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Holiday Rentals and Homes in West Lebanon, NY

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    The following rentals are within 15 kilometers of West Lebanon, New York.

    1 / 16
    5 of 5 stars (1) Excellent
    Hancock, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Hancock, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 24
    5 of 5 stars (5) Excellent
    Stephentown
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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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
    • DVD Player
    • Air Conditioning
    • Washer
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • 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 01254
    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
    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 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 / 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 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...
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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 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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    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
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    1 / 16
    Nassau
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Patio
    • Grill
    • DVD Player
    • Air Conditioning
    • Washer
    • Satellite TV
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
    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 12184
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    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 01254
    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
    • 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 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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    Old Chatham
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Internet Access
    • Air Conditioning
    • Private Garden
    • Secure Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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 12136
    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
    • Child-friendly
    • Smoking allowed
    • 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
    Hancock, MA
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Terrace
    • Central Heating
    • DVD Player
    • Grill
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    Location Information
    Hancock, Berkshires 01237
    1 / 25
    5 of 5 stars (9) Excellent
    Hancock, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
    • Satellite TV
    • Outdoor Dining Area
    • Washer
    • Central Heating
    • Grill
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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 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...
    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...
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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
    • Child-friendly
    • x
    • Smoking allowed
    • 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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    Stephentown
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Mountain Views
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Outdoor Dining Area
    • Washer
    • Grill
    • DVD Player
    Suitability
    • 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
    Location Information
    Stephentown, New York 12168
    1 / 19
    5 of 5 stars (1) Excellent
    Canaan
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Terrace
    • Mountain Views
    • Grill
    • DVD Player
    • Central Heating
    • Balcony
    • Washer
    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 12060
    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 01237
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    Hancock, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
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    • Pet-friendly
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    • x
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    • x
    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
    Stephentown
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Parking
    • Washer
    • Mountain Views
    • Private Garden
    • Grill
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • 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
    Hancock, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • x
    About this property
    ***PRICE AND AVAILABILITY SUBJECT TO CHANGE WITHOUT NOTICE. PLEASE INQUIRE ABOUT DATES AND PRICE PRIOR TO SUBMITTING PAYMENT*** 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... 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
    • Child-friendly
    • x
    • Smoking allowed
    • 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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    Chatham
    4 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Patio
    • Terrace
    • Housekeeping...
    • Balcony
    • Central Heating
    • Washer
    • DVD Player
    Suitability
    • 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
    Location Information
    Chatham, New York 12037
    1 / 10
    5 of 5 stars (1) Excellent
    Richmond, MA
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • DVD Player
    • Washer
    • Private Garden
    • Satellite TV
    • Grill
    • Secure Parking
    • Patio
    Suitability
    • 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 01254
    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 / 5
    5 of 5 stars (1) Excellent
    Old Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • DVD Player
    • Grill
    • Waterfront
    • Patio
    • Satellite TV
    • Washer
    • Wi-Fi
    Suitability
    • 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 12136
    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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    Hancock, MA
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Washer
    • Sauna
    • Patio
    • Balcony
    • Mountain Views
    • Hot Tub
    • Terrace
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Stephentown
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
    • DVD Player
    • Balcony
    • Terrace
    • Satellite TV
    • Air Conditioning
    • Washer
    • Mountain Views
    Suitability
    • 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
    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
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    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
    • 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 12029
    New Lebanon
    5 Bedrooms, 5 Bathrooms, Sleeps 5 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This home sits on 10 private acres in the beautiful Berkshire mountains. Greeted by friendly wood carved bears, the entire estate consists of a 3 BR main house with 3.5 baths, two bedroom pool house with 1 bath, and 1 bedroom garage apartment with 1 bath. All units are available but this listings... View all property information
    Location Information
    New Lebanon, New York 12125