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Vacation Rentals in Old Chatham, NY and nearby

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    1 / 5
    5 of 5 stars (1) Excellent
    Old Chatham
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 5
    5 of 5 stars (1) Excellent
    Old Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    The following rentals are within 25 kilometres of Old Chatham, New York.

    1 / 16
    5 of 5 stars (1) Excellent
    Hancock, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 20
    5 of 5 stars (6) Excellent
    West Stockbridge, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Mountain Views
    • Wi-Fi
    • Balcony
    • Patio
    • Grill
    • Washer
    • Porch
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    5 of 5 stars Reviewed 4 weeks ago
    We had a wonderful stay in this large, lovely house that contained everything we needed for comfort and convenience. We were impressed with the degree to which details were...
    5 of 5 stars Reviewed 2 November 2014
    Had an outstanding couple of weeks staying here; place was quiet, peaceful and not too far from civilization. All the amenities and space you could wish for and Cassandra and her...
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    1 / 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 / 4
    4 of 5 stars (1) Very good
    Hancock, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Satellite TV
    • Mountain Views
    • Internet Access
    • DVD Player
    • Washer
    • Air Conditioning
    • Parking
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Cozy ranch home 3 miles away from Jiminy Peak Ski Resort. Near MASS MOCA, Clark Art Institute, Williams College Contemperary Museum of Art, Williamstown Theatre Festival, Tanglewood, shopping, golf courses. Wrap around deck with beautiful mountain views. Family room with full wet bar & flat screen... View all property information
    Location Information
    Hancock, Berkshires
    4 of 5 stars Reviewed 11 August 2013
    Aside from the excessive amount of men's shirts in the closets (closets and drawers had not been emptied so storage space was minimal), the full trash bins and dirty dishes...
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    1 / 16
    4.5 of 5 stars (2) Very good
    Hancock, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Central Heating
    • Hot Tub
    • Internet Access
    • Shared Indoor Pool
    • DVD Player
    • Sauna
    • Satellite TV
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    A fully furnished and nicely appointed 2br/2ba suite. There's a full kitchen, living room with sofa sleeper, king bed in master bedroom, 2nd bedroom has either a king bed or two queen size beds(varies), washer/dryer, private balcony with mountain or valley views. Everything you need on your... View all property information
    Location Information
    Hancock, Berkshires
    5 of 5 stars Reviewed 5 September 2015
    Great location near all outdoor activities including hiking, biking, golf and water sports. Rooms were spacious with 3 TVs. Wi-Fi was fast. One of the poops was heated. Owner...
    4 of 5 stars Reviewed 25 October 2014
    Lovely place with pool, spa, gym, and movie theater. Units are a bit noisy between floors but otherwise nice and quiet. We had the unfortunate experience of having three small...
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    1 / 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 / 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
    • Parking
    • Washer
    Suitability
    • 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 / 26
    Hancock, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Washer
    • Mountain Views
    • Patio
    • Grill
    • Satellite TV
    • Air Conditioning
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Let this quaint 2-bedroom, 2-bathroom Hancock condo, which sleeps 6, be the perfect destination for your New England escape! This excellent property carries an abundance of amenities to make your northeast vacation one you’ll always cherish. Nestled along the scenic border of New York and... View all property information
    Location Information
    Hancock, Berkshires
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    1 / 16
    Columbiaville
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • DVD Player
    • Grill
    • Balcony
    • Porch
    • Patio
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Complete renovation with privacy. This rural mill worker's cottage has been upgraded with midcentury touches while leaving antique finishes. Overlooking the Kinderhook Creek rapids on a private paved road. Minutes to Hudson and Kinderhook, NY. This 1400 sf home is on three levels with laundry in... View all property information
    Location Information
    Columbiaville, New York
    1 / 19
    5 of 5 stars (1) Excellent
    Hancock, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Sauna
    • Hot Tub
    • Washer
    • Terrace
    • Shared Indoor Pool
    • Mountain Views
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Ski-In/Ski-Out Plus Year-Round Mountainside Fun. Wyndham Bentley Brook is situated right at the base of Jiminy Peak ski mountain, making this resort an exceptional choice for mountainside play. In winter, ski out your door and onto the lifts; in spring, summer and fall, enjoy hiking and horseback... View all property information
    Location Information
    Hancock, Berkshires
    5 of 5 stars Reviewed 9 September 2015
    The units are clean and spacious and well stocked. Movie theater, swimming pools, outdoor picnic area with grills. and the mountain adjacent has plenty of outdoor activities...
