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Holiday Rentals and Villas in Austerlitz, NY and nearby

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    1 / 18
    Austerlitz
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    The following rentals are within 15 kilometres of Austerlitz, New York.

    1 / 20
    5 of 5 stars (6) Excellent
    West Stockbridge, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    1 / 16
    5 of 5 stars (5) Excellent
    Stockbridge, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    1 / 10
    West Stockbridge, MA
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Washer
    • Grill
    • Air Conditioning
    • Patio
    • Wi-Fi
    • DVD Player
    • Mountain Views
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    West Stockbridge, Berkshires
    1 / 26
    Stockbridge, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
    • Patio
    • Grill
    • Parking
    • Satellite TV
    • Air Conditioning
    • Washer
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Stockbridge, Berkshires
    1 / 20
    5 of 5 stars (25) Excellent
    West Stockbridge, MA
    5 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • Central Heating
    • Grill
    • Internet Access
    • Patio
    • Satellite TV
    • DVD Player
    • Mountain Views
    • Washer
    Suitability
    • 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
    Location Information
    West Stockbridge, Berkshires
    5 of 5 stars Reviewed 9 May 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 30 March 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 / 27
    3.5 of 5 stars (2) Average
    Great Barrington, MA
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Porch
    • Grill
    • Air Conditioning
    • Satellite TV
    • Mountain Views
    • DVD Player
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Shaker Hill is a quirky rambling farmhouse located less than 3 hours from NYC and Boston. Hidden away down a 400’ unpaved driveway on 30 acres of fields and forest in the heart of the Berkshires, Shaker Hill is totally private and surrounded by 30 acres of rolling fields, diverse wetlands,... View all property information
    Location Information
    Great Barrington, Berkshires
    3 of 5 stars Reviewed 11 September 2014
    This is a very large house, more than adequate in size for a group of ten people. It has a big yard and a spectacular view of the mountains, especially from an upstairs window...
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    1 / 21
    Stockbridge, MA
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Wi-Fi
    • Private Garden
    • Parking
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Our cottage is situated in a private lake community. Short walk to lake and private beach. Minutes from Tanglewood, Kripalu, Stockbridge town center and Lenox town center. Convenient to many cultural institutions, hiking, skiing. Our cottage has plenty of outdoor space for relaxing and dining.... View all property information
    Location Information
    Stockbridge, Berkshires
    1 / 52
    5 of 5 stars (8) Excellent
    North Egremont, MA
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Wi-Fi
    • Grill
    • Satellite TV
    • Waterfront
    • DVD Player
    • Patio
    • Air Conditioning
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    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
    Location Information
    North Egremont, Berkshires
    5 of 5 stars Reviewed 19 July 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 7 October 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 / 10
    5 of 5 stars (2) Excellent
    Great Barrington, MA
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Air Conditioning
    • Grill
    • Internet Access
    • Mountain Views
    • DVD Player
    • Washer
    • Porch
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Please note that this property is not winterized so it's not available this winter of 2012. I am winterizing this spring & the property will be available on a year around basis stating on 5/15/2013. Please go to VRBO.com listing #219964 to see my reviews, I am new to flipkey. Located in South... View all property information
    Location Information
    Great Barrington, Berkshires
    5 of 5 stars Reviewed 20 May 2013
    This was a perfect weekend for us. I am very picking when choosing a cabin rental because I want it to be "just right--" to fit into all of my ideal visions of the quintessential...
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    1 / 8
    5 of 5 stars (2) Excellent
    West Stockbridge, MA
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Internet Access
    • Air Conditioning
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    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 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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    1 / 32
    5 of 5 stars (2) 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
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Stockbridge, Berkshires
    5 of 5 stars Reviewed 3 December 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 18 July 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 / 11
    3.5 of 5 stars (4) Average
    Stockbridge, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Grill
    • Central Heating
    • Internet Access
    • Washer
    • Satellite TV
    • Mountain Views
    • Waterfront
    • DVD Player
    Suitability
    • 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
    Location Information
    Stockbridge, Berkshires
    4 of 5 stars Reviewed 21 July 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 14 July 2015
    Those who used the cottage this week ranged from me alone to one night with eight people for one night. Sleeping was not a problem. The house is ideally located between Lenox...
