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Holiday Apartments in Spencertown

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    All 46 Rentals in Spencertown
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    Spencertown
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    The following rentals are within 15 kilometres of Spencertown.
    Great Vacation House in the Berkshires on Richmond Pond1 / 10
    (4)Excellent
    Richmond, MA
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Comfortable Farmhouse in the Berkshires1 / 10
    (4)Excellent
    West Stockbridge, MA
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    RiverSong Suite In The Berkshires1 / 52
    (14)Excellent
    North Egremont, MA
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Patio
    • Air Conditioning
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 2018
    We eagerly anticipated our stay at RiverSong. Based on the plethora of five-star reviews we expected near-perfection. While we loved the atmosphere, fabulous comfortable bed...
    Reviewed 3 November 2017
    Riversong suite was wonderful, situated in a great location. Close to nearby restaurants and shops yet far from all the noise. Peaceful and quiet. A great place to renew...
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    About this property
    Located in the Berkshire mountains on more than 5 acres surrounded by 29 acres of conservation land. Featuring beautiful views of meadows, mountains and farm land bordering the crystal clear Green River (great trout fishing).Only 10 minutes from Great Barrington's Main Street stores, resturaunts,...
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    01230, North Egremont, Berkshires
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    North Egremont, MA
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Mountain Views
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our nearly new home we call RiverSong is on 5.5 acres surrounded by almost 30 more conservation land of meadow and farmland. The pristine Green River is right in our back yard with a wonderful swimming hole. Our Penthouse room is on the upper level of our home. A Bright and spacious king size...
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    01230, North Egremont, Berkshires
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Beautifully decorated & immaculate log chalet1 / 26
    (16)Excellent
    Hillsdale
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Mountain Views
    • Air Conditioning
    • Washer
    • Grill
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 July 2018
    Log cabin was beautiful, very clean, well stocked, and in great condition. Cabin is centrally located and convenient to all the Berkshires have to offer. It was perfect for our...
    Reviewed 22 November 2017
    second year in a row i stayed here with family.fantastic place and immaculately kept.will be booking my stay every year.thanks Bill
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    About this property
    3 bedrooms, 2 full baths, living room, dining room, kitchen, loft area. Private and secluded log cabin chalet is situated on three picturesque acres overlooking tall pines and forests with heartwarming winter mountain views. The chalet was built in 2003 and has gorgeous stone countertops and two...
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    12529, Hillsdale, New York
    Cabin Holiday Rental - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Stockbridge Bowl Lake Beach Cottage near Tanglewood (1.8 miles away)1 / 17
    (1)Excellent
    Stockbridge, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Mountain Views
    • Balcony
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 July 2018
    Great location, 2 minute walk to the beach with a view of the mountains and a very short drive to Tanglewood, Norman Rockwell Museum and all local attractions.Cindy and Paul are...
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    About this property
    The Stockbridge Bowl Lake Beach cottage is centrally located in Berkshire County in Stockbridge, MA. Walk across the street to Stockbridge Bowl Town Beach. We provide the beach chairs and towels. Lovely furnishings, fully equipped kitchen with new small appliances and amenities. Open cottage feel...
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    Location Information
    01262, Stockbridge, Berkshires
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Richmond, MA
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Mountain Views
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This vacation home has something for everyone! If you're a culture vulture, outdoor enthusiast, or just want the peace and quiet of the country, this 4 bedroom home in the Berkshires is for you! It is 15 minutes from Lenox and Tanglewood, 10 minutes from shopping, restaurants and several theatres,...
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    01254, Richmond, Berkshires
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Plan your holidays in the Berkshires. Forecasting plenty of snow and mild temps.1 / 18
    (7)Excellent
    West Stockbridge, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
    • Wi-Fi
    • Balcony
    • Patio
    • Grill
    • Washer
    • Porch
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 September 2018
    The house was so comfortable; the location was perfect -- close to so many beautiful places and Berkshires attractions, especially Tanglewood!; Cassandra was so helpful when I...
    Reviewed 27 August 2016
    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...
