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Holiday Rentals and Homes in Old Chatham, NY

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    Old Chatham
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    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 kilometers of Old Chatham, New York.

    1 / 10
    4.5 of 5 stars (6) Very good
    Richmond, MA
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    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
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • 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
    Location Information
    Lenox, Berkshires 01240
    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
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • 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 01237
    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...
    5 of 5 stars Reviewed 16 October 2014
    This property is perfect for people with pets. Serene setting with a gorgeous view. The hosts, Tom and Susan, were gracious and very helpful. Highly recommended if your travels...
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    1 / 19
    5 of 5 stars (19) 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
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Quaint, , 2 story 1850's farmhouse in the Berkshires with original ceiling beams and 16' floor boards in much of the house. Fully furnished with 5 bedrooms, 2 full baths and a gorgeous screened-in porch overlooking 4 acres of gardens, stream and wooded mountains. Country kitchen with dish washer,... View all property information
    Location Information
    West Stockbridge, Berkshires 01266
    5 of 5 stars Reviewed 4 weeks ago
    Elaine was great! She may be the nicest person I have ever met. She was very accommodating, warm, and laid back; responsive to our needs, without ever being intrusive. House was...
    5 of 5 stars Reviewed 20 October 2015
    Elaine was a great hostess! We enjoyed her house immensely. It was fully equipped, clean and very comfortable. Very close to many quaint little towns. We look forward to a...
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    Lenox, MA
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Wi-Fi
    • Private Garden
    • Patio
    • Parking
    • Air Conditioning
    • Satellite TV
    • Grill
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    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- KITCHENETTE W/ LG CEILING FAN,TV, DVD & 2 CLOSETS. ENTER DRESSING RM, LG BATH... View all property information
    Location Information
    Lenox, Berkshires 01240
    Hancock, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
    • Sauna
    • Internet Access
    • Satellite TV
    • Shared Indoor Pool
    • Air Conditioning
    • Mountain Views
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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
    Location Information
    Hancock, Berkshires 01237
    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
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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 01237
    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 / 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
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Smoking allowed
    • Elder access
    • ?
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    About this property
    Cozy and modern two bedroom and one bath vacation home with lake nearby Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This luxury home can sleep up to 6 people and has lake access nearby. Enjoy a nice cup of hot chocolate by the fireplace in the living... View all property information
    Location Information
    West Stockbridge, Berkshires 01266
    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...
    5 of 5 stars Reviewed 26 November 2013
    Beautiful, modern and cosy home which proved to be a great base for the trip! The fire was an added treat at the end of the day! Location wise the cottage was perfect - close to...
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    Hancock, MA
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Washer
    • Sauna
    • Patio
    • Balcony
    • Mountain Views
    • Hot Tub
    • Terrace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • 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
    Location Information
    Hancock, Berkshires 01267
    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
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • 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 12075
    Austerlitz
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Washer
    • Parking
    • Shared Garden
    • Internet Access
    • Mountain Views
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This 3 Bedroom 2.5 bathroom recently constructed home sits on 40 wooded, secluded acres in Austerlitz, Columbia County, just 4 miles from the Massachusetts border. It offers stunning views of the Catskills, peace and quite and plenty of nature to watch from the back porch. Chatham, NY is 15 minutes... View all property information
    Location Information
    Austerlitz, New York 12017
    1 / 21
    5 of 5 stars (21) 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
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • 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 01240
    5 of 5 stars Reviewed 3 weeks ago
    My friends and I loved the Gartner home. It was conveniently located to downtown Lenox, cozily furnished and spotlessly clean. The eat in kitchen was well stocked with everything...