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    1 / 12
    5 of 5 stars (3) Excellent
    Alford, MA
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Hot Tub
    • Mountain Views
    • Satellite TV
    • Waterfront
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Housekeeping...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • 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
    1 / 26
    5 of 5 stars (8) Excellent
    Hillsdale
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Parking
    • Mountain Views
    • Central Heating
    • Washer
    • Grill
    • Satellite TV
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Hillsdale, New York
    5 of 5 stars Reviewed 2 July 2016
    Had a short trip with the family to attend a wedding in the berkshires. The house is beautifully decorated and perfectly equipped. It has surpassed our expectations and we just...
    5 of 5 stars Reviewed 21 December 2015
    Owners were delightful to deal with. House was clean and well equipped. Would definitely rent again for a ski weekend! Really enjoyed family dinner at "The Gypsy Joint" in nearby...
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    1 / 13
    5 of 5 stars (1) Excellent
    Ghent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Wi-Fi
    • Mountain Views
    • Satellite TV
    • Patio
    • DVD Player
    • Grill
    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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.<BR><BR>The bedroom and... View all property information
    Location Information
    Ghent, New York
    5 of 5 stars Reviewed 6 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 full...
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    1 / 25
    Stockbridge, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • Parking
    • Patio
    • Grill
    • Mountain Views
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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
    1 / 14
    Great Barrington, MA
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Wi-Fi
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    • Mountain Views
    • Private Garden
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    Location Information
    Great Barrington, Berkshires
    1 / 23
    5 of 5 stars (1) Excellent
    Stockbridge, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Air Conditioning
    • Hot Tub
    • Wi-Fi
    • Mountain Views
    • Waterfront
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Stockbridge, Berkshires
    1 / 19
    5 of 5 stars (1) Excellent
    Canaan
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Terrace
    • Grill
    • DVD Player
    • Parking
    • Central Heating
    • Mountain Views
    • Washer
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Mountain Top Custom Built Post + Beam Home Highest Point in Columbia County - Mercer Mountain 2500 Sq Ft Home with Incredible Views and Sunsets Large 1000 Sq Ft Deck - Privacy - 6.25 Acres Hand Cut Beams from Nova Scotia with Stone Throughout Ist Floor Master Suite - 2 Bedrooms on 2nd Floor - Loft... View all property information
    Location Information
    Canaan, New York
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    1 / 30
    Stockbridge, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Washer
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Elevate your Stockbridge experience by staying at this 3-bedroom, 1.5-bath vacation rental house, which sleeps 6. Nestled within the serene forests of the Berkshires, ‘The Redway House’ is the quintessential setting for your next Massachusetts retreat. Welcome to ‘The Redway House’! You’ll... View all property information
    Location Information
    Stockbridge, Berkshires
    1 / 22
    Stockbridge, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
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    • x
    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... View all property information
    Location Information
    Stockbridge, Berkshires
    1 / 19
    Ghent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Satellite TV
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Mountain Views
    • Air Conditioning
    • Washer
    • Patio
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Ghent, New York
    1 / 11
    5 of 5 stars (2) Excellent
    Hillsdale
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Washer
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    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Hillsdale, New York
    5 of 5 stars 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...
    5 of 5 stars Reviewed 27 September 2015
    Bill and Lynne, the proprietors were wonderful. Very accommodating and helpful. Although located on highway 23, there is very little road noise as the apartment is brand new...
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    1 / 12
    5 of 5 stars (21) Excellent
    Great Barrington, MA
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Parking
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    • Shared Outdoor Pool...