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    1 / 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 / 29
    Lenox, MA
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    • Wi-Fi
    • Private Garden
    • Patio
    • Parking
    • Air Conditioning
    • Satellite TV
    • Grill
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    AS YOU OPEN THE GATE FROM THE DRIVE YOU WALK ONTO YR FRONT DECK LEADING TO THE ENTRY , MUD ROOM WHICH HOLDS YR SUMMER NEEDS, SKIS AND BOOTS. THIS LEADS TO THE COTTAGE APT. [attached to the owner`s quarters} LIVING RM- HAS A SOFA SLEEPER TO ACCOMMODATE 2 MORE GUESTS. KITCHENETTE W/ LG CEILING... View all property information
    Location Information
    Lenox, 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
    1 / 16
    5 of 5 stars (2) Excellent
    Hancock, MA
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    • Mountain Views
    • Washer
    • Internet Access
    • Patio
    • Satellite TV
    • Grill
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Low long term rates. Call $2500/mo for 3 months. Free Electric Vehicle Charging Station! (240V 40A no J1772) Thanksgiving Special - Nov 24 - Dec 1 - $500 Christmas Special - Dec 20 - Dec 27 - $800 Ski Season Dec 1 - Mar 31 $8000 April $50/nt Summer Cultural May 26, 2014 - Seot 2, 2014 $7500 Summer... View all property information
    Location Information
    Hancock, Berkshires
    5 of 5 stars Reviewed 30 July 2015
    This is a lovely rental in the heart of the Berkshires. Each morning you wake up to a view of Jiminy Peak and the sounds of bird life. Tom and Susan are wonderful innkeepers and...
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    1 / 8
    Lenox, MA
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Parking
    • Internet Access
    • Private Garden
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    1 / 18
    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
    • Child-friendly
    • Smoking allowed
    • 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
    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
    Suitability
    • 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 / 25
    4.5 of 5 stars (3) Very good
    Valatie
    3 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    • Porch
    • Satellite TV
    • Patio
    • Internet Access
    • DVD Player
    • Grill
    • Air Conditioning
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Stunning New Lakefront Home Near Berkshires with Gourmet Kitchen, large expansive views of Kinderhook Lake. All the bells and whistles including a TV in the Master Bathroom and a whole house stereo system. This home is an air conditioned, upscale Craftsman- styled cottage with 75 feet of lakefront... View all property information
    Location Information
    Valatie, New York
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    1 / 13
    5 of 5 stars (2) Excellent
    West Coxsackie
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Housekeeping...
    • Balcony
    • Terrace
    • Grill
    • Patio
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Historic stone farmhouse set on 400 acres of peace and tranquility. Shared bath. The charming rooms have double (twin) beds, dresser, chair, windows overlooking the pond. Our guests have full use of the large farmhouse. Perfect setting for relaxing, hiking, biking, touring. River towns short... View all property information
    Location Information
    West Coxsackie, New York
    5 of 5 stars Reviewed 10 November 2015
    Very clean, spacious rooms, and modern bathrooms in a old historic farmhouse. The harvest table in the kitchen is comfortable for a crowd. Great living room and fireplace. There...
    5 of 5 stars Reviewed 9 November 2015
    Loved the animals, the fresh produce, the fireplace, and the hosts! And lets not forget Bobo and Miss Michigan! It was a perfect setting for getting together with friends and...
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    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 / 21
    5 of 5 stars (22) Excellent
    Lenox, MA
    4 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    • Porch
    • Washer
    • Parking
    • Internet Access
    • Central Heating
    • Grill
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Located on a quiet side street in the charming Berkshire town of Lenox, Gartner House is a great place to call home while exploring this scenic, historical, and culturally rich area of Western Massachusetts. Walk to breakfast, lunch or dinner at one of the town's many charming restaurants, explore... View all property information
    Location Information
    Lenox, Berkshires
    5 of 5 stars Reviewed 20 January 2016
    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 16 October 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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    1 / 14
    Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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
    Location Information
    Chatham, New York
    1 / 24
    5 of 5 stars (6) Excellent
    Stephentown
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Parking
    • Mountain Views
    • Wi-Fi
    • Grill
    • DVD Player
    • Outdoor Dining Area
    • Balcony
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Countryside setting with a fantastic view of the Berkshires and centrally located. 10 minutes to Jiminy Peak ski area, 30 minutes to Tanglewood, 25 minutes to Stockbridge, 20 minutes to Mt. Greylock, 25 minutes to Williamstown theater. the lodge has a 400 square foot grand room for parties,... View all property information
    Location Information
    Stephentown, New York
    5 of 5 stars Reviewed 1 week ago
    My siblings and I (8 adults total) spent a wonderful weekend at the Blueberry Lodge. Most of our time was spent at the lodge except for an afternoon and evening attending the...