    4 of 5 stars Reviewed 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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    Hancock, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Private Indoor Pool
    • Sauna
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Discover an unparalleled vacation destination at Wyndham Bentley Brook. This premier Hancock, MA vacation resort is located at the foot of the ski slopes of Jiminy Peak Mountain Resort. After a full day of skiing, snowboarding, hiking and partaking in other seasonal activities, return to your... View all property information
    Location Information
    Hancock, Berkshires 01237
    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
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Architect-designed, one bedroom studio cottage in peaceful setting on quiet road with a 5 acre view! What more could you ask! Perfect haven for artist or writer or anyone wanting to get away! Only 15 minutes to Tanglewood or Kripalu This little gem has just been renovated, with built in couches,... View all property information
    Location Information
    West Stockbridge, Berkshires 12029
    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
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • 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. The bedroom and living... View all property information
    Location Information
    Ghent, New York 12075
    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 / 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
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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 01237
    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 / 14
    5 of 5 stars (5) Excellent
    West Stockbridge, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Mountain Views
    • Wi-Fi
    • Balcony
    • Patio
    • Grill
    • Washer
    • Porch
    • Central Heating
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located in West Stockbridge minutes from everything . Nestled in the Berkshire Mountains. Convenient yet Private. Visit our web-site aberkshirehome. The Berkshires is a world unto itself. It is scenic beauty married to cultural bounty. It is urban sophistication in an idyllic, rural setting. It is... View all property information
    Location Information
    West Stockbridge, Berkshires 01266
    5 of 5 stars Reviewed 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...
    5 of 5 stars Reviewed 25 August 2014
    We were excited to get away from NYC and stay in the Berkshires! It was a wonderful stay at this home! So spacious, comfortable, lots of thoughtful gestures for our stay! We...
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    Lenox, MA
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Parking
    • Internet Access
    • Private Garden
    • Air Conditioning
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Great little house in a very convenient location. Set nicely back from the street with a spacious back and side yard. 8 minutes drive to tanglewood. All rooms are furnished. Living room with bay window and fireplace, hardwood floors throughout. Almost an acre of land with large trees and garden.... View all property information
    Location Information
    Lenox, Berkshires 01240
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    West Stockbridge, MA
    5 Bedrooms, 2 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
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • 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 01266
    Hancock, MA
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • DVD Player
    • Central Heating
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    • Pet-friendly
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    • x
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    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
    Location Information
    Hancock, Berkshires 01237
    1 / 30
    Sand Lake
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Central Heating
    • Terrace
    • Grill
    • DVD Player
    • Balcony
    • Parking
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    This fully furnished 4 Bedroom house can easily sleeps 8 people and will accommodate both families and vacationers. In Sand lake a beautiful waterfront property in one of the most gorgeous places in Upstate New York. The water front property can come with a Tandem Kayak, Row Boat or a Canoe if... View all property information
    Location Information
    Sand Lake, New York 12153
    1 / 20
    Sand Lake
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
    • Internet Access
    • Porch
    • Parking
    • DVD Player
    • Waterfront
    • Washer
    • Central Heating
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This fully furnished 4 Bedroom house can easily sleeps 10 people and will accommodate both families and vacationers. In Sand lake a beautiful waterfront property in one of the most gorgeous places in Upstate New York. The water front property can come with a Tandem Kayak, Row Boat or a Canoe if... View all property information
    Location Information
    Sand Lake, New York 12153
    1 / 24
    5 of 5 stars (4) Excellent
    Stephentown
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Mountain Views
    • Parking
    • Grill
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • 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 500 square foot grand room for parties,... View all property information
    Location Information
    Stephentown, New York 12168
    5 of 5 stars Reviewed 21 November 2015
    I attended a group weekend workshop at the Berkshire Blueberry Lodge in Stephentown; foothills of the Berkshires. I cannot tell you how beautiful the lodge is; the breathtaking...
    5 of 5 stars Reviewed 13 September 2015
    We stayed in Blueberry Lodge with my fiance and family during Labor Day weekend. We loved the house which was comfortable and spacious enough for 8 of us. Breathtaking view from...
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    1 / 19
    5 of 5 stars (1) Excellent
    Hancock, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Sauna
    • Hot Tub
    • Washer
    • Terrace
    • Shared Indoor Pool
    • Mountain Views
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • 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 01237
    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 / 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
    • Grill
    • Satellite TV
    • DVD Player
    • Washer
    • Internet Access
    • Central Heating
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
    Location Information
    Hancock, Berkshires 001237
    5 of 5 stars Reviewed 7 October 2010
    We (family of 4) stayed a weekend in January 2010 with friends (family of 5). It is a great house, perfect location and the owner is really great to deal with. Highly recommended...