    • Grill
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    • Central Heating
    • Mountain Views
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • 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
    Location Information
    Great Barrington, Berkshires
    5 of 5 stars Reviewed 5 August 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 26 July 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 / 4
    Stockbridge, MA
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Private Garden
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    • Pet-friendly
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    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Stockbridge, Berkshires
    1 / 4
    Stockbridge, MA
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Pet-friendly
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    • x
    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... View all property information
    Location Information
    Stockbridge, Berkshires
    1 / 10
    4.5 of 5 stars (6) Very good
    Richmond, MA
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Fantastic spot for families and for those looking for a quiet getaway. Come have some summer fun, enjoy the autumn colors or play in the snow. This year round cottage is the perfect spot for those who enjoy outdoor activities. The house is on a private dead end road, has a wonderful lake view... View all property information
    Location Information
    Richmond, Berkshires
    3 of 5 stars Reviewed 26 October 2015
    Better directions to the house would have been helpful. For two nights my daughter and two granddaughters joined us and found the yard and swingset fun. The weather was quite...
    5 of 5 stars Reviewed 7 September 2015
    This house was very comfortable and quiet. We had everything that we needed in the house. The house was clean. The beds were comfortable and cozy. The neighborhood was also quiet...
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    1 / 4
    Stockbridge, MA
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Private Garden
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    • Pet-friendly
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    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Stockbridge, Berkshires
    1 / 6
    West Stockbridge, MA
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Mountain Views
    • Parking
    • Wi-Fi
    • Terrace
    • Central Heating
    • Outdoor Dining Area
    • Balcony
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • 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
    Location Information
    West Stockbridge, Berkshires
    1 / 14
    Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • ?
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    About this property
    Waterfront Antique Farmhouse in the Berkshires with a Barn Gameroom. Our home, a 175 year restored Waterfront antique, is beautifully situated, on a tiered landscape with stone steps and sweeping lawns that border the creek. There are many pocket swimming holes and kayaking, canoeing, and... View all property information
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    Chatham, New York
    1 / 17
    Stockbridge, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
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    Stockbridge, Berkshires
    1 / 19
    5 of 5 stars (1) Excellent
    North Egremont, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • Smoking allowed
    About this property
    Enjoy beautiful Prospect Lake while staying at our comfortable home. Full kitchen with almost anything you can think of. Farm table seats 8 and is perfect for family meal. Cozy living spaces with enough seating for all to gather. Sunny bright deck in private rear yard . Covered porch is perfect... View all property information
    Location Information
    North Egremont, Berkshires
    5 of 5 stars Reviewed 12 October 2015
    It's my first time booking through flipkey. Zoe, the hostess, helped me a lot during the process. She is warm, kind, and patient. Her email was in details and we checked in...
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    1 / 20
    Richmond, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Porch
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Newly furnished 3 bedroom (with AC) & 2 1/2 bath single family home with stunning deck and in ground pool nestled in the quiet countryside opposite a horse farm. Situated minutes from West Stockbridge convenience stores and restaurants. Property is on 2 quiet tree lined acres with an enclosed... View all property information
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    Richmond, Berkshires
    1 / 5
    5 of 5 stars (1) Excellent
    Old Chatham
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Beautiful suite in a gorgeous county home in the Berkshires. Private entrance and your own courtyard with garden views. Large comfortable bed with plenty of pillows and luxurious spa- style bathroom. Close to Tanglewood, Jacobs Pillow, Kripalu, Great Barrington, and Hudson. Hiking, biking, and... View all property information
    Location Information
    Old Chatham, New York
    5 of 5 stars Reviewed 1 week ago
    We cannot say enough about how wonderful the property and the Owner are. Modern and well appointed, this property is beyond expectations. Private and immaculate, much time and...