    5 of 5 stars Reviewed 8 March 2016
    My girlfriends and I have been going on yearly ski trips primarily in NH, VT, and ME for the past 29 years. This year we decided to try the Berkshires, for some place different...
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    1 / 10
    4.5 of 5 stars (6) Very good
    Richmond, MA
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Parking
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    • Air Conditioning
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    • Satellite TV
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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 / 13
    Hancock, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
    • Washer
    • Air Conditioning
    • DVD Player
    • Mountain Views
    • Grill
    • Sauna
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Luxury Condo in Beaver Pond, Hancock, Mass. Three bedrooms, loft, 2 baths, living room, kitchen with dining area, deck w/grill. Near Clark Art Museum, MassMoca. Williams College with schedule of sports open to the public: swimming, tennis, squash, basketball, skating and fitness room. Indoor... View all property information
    Location Information
    Hancock, Berkshires
    1 / 25
    Coxsackie
    6 Bedrooms, 3 Bathrooms, Sleeps 25 | Quick View
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    • Satellite TV
    • Waterfront
    • Patio
    • Air Conditioning
    • Grill
    • Washer
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The Hudson Hideaway is an inviting 6 Bedroom home with its own private beach in a quiet residential neighborhood. Sun yourself on our private dock or take a dip in the Hudson River to cool off. Relax at night on the back patio overlooking the river while a cozy fire blazes in the new outdoor brick... View all property information
    Location Information
    Coxsackie, New York
    1 / 20
    Richmond, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Porch
    • Internet Access
    • Washer
    • Air Conditioning
    • Satellite TV
    • Shared Outdoor Pool...
    • Grill
    • Patio
    Suitability
    • 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
    Location Information
    Richmond, Berkshires
    1 / 22
    Lenox, MA
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    • Internet Access
    • Satellite TV
    • DVD Player
    • Grill
    • Air Conditioning
    • Mountain Views
    • Washer
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    1 / 14
    4.5 of 5 stars (3) Very good
    Hancock, MA
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
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    About this property
    Come and enjoy our beautiful mountain retreat - A home for every season. This charming home away from home is a wonderful place for family, friends and romance. Only 3 minutes from Jiminy Peak! With over 2200 square feet, this new country home has plenty of space for everyone yet a very cozy... View all property information
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    Hancock, Berkshires
    1 / 6
    Hancock, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Two Bedroom Ski Condo at base of Jiminy Peak. Renovated kitchen, fireplace, deck and a large livingroom with vaulted ceilings. Rent from the owner and save. View all property information
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    Hancock, Berkshires
    1 / 14
    Hancock, MA
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    Commanding a stunning view of the Jiminy Peak ski area, Vacation Village in the Berkshires offers endless recreational activities and many of the comforts of home. Lounge or swim in the indoor or outdoor pool. Go hiking, biking, fishing or horseback riding around the property or enjoy the off site... View all property information
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    Hancock, Berkshires
    1 / 14
    Hancock, MA
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    Whitman Woods offers privacy with proximity to excellent skiing at Jiminy Peak (less than 5 minutes away) and to many cultural attractions of the Berkshires including Williamstown Theater Festival and Tanglewood. For outdoor lovers, Whitman Woods is near Mount Greylock Reservation, Audubon's... View all property information
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    Hancock, Berkshires
    1 / 24
    Lenox, MA
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Sauna
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    • Shared Indoor Pool
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    220+ Acres W\ Tennis Cts, Indoor / Outdoor Pool, Canoe, Fishing Boat, Hot Tub. New first time rental of 4 BR, 2BA, Cape Cod style, sleeps 10-12. New fully equipped kitchen w/ center island, indoor and outdoor barbecues, wine cooler, 2 fireplaces, large deck with 8 person hot tub and super seating... View all property information
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    Lenox, Berkshires
    1 / 14
    Spencertown
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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 / 25
    5 of 5 stars (10) Excellent
    Hancock, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • Pet-friendly
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    • x
    About this property
    Secluded mountain home surrounded by 27 acres yet convenient to major attractions including Jiminy Peak, Williamstown, Hancock Shaker Village, Tanglewood, and MassMOCA. Home offers 3 bedrooms and 2 full baths with finished basement recreation room. Updated kitchen with all amenities needed for home... View all property information
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    Hancock, Berkshires
    5 of 5 stars Reviewed 23 August 2016
    Thanks Kevin for renting your place to us. We love it there!!! The place is nice and cozy for our family. Everything we needed was all there. My family have a great time there...