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    About this property
    Located in West Stockbridge minutes from everything . Nestled in the Berkshire Mountains. Convenient yet Private. 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 a destination, a haven, a state...
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    01266, West Stockbridge, Berkshires
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Austerlitz
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Washer
    • Hot Tub
    • Central Heating
    • Balcony
    • Grill
    • Patio
    • Mountain Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The beautiful renovated Georgian Colonial home sits amongst 40 acres of natural beauty. The house overlooks a serene pond and all its beauty with views of natural forrest beyond. The house itself has a oversized chef's eat in kitchen. The Kitchen has all the amenities to host wonderful meals and...
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    Location Information
    12017, Austerlitz, New York
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    Beautiful Vacation Home1 / 32
    (5)Excellent
    Stockbridge, MA
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Mountain Views
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Patio
    • Sauna
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 February 2017
    Our 4 families stayed here for a long ski weekend and had the best time! The home is beautiful-- and had plenty of space for all of us! The home was fully stocked with...
    Reviewed 10 November 2016
    Excellent experience. Very spacious and beautiful. Amazing backyard woods. Beautiful scenery within and around the town. Very attentive owners.
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    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...
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    Location Information
    01262, Stockbridge, Berkshires
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    West Stockbridge, MA
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 room, fall foliage and scenic atmosphere in the area, and soak in the...
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    Location Information
    01266, West Stockbridge, Berkshires
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Berkshire Farmhouse Vacation1 / 20
    (36)Excellent
    West Stockbridge, MA
    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Central Heating
    • Grill
    • Internet Access
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Mountain Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 February 2018
    We had a large group staying at the house with kids and had a great experience. Elaine is very thoughtful, helpful and attentive. She obviously cares about the house and makes...
    Reviewed 14 November 2017
    Elaine was a pleasure to communicate with and made us feel right at home. The home is just how it looks in the pictures. If you're searching for a comfortable, clean, and cozy...
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    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,...
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    Location Information
    01266, West Stockbridge, Berkshires
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 12
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    The Smith Farm Homestead1 / 12
    (6)Excellent
    Alford, MA
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Hot Tub
    • Mountain Views
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 October 2018
    This was a perfect place for a bit of R & R. Friendly owners and luxurious room that was clean and comfortable. The home has a historical atmosphere in a beautiful country...
    Reviewed 4 February 2017
    Cozy and pretty room and bathroom suite that I shared with my teenaged daughter. Susan is very welcoming and friendly. We loved our stay here and would return!
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    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...
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    Location Information
    01266, Alford, Berkshires
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Old Chatham
    8 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Hot Tub
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Housekeeping Included
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Berkshire Country Estate is located on 60 acres in the foothills of the Berkshires, only 2 1/2 hours from New York City and Boston. Surrounded by the beauty of the Berkshires, the estate is very private, with a 1/8 mile driveway leading to the 10 acre front lawn. A large elegant, yet...
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    Location Information
    12136, Old Chatham, New York
    Holiday Rental House - 8 Bedrooms, 5 Bathrooms, Sleeps 16
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    Stockbridge, MA
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Parking
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THE ESCAPE at Stockbridge. Enjoy our Open & Spacious Newly built house in the Berkshires, Complete Privacy! No Visible Neighbors. -1 1/2 miles to downtown Stockbridge, -just minutes to Norman Rockwell museum, Chesterwood, Naumkeag, Tanglewood & Kripalu. -Housatonic River just across the street,...
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    Location Information
    01262, Stockbridge, Berkshires
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    Family-friendly Cottage Near Lake, Tanglewood1 / 16
    (6)Excellent
    Stockbridge, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Cable/satellite TV
    • Porch
    • Parking
    • Washer
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 August 2017
    Location was fantastic. Sarah (the owner) provided some great advice on local farmers markets and hikes. The beach was a quick walk from the cottage where we could paddle on...
    Reviewed 31 July 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...
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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...
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    01262, Stockbridge, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Stockbridge, MA
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Mountain Views
    • Air Conditioning
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THIS CUSTOM BUILT HOME is a one-of-a-kind, must see getaway retreat that is beautifully furnished, and meticulously maintained. The entire first floor 'guest suite' was designed to accommodate friends or extended family. The upper level is the main floor with an open plan kitchen, dining room, and...