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    1 / 10
    4 of 5 stars (1) Very good
    Great Barrington, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Outdoor Dining Area
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Our home is located in Great Barrington, given the title of the #1 Best Small Town in America by Smithsonian Magazine. There are many great restaurants, shopping, the Mahaiwe theater, a cineplex, golf, natural foods Co-op, a State Forest, yoga studio, and more. There are about twelve (12!) hiking... View all property information
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    Great Barrington, Berkshires
    1 / 18
    5 of 5 stars (1) Excellent
    Hillsdale
    3 Bedrooms, 2 Bathrooms, Sleeps 13 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
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    Hillsdale, New York
    1 / 15
    Great Barrington, MA
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
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    • Smoking allowed
    • x
    About this property
    Secluded high on a mountainside and surrounded by thousands of acres of state park and conservation land, The Pod is a rustic early 1970's timber and glass octagon set on a concrete pedestal. Decks on four sides with forest or distant mountain views. One stream runs within 15 feet of the master... View all property information
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    Great Barrington, Berkshires
    1 / 14
    Spencertown
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This Frank Lloyd Wright-inspired retreat is the perfect country escape for city dwellers. Set on 30 private acres with trails for hiking and a lake, this professionally decorated home blends rustic charm with modernity. There are two bedrooms, one with a fireplace, two bathrooms, plus a sleeping... View all property information
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    Spencertown, New York
    1 / 19
    Philmont
    3 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • x
    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... View all property information
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    Philmont, New York
    1 / 22
    Great Barrington, MA
    4 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This immaculate home is the place for relaxing, entertaining and sharing great times with family and friends. The house sets over 4 beautifully wooded acres. We call it the "illision of seclusion," as it is very private and yet is 5 minutes from the town as well as lakes, hiking, movies, theater,... View all property information
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    Great Barrington, Berkshires
    1 / 35
    Hillsdale
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    • x
    • ?
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    • x
    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... View all property information
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    Hillsdale, New York
    1 / 23
    5 of 5 stars (1) Excellent
    Craryville
    2 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Mountain Views
    • Grill
    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    You won't see another property like this. This is no ordinary barn. As you step inside you are greeted by a custom made dining room table that comfortably sits 16-20 people! Sit back and watch the deer/turkey/pheasant go by your window. Experience full upscale luxury in a beautifully restored and... View all property information
    Location Information
    Craryville, New York
    5 of 5 stars Reviewed 4 weeks ago
    The pictures and description don't do this place justice! There are no details left undone - Joe, our host, has thought of everything. The home was beautiful and FULLY stocked. It...
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    1 / 10
    5 of 5 stars (1) Excellent
    Richmond, MA
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Beautiful two bedroom house sits just steps from Richmond Pond. Enjoy a day on the water swimming and fishing followed by an evening enjoying the symphony at Tanglewood (ten scenic minutes away). Yoga enthusiasts will love the proximity to Kripalu (again, ten minutes away). Leaf peepers and skiers... View all property information
    Location Information
    Richmond, Berkshires
    5 of 5 stars Reviewed 14 June 2016
    My wife and I stayed here for a week in June. The hosts/owners are new to the rental business, but were eager to make sure everything was in order for us. The house is very well...
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    1 / 48
    Chatham
    4 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
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    Chatham, New York
    1 / 5
    5 of 5 stars (1) Excellent
    Old Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    'One of a kind' listing.<BR>Gated , 4BR Elegant Colonial Estate on Pristine River/stream in most desirable area in Columbia County.<BR>Set in sleepy upscale Historic Hamlet on Park-like grounds.<BR>Bordered by over 150 acres of fields with Sunset views.<BR>The best Swimming , fantastic Fishing,... View all property information
    Location Information
    Old Chatham, New York
    5 of 5 stars 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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    1 / 25
    Canaan
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    The Grey House is a relaxing retreat nestled on 7 acres of private, park-like setting. Close to lakes, hikes, cultural activities and skiing. This beautifully furnished property is perfect for accommodating large groups/families, and can sleep 6+. The Space This designer-decorated house with 3... View all property information
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    Canaan, New York
    1 / 25
    Great Barrington, MA
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • Internet Access
    • Mountain Views
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This home is uniquely and magnificently furnished by a retired couple that spent 18 years traveling and living abroad. Even local real estate agents have called the house “special”. It has 7,000 sf of living space (3 floors) with plenty of places to be together or to be alone (as one so chooses).... View all property information
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    Great Barrington, Berkshires
    1 / 9
    Canaan
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • 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
    1 / 9
    Stockbridge, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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