
    • x
    • x
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    • x
    • 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 12029
    1 / 13
    5 of 5 stars (2) Excellent
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    $250
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    • x
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    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
    Location Information
    Stockbridge, Berkshires 01262
    5 of 5 stars Reviewed May 26, 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 January 22, 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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    1 / 23
    5 of 5 stars (1) Excellent
    Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    $500
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    • Washer
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    • Mountain Views
    • Waterfront
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    • Pet-friendly
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    • Child-friendly
    • x
    • x
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    • x
    About this property
    A home for the family: SKIING, SNOWSHOEING, AND SLEDDING. Fall and Winter availability. Behind the house, on the property is a HUGE hill that is great for sledding. 12 mins to Butternut. 25 mins to Jiminy. Across the road is a park that is great fun to hike, snowshoe, CC ski, and explore. A... View all property information
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    Stockbridge, Berkshires 01260
    5 of 5 stars Reviewed May 18, 2010
    This house had it all... my wife and I loved our time there. During the day we would either sit on the deck and read or go swimming in our own private lake that was very, very...
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    Lenox
    2 Bedrooms, 1 Bathroom, Sleeps 4 | 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
    Location Information
    Lenox, Berkshires 01240
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    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
    Location Information
    Lee, Berkshires 01238
    Lenox
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    $250
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    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
    Location Information
    Lenox, Berkshires 01240
    New Lebanon, NY
    5 Bedrooms, 5 Bathrooms, Sleeps 5 | Quick View
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    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
    Location Information
    New Lebanon, New York 12125