    4 of 5 stars Reviewed 7 October 2010
    My husband and I stayed here with our 2 teen age girls last summer. We looked for a house that was close to Jiminy Peake for a family gathering. The house was well equipped and...
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    Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • Child-friendly
    • ?
    • x
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    • Smoking allowed
    • Elder access
    • x
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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
    Location Information
    Chatham, New York 12184
    1 / 25
    5 of 5 stars (8) Excellent
    Hancock, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Mountain Views
    • Washer
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    • Central Heating
    • Outdoor Dining Area
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Elder access
    • 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
    Location Information
    Hancock, Berkshires 01237
    5 of 5 stars Reviewed 7 July 2015
    My eight year old daughter and I had a wonderful time staying in Hancock. We were joined at different times by young cousins and grandparents - the kids loved the inside (the bunk...
    5 of 5 stars Reviewed 12 October 2014
    Stayed here for a couple nights over labor day to get out of the city. The place is perfect for a group of 4 and even better for our 2 dogs. Great little creek for them to go...
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    1 / 12
    4 of 5 stars (1) Very good
    Lenox, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
    • Balcony
    • DVD Player
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    • Central Heating
    • Porch
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
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    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Charming, spacious and comfortable 1860's farmhouse adjacent to wildlife sanctuary. Cozy country decor with original wide plank floors, lovely views and outdoor dining or lounging on porch or deck. Walking distance to hiking trails in Pleasant Valley Wildlife Preserve or Kennedy Park. Quiet and... View all property information
    Location Information
    Lenox, Berkshires 01240
    4 of 5 stars Reviewed 8 July 2015
    Lovely farmhouse, convenient to Tanglewood and shops in Lenox as well as other nearby towns and sights. We were a family of 7, including a 2 year old, and the swing set in the...
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    1 / 16
    Nassau
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Patio
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Elder access
    • x
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    About this property
    Understated Post and Beam house on a private bluff with views of the Catskills. Elicits calm and pleasure on approach and entry. The house sits on 23 acres of open fields and wooded trails on a road (known locally for its beauty) with ponds and horse farm. The house has cathedral ceilings on both... View all property information
    Location Information
    Nassau, New York 12123
    Lenox, MA
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Sauna
    • Mountain Views
    • Hot Tub
    • Air Conditioning
    • Internet Access
    • Shared Indoor Pool
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    220+ Acres W\ Tennis Cts, Indoor / Outdoor Pool, Canoe, Fishing Boat, Hot Tub. New first time rental of 4 BR, 2BA, Cape Cod style, sleeps 10-12. New fully equipped kitchen w/ center island, indoor and outdoor barbecues, wine cooler, 2 fireplaces, large deck with 8 person hot tub and super seating... View all property information
    Location Information
    Lenox, Berkshires 01240
    Hancock, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • x
    • x
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    • x
    About this property
    ***Price and availability subject to change without notice*** 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 cultural and historic attractions. Visit... View all property information
    Location Information
    Hancock, Berkshires 01237
    Stephentown
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Satellite TV
    • Parking
    • Washer
    • Mountain Views
    • Private Garden
    • Grill
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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
    Location Information
    Stephentown, New York 12168
    Stephentown
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Mountain Views
    • Satellite TV
    • Internet Access
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    • Washer
    • Grill
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • 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
    Location Information
    Stephentown, New York 12168
    1 / 22
    Sand Lake
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Central Heating
    • Parking
    • Waterfront
    • Grill
    • Satellite TV
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    • Washer
    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
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    • x
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    About this property
    Welcome to 123 Lawson Rd. This 3 Bedroom 2 Bathroom home sits on a private pond at the end of a Dead End street. New kitchen with all black appliances and tile floor. The Dining Room has Hard wood floors and a Large living room with wood burning field-stone fireplace. Come see this one of a kind... View all property information
    Location Information
    Sand Lake, New York 12153
    Austerlitz
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    • Grill
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    • Pet-friendly
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    • Child-friendly
    • ?