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    01262, Stockbridge, Berkshires
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Cozy & Modern Home -mins from Tanglewood & Kripalu1 / 8
    (2)Excellent
    West Stockbridge, MA
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 December 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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    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...
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    Location Information
    01266, West Stockbridge, Berkshires
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Berkshire Country Estate - The Library Suite1 / 21
    (1)Excellent
    Old Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 September 2018
    We were looking for a one night stay while in the neighbourhood. We could not have asked for a better place. This amazing house will take you away from everyday business and...
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    About this property
    The beautiful Berkshire Country Estate is located on 60 acres in the foothills of the Berkshires, minutes from Lenox MA & Hudson NY, less than a 2 1/2 drive from New York City. Library Suite: Luxuriate in our spacious two room suite to accommodate 2-4 guests with fireplace, full bath w/ deep soak...
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    Location Information
    12136, Old Chatham, New York
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Hillhouse Log Cabin1 / 18
    (1)Excellent
    Hillsdale
    3 Bedrooms, 2 Bathrooms, Sleeps 13 Quick View
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    • Cable/satellite TV
    • Waterfront
    • Mountain Views
    • Washer
    • Grill
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cozy modern log cabin nestled in the Berkshires in a large wooded area with landscaped yard on a small river. The cabin has a full service kitchen and a great room with dining and lounging space. There is a full entertainment center with furnished recorded music and movies. Bedrooms and bath are...
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    12529, Hillsdale, New York
    Cabin Holiday Rental - 3 Bedrooms, 2 Bathrooms, Sleeps 13
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    Ghent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Mountain Views
    • Air Conditioning
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will be enjoying a newly renovated space with Calcutta marble floors throughout. The house features 2 bedrooms at opposite sides of the house to provide more privacy. A luxurious bathroom with a Roman soaking tub and marble mosaics. A totally loaded kitchen and great outdoor space which...
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    12075, Ghent, New York
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Stockbridge, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Patio
    • Grill
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    01238, Stockbridge, Berkshires
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Stockbridge, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completely renovated vacation home with state of the art kitchen and marble baths, centrally located in the Berkshires 3 miles from Tanglewood, on 10 acres on a quiet country road. New in-ground pool surrounded by patio and expansive deck and pool house nestled in the woods. Central air...
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    Location Information
    01262, Stockbridge, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Overnight at Althouse -Higgins1 / 11
    (3)Excellent
    Hillsdale
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Parking
    • Wi-Fi
    • DVD Player
    • Mountain Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 January 2017
    Great, clean property. Plenty of space and privacy for a family of 4. Kitchen and apt. well stocked (linens, towels, etc). Everything you need from a store is within 1,000 feet...
    Reviewed 4 November 2015
    C'était tellement bien, que j'ai déjà envie d'y retourner!!As a French citizen, I can affirm that my stay at Lynne and Bill's loft was perfect! No noise, comfortable and with...
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    About this property
    We found a great circa 1845 house in the Berkshire/Taconic Mtn area and fully renovated the entire building creating retail shops and a sophisticated but casually comfortable 2 BR apt. saving many of the original building features. Fully equipped efficiency kitchen with a W/D, marble bath, sleeps 6...
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    12529, Hillsdale, New York
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Restored 1886 Eyebrow Colonial1 / 17
    (1)Excellent
    Stockbridge, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
    • Patio
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Washer
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 January 2017
    Our family of four absolutely loved our stay in Melanie and Henry's home. After communicating with Melanie before our arrival, we felt welcome before we stepped into the house...
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    About this property
    Explore the culture and natural beauty of the Berkshires while vacationing in a completely restored colonial home with modern amenities. You will be central to all the wonderful cultural attractions and outdoor activities in the area. Walk to the quaint town of Stockbridge and the Norman Rockwell...