    5 of 5 stars Reviewed 22 June 2016
    This was a perfect weekend retreat for our extended family of six (three adult couples). The house is very warm and inviting, clean, and well-equipped. The surrounding woods and...
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    1 / 19
    Philmont
    3 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    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 / 14
    Hancock, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    ***AVAILABILITY SUBJECT TO CHANGE WITHOUT NOTICE. RATES ARE SUBJECT TO CHANGE UNTIL RESERVATION IS CONFIRMED*** Bentley Brook, located in the Jiminy Peak ski area, offers a variety of on-site amenities -- from downhill skiing to swimming and biking. The Berkshire area also provides a vast array of... View all property information
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    Hancock, Berkshires
    1 / 21
    4.5 of 5 stars (9) Very good
    Hancock, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Skiing: Property Is...
    • Air Conditioning
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    • x
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    Wyndham Bentley Brook Rental includes: King bed master, 2 doubles in the 2nd bedroom, queen sleep sofa, full living room, dining room and kitchen with utensils. New York + New Jersey Flock to Hancock Mass/Jiminy Peak Ski Area, rated Top 5 Family Mountains in the Northeast! Wyndham Bentley Brook... View all property information
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    Hancock, Berkshires
    5 of 5 stars Reviewed 23 March 2015
    This is such a great property. We had a one bedroom unit which was still sufficient for 2 adults and 3 teens. Gorgeous large double bedroom with full bath and murphy bed and...
    4 of 5 stars Reviewed 26 January 2015
    Always a great trip for Friends and family. Easy quick park and party. They have a movie theater activities for kids all day long indoor outdoor swimming pool hot cider coffee and...
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    1 / 14
    Hancock, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    Bentley Brook is a ski in/ski out resort located at the base of Jiminy Peak ski resort. On-site Amenities Include: Heated Indoor/Outdoor Pool (year round), 3 hot tubs, 'Get out & Play ' children's program, 3 tennis courts, game room, exercise equipment, sauna, theater with nightly movies.. At... View all property information
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    Hancock, Berkshires
    1 / 10
    5 of 5 stars (1) Excellent
    Richmond, MA
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • DVD Player
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    • Private Garden
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    • Pet-friendly
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    • x
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    • 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
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    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
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    • 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 / 7
    Stephentown
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Garden
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    • x
    • x
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    • x
    About this property
    Perfect weekend retreat or short term furnished rental close to all Berkshire, MA amenities and Jiminy Peak Mountain Resort, museums, theatre, restaurants, shopping and more! 20 Minutes to Williamstown, 25 to Pittsfield, 30 to Albany. Home is efficient, easily maintained in an adorable 1870's... View all property information
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    Stephentown, New York
    1 / 25
    Canaan
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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 / 4
    Stephentown
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Two story cape that can sleep up to 12 people on 50 acres. Fully equipped kitchen, laundry area and dining & living room that faces the Berkshire Mountains. Relaxingy deck with barbecue. Walking trails and swimming pond make it a perfect getaway place. Wifi, a/c tv Near all Berkshire attractions,... View all property information
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    Stephentown, New York
    1 / 13
    West Coxsackie
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • ?
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    • x
    About this property
    Double room in historic stone farmhouse set on 400 acres of peace and tranquility. Shared bath. The charming room has a double (twin) bed, dresser, chair, windows overlooking the pond. Our guests have full use of the large farmhouse. Perfect setting for relaxing, hiking, biking, touring. River... View all property information
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    West Coxsackie, New York
    1 / 14
    Lenox, MA
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    This summer cottage built in the 1950's has recently been completely renovated from stem to stern to bring it up to date with the most current design standards. It is a 2-bedroom, 1-bathroom space with a beautiful backyard for grilling. There is also an amazing dining room surrounded by windows... View all property information
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    Lenox, Berkshires
    1 / 12
    Stephentown
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This cozy cottage is perfect for a small group of friends or a family getaway in the beautiful Berkshires. We're on 120 acres of private woods but only 7 miles from Jiminy Peak. The main space features a cathedral ceiling in the open living/dining area, with a glass-front woodstove for chilly... View all property information
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    Stephentown, New York
    1 / 9
    Canaan
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Porch
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • 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