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Newly built cabin in the woods. The cabin is perfect for a small family or couple. It is a perfect location for wanting to be close to the Berkshires, Hudson NY, and Copake Lake. Tons of hiking trails and swimming lakes for the summer and minutes from Butternut and Catamount ski resorts in the... View all property information
    Location Information
    Austerlitz, New York 12017
    Stephentown
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Wi-Fi
    • DVD Player
    • Balcony
    • Terrace
    • Satellite TV
    • Air Conditioning
    • Washer
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • 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
    Location Information
    Stephentown, New York 12168
    East Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Air Conditioning
    • Outdoor Dining Area
    • Wi-Fi
    • DVD Player
    • Patio
    • Mountain Views
    • Grill
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Our cottage has been lovingly maintained and is in pristine condition. It is also very well laid out. You will enter through a generous foyer with closet and antique breakfront, and pass the media room (optional 3rd bedroom) with a divided light glass wall separating it from the family room. The... View all property information
    Location Information
    East Chatham, New York 12060
    Hancock, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
    • DVD Player
    • Internet Access
    • Satellite TV
    • Mountain Views
    • Washer
    • Sauna
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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. Sledding on back terrace. Near Clark Art Museum, MassMoca. Williams College with schedule of sports open to the public: swimming, tennis, squash, basketball, skating and... View all property information
    Location Information
    Hancock, Berkshires 01237
    1 / 16
    4 of 5 stars (2) Very good
    Stephentown
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Grill
    • Parking
    • Satellite TV
    • Balcony
    • DVD Player
    • Internet Access
    • Terrace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Beautiful three bed room home with a private master bedroom with attached bath and deck. Two bedrooms downstairs with a shared bathroom. Modern Kitchen with everything you need to make wonderful meals, Large deck out the back with tables, chairs and gas grill. House has a spacious living room with... View all property information
    Location Information
    Stephentown, New York 12169
    4 of 5 stars Reviewed 29 October 2014
    Beautiful home, comfortable BUT there were no sheets on the bed. And when I contacted the owner nothing was done about it. Kitchen was outfitted with everything. There was a...
    4 of 5 stars Reviewed 27 July 2014
    We had a great time and would recommend this house to anyone looking for a quiet escape. The house was in great condition, with full kitchen, lots of room, carpeting, amazing...
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    1 / 18
    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
    • Satellite TV
    • Washer
    • Internet Access
    • Hot Tub
    • Sauna
    • Shared Indoor Pool
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    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
    Location Information
    Hancock, Berkshires 01237
    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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    Spencertown
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
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    • Patio
    • Satellite TV
    • Internet Access
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    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • 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
    Location Information
    Spencertown, New York 12165
    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
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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 12184
    5 of 5 stars Reviewed 18 February 2013
    The Doll house was such an exquisite stay! We had a couples retreat for Valentines day and the stay at this lake house was awesome from the moment we got here. The tub amazing...
    4 of 5 stars Reviewed 6 June 2012
    Yes, the house is wonderful. Beautiful views abound, it's well stocked with everything you'd want, and extremely clean. A five-star place. That said, the lake's dreadful, in our...
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    Valatie
    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Internet Access
    • Porch
    • Waterfront
    • DVD Player
    • Patio
    • Grill
    • Central Heating
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Homey A frame house filled with multiple items and family pictures collected over the years and during trips primarily to Africa and Asia. Directly on Kinderhook Lake in Town of Chatham, off private road with three other homes. Good for swimming and fishing. Halfway between Hudson with its... View all property information
    Location Information
    Valatie, New York 12184
    West Coxsackie
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Grill
    • Balcony
    • Terrace
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    • Housekeeping...
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • 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
    Location Information
    West Coxsackie, New York 12192
    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
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    A cute cabin in the woods with easy access to a lake a short 500 ft walk down a dirt road. Swimming is available at a private member beach by either canoe or a sort drive to the other end of the the Lake. Convenient to the Berkshires. Tanglewood is a 15 min drive and Jacob's Pillow and Saratoga... View all property information
    Location Information
    Canaan, New York 12029
    Lenox, MA
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Smoking allowed
    • Elder access
    • x
    About this property
    This summer cottage built in the 1950's has recently been completely renovated from stem to stern to bring it up to date with the most current design standards. It is a 2-bedroom, 1-bathroom space with a beautiful backyard for grilling. There is also an amazing dining room surrounded by windows... View all property information
    Location Information
    Lenox, Berkshires 01240
    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
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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 01254
    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
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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 12534