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    Location Information
    01262, Stockbridge, Berkshires
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Newly Renovated Colonial on the River! Sleeps 5-61 / 20
    (1)Excellent
    Stockbridge, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Internet Access
    • Patio
    • Waterfront
    • Central Heating
    • Cable/satellite TV
    • Porch
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Blue House on the Bend Newly renovated historic eyebrow colonial located on an idyllic bend of the Housatonic river comfortably accommodates 5 or 6 people. Built around 1820, the Blue House on the Bend has been updated and outfitted for modern day convenience but retains its charm and unique...
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    Location Information
    01236, Stockbridge, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Chatham
    4 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Patio
    • Terrace
    • Housekeeping Included
    • Balcony
    • Central Heating
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fully renovated 1800s farm house on 100 acres with heated in ground gunnite pool, hiking trails located on a beautiful creek. We also have a guest house with two more bedrooms and a full kitchen by the pool that is perfect for bringing your in-laws or babysitter. The house has a chef's kitchen...
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    Location Information
    12037, Chatham, New York
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 6
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    NEW! 'Butterfly Hill' 2BR West Stockbridge House1 / 24
    (1)Excellent
    West Stockbridge, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Mountain Views
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Patio
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 August 2018
    We thoroughly enjoyed our week at Butterfly Hill. It was near Tanglewood, our main reason for the visit, and all the nearby towns where we found good restaurants and shops. We...
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    About this property
    Boasting 3-acres of beautiful, private land, this 2-bedroom, 1.5-bathroom vacation rental house is nestled in a serene environment, offering pastoral and mountain views. With accommodations for 4, this West Stockbridge home combines comfort and gorgeous scenery to provide the perfect...
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    Location Information
    01266, West Stockbridge, Berkshires
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Richmond, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Porch
    • Internet Access
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    01254, Richmond, Berkshires
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Berkshire Getaway at 'Tofu'S Retreat'1 / 22
    (1)Excellent
    Alford, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 May 2017
    The screen door to the patio stuck a little. That's it. Period. Otherwise, this place was perfect! Three adults (two seniors), two children, and one dog spent a spectacular week...
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    About this property
    Wonderful Alford upscale family home with in ground heated pool; art barn, acreage; lush view & privacy. Private tranquil getaway vacation home.Delightful tri-level saltbox which has been completely, thoughtfully & tastefully renovated with every comfort in mind. Main floor: Enters into a breath...
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    Location Information
    01266, Alford, Berkshires
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Hillsdale
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    About this property
    This extremely private luxury home is situated on 48-acres at the end of a cul de sac and is located two miles from NY Route 22 in Columbia County just 10 minutes from the Massachusetts boarder and 30 minutes from the Vermont border. Recently renovated, this contemporary home with 5 bedrooms...
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    Location Information
    12529, Hillsdale, New York
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    Tranquil 3BR Stockbridge House w/Private Deck1 / 30
    (2)Excellent
    Stockbridge, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 July 2017
    The degree of care of the owners to assure a pleasant experience was incredible! There was a many page guide to the house, the property and the surrounding area. It...
    Reviewed 24 October 2016
    Awesome setting and a great outside porch complete with herb gardens(2). The forest around the property just invites a hike. Every possible thing was thought of by these...
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    About this property
    Elevate your Stockbridge experience by staying at this 3-bedroom, 1.5-bath vacation rental house, which sleeps 6 and boasts a private deck. Nestled within the serene forests of the Berkshires, ‘The Redway House’ is the quintessential setting for your next Massachusetts retreat. THE PROPERTY...
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    Location Information
    01262, Stockbridge, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Austerlitz
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Washer
    • Parking
    • Shared Garden
    • Internet Access
    • Mountain Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    12017, Austerlitz, New York
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    North Egremont, MA
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Private Outdoor Pool (Unheated)
    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Book a one-of-a-kind stay in this 5-bedroom, 4.5-bathroom vacation rental home in South Egremont. Built from the bones of a 15th-century British barn, this 4,000-square-foot home for 10 is one of the oldest structures in Massachusetts! Whether you were drawn to the Berkshires by the natural beauty...
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    Location Information
    01258, North Egremont, Berkshires
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    nesteldown pet friendly1 / 5
    (1)Excellent
    Old Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • DVD Player
    • Grill
    • Waterfront
    • Patio
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 November 2015
    This was such a great place for us to stay , it had everything , even went fishing - biking , the house was just perfect , we even had friends over and we had plenty of room...
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    About this property
    'One of a kind' listing. Gated , 4BR Elegant Colonial Estate on Pristine River/stream in most desirable area in Columbia County. Set in sleepy upscale Historic Hamlet on Park-like grounds. Bordered by over 150 acres of fields with Sunset views. The best Swimming , fantastic Fishing, stone Campfire...
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    Location Information
    12136, Old Chatham, New York
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Philmont
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Secure Parking
    • Air Conditioning
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the center of Columbia County, NY this retreat is a great spring board to all it has to offer: minutes to Hudson, Chatham, High Falls, hiking trails, farms, streams. You’ll love the varied bright cozy rooms to lounge in, including a screened front porch. Most relaxing is to hang out on...
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    Location Information
    12534, Philmont, New York
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
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    Old Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on 60 acres in the foothills of the Berkshires, minutes from Lenox MA & Hudson NY, less than a 2 1/2 drive from New York City. It is an elegant, yet comfortable family Georgian estate, privately sited with a long driveway and a 10 acre front lawn. Luxuriate in the Rose Suite, a nearly 1,100...
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    Location Information
    12136, Old Chatham, New York
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Stockbridge, MA
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Grill
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Private Garden
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    **1 week minimum July & August** Just 1 1/2 to the Red Lion Inn in Downtown Stockbridge, Tanglewood, Norman Rockwell Museum, Private country setting just across from the Housaitonic River. Our newly built home pairs a traditional shingle style exterior with an open & slightly modern interior. The...
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    Location Information
    01262, Stockbridge, Berkshires
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Stockbridge, MA
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Internet Access
    • Private Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The 1762 farmhouse has 3 bedrooms available to bring your family and friends enjoy the close proximity to Tanglewood, Norman Rockwell Museum, and several lakes, many hiking areas, great restaurants. Larry makes a fresh egg breakfast which is included in your stay. You can join us for horseback...
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    Location Information
    01262, Stockbridge, Berkshires
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Canaan
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Balcony
    • Air Conditioning
    • Grill
    • Outdoor Dining Area
    • Porch
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    12029, Canaan, New York
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Stockbridge, MA
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Private Garden
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 1762 farmhouse features wide board floors, kitchen, dining and living room areas along with a spacious front porch. Agritour gardens, horseback riding, and close proximity to Tanglewood and the Norman Rockwell Museum make for an adventure filled visit. Larry prepares a great fresh egg...
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    Location Information
    01262, Stockbridge, Berkshires
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Stockbridge, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Explore the culture and natural beauty of the Berkshires while vacationing in a completely restored colonial home with modern amenities in Stockbridge. This quaint vacation rental home features 2 bedrooms and 2 bathrooms, accommodating 6 guests. From this property, you'll be central to all the...
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    Location Information
    01262, Stockbridge, Berkshires
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    West Stockbridge, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Washer
    • Balcony
    • Air Conditioning
    • Housekeeping Included
    • Mountain Views
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We offer two bedrooms accessible via a private staircase in our recently renovated Victorian farm house located on two beautifully landscaped acres with seasonal gardens and adjoining woods and fields. Each bedroom sleeps 2; they can be booked individually or together at $105/bedroom/night. We...
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    Location Information
    01266, West Stockbridge, Berkshires
    Private Room - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Hudson Valley Cottage1 / 13
    (1)Excellent
    Ghent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Mountain Views
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Grill
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 August 2013
    This was the perfect location for a base camp from which to explore the Hudson River Valley area. We took in a Tanglewood concert (40-minute drive) and explored the backroads...
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    About this property
    Enjoy a newly renovated and furnished, one bedroom guest cottage, in an enchanting and quiet area. Located behind a stone castle on a 2 1/2 acre park-like property it's a beautiful place to vacation. You also have access to a large 6 person hot tub and all the deck areas. The bedroom and living...
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    Location Information
    12075, Ghent, New York
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Stockbridge, MA
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Garden
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Location Information
    01262, Stockbridge, Berkshires
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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