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Berkshires Luxury Vacation Rentals

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    Travellers to Berkshires are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    21 Matching Rentals in BerkshiresView all 146 rentals
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    Wyndham Bentley Brook Resort Rents-Hancock,MA -Jiminy Peak1 / 10
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Lake House1 / 18
    (4)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 9 Quick View
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    Country Elegance in the Berkshires1 / 22
    (2)Excellent
    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Balcony
    • Air Conditioning
    • Parking
    • Mountain Views
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located along the Appalachian trail and 3 miles to Great Barrington, this designer home is central to all the Berkshires has to offer, not to mention being 35 minutes to Hudson you are really in the center of of it all. This completely separate designer home is located on the 2nd and 3rd floors...
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    Sheffield, Berkshires 01257
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    4 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Outdoor Dining Area
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Washer
    • Patio
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lots of space, great yard, walk to everything: restaurants, museums, Williams College, theater, night life, etc. Plus, nearby ski and tubing areas. This beautifully maintained historic House On Main Street was known as the Victorian Tourist & Antique House in a by-gone era. It was originally...
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    Williamstown, Berkshires 01267
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 16
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Mountain Views
    • Air Conditioning
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THIS CUSTOM BUILT HOME is a one-of-a-kind, must see getaway retreat that is beautifully furnished, and meticulously maintained. The entire first floor 'guest suite' was designed to accommodate friends or extended family. The upper level is the main floor with an open plan kitchen, dining room, and...
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    9 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    • Grill
    • Patio
    • Wi-Fi
    • Washer
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is by far one of the nicest homes that you will come across in the area (or this site for that matter!). The estate comes complete with 7 bedroom, 7 bathroom main house, a guest house with 2 bedrooms and one bath, several fire places, a pool table, ping pong table, pool, jacuzzi, several TV's...
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    Great Barrington, Berkshires 01230
    Holiday Rental House - 9 Bedrooms, 8 Bathrooms, Sleeps 16
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Completely renovated vacation home with state of the art kitchen and marble baths, centrally located in the Berkshires 3 miles from Tanglewood, on 10 acres on a quiet country road. New in-ground pool surrounded by patio and expansive deck and pool house nestled in the woods. Central air...
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THIS IS A FULLY FURNISHED LARGE RETREAT IN THE HEART OF THE BERKSHIRES...SKIIING, LAKES, ANTIQUES, CRAFT SHOWS, ARTS, THEATRE ALL NEAR BY.....HOME IS IN A PRIVATE COMMUNITY WITH ITS OWN LAKE, POOLS, STATE OF THE ART FITNESS CENTER, CLUBHOUSE, HIKING TRAILS, TENNIS AND MORE! ONLY 2 1/2 HRS FROM NY...
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    Otis, Berkshires 01255
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Porch
    • Internet Access
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly furnished 3 bedroom (with AC) & 2 1/2 bath single family home with stunning deck and in ground pool nestled in the quiet countryside opposite a horse farm. Situated minutes from West Stockbridge convenience stores and restaurants. Property is on 2 quiet tree lined acres with an enclosed...
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    Richmond, Berkshires 01254
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Golden Triangle in the Berkshires1 / 4
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Mountain Views
    • Internet Access
    • DVD Player
    • Washer
    • Air Conditioning
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 11, 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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    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...
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    Hancock, Berkshires 01237
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Secure Parking
    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In 2016 Smithsonian Magazine deemed Great Barrington, 'The Best Small Town in America.' Manor Lane is a private French Country Estate located only 5 minutes from the heart of the Berkshires. Situated 10 minutes to both Butternut and Catamount ski mountains and 25 minutes to Tanglewood. Manor Lane...
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    Great Barrington, Berkshires 01230
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    BSO / Jacob's Tanglewood Ranch. Lenox-Stockbridge nexus. 5bdr/6bth. sleeps 24+1 / 72
    (2)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 30 Quick View
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    • Wi-Fi
    • Porch
    • Air Conditioning
    • Balcony
    • Washer
    • Mountain Views
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 27, 2017
    Excellent location to enjoy the best of the Berkshires, and a comfortable, spacious house full of historic character. 3 wood burning fireplaces and a screened porch make this...
    Reviewed May 29, 2016
    My family loved this house - parents and kids, all found it comfortable, spacious, and welcoming. Host is accommodative on last-minute changes or special requests. Easy...
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    About this property
    In the heart of the Berkshires: near Tanglewood, Jacob's Pillow, Jiminy Peak, Ski Butternut, Lenox MA, Stockbridge MA. Completely restored historic house with fully equipped kitchen, 5 bedrooms (each with a private bathroom), 3 spacious common rooms. A comfortable place for a family reunion,...
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    Lee, Berkshires 01238
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 30
    4 Bedrooms, 4 Bathrooms, Sleeps 15 Quick View
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    • Parking
    • Cable/satellite TV
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'We are located in the heart of America's cultural epicenter known as the Berkshires. Known as the ''Gatehouse'' to upscale Erskine Park, this truly one of a kind Craftsmen inspired home is filled with unique features and materials seldom found including eucalyptus and Brazilian Cherry flooring,...
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    Lee, Berkshires 01238
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 15
    The perfect Southern Berkshire winter vacation esc1 / 14
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 28, 2015
    Beautifully decorated house nestled in the Berkshires. A true getaway. Plenty of room for a family with the latest TV/computer set up. Big kitchen with the best appliances...
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    About this property
    This beautiful and secluded winter utopia is perfect for your Berkshire winter vacation getaway. Private and secluded, this home is nestled on five private acres in the woods located conveniently within fifteen minutes to many area attractions. Wether you are looking to ski the slopes, capture the...
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    Sheffield, Berkshires 01257
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    --Brand new 3400 sq ft Lee home in a private lake community, Berkshires --Situated on 4 wooded acres on a quiet country road --Pristine home features two master bedroom suites plus 3 additional bedrooms, 5 bathrooms --Spacious living room with vaulted ceiling & skylights --Fully equipped kitchen,...
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    Lee, Berkshires 01238
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This updated home has a luxurious feel! Close proximity to downtown Great Barrington is convenient and allows for easy access to the world's cultural epicenter. Located on a dirt road in a gentle neighborhood. About 1/2 mile from Lake Mansfield. Dehon road cuts over to the lake! The upgraded...
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    Great Barrington, Berkshires 01230
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    6 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Mountain Views
    • Cable/satellite TV
    • Grill
    • Washer
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The best vacation home in the Berkshires (ALL SEASONS): 9 private acres (far away from roads and neighbors), 6,800 ft² of living space, 6 bedrooms, sleeps 10 very comfortably. Ideal for 1, 2 or 3 families or those wonderful family reunions. There is a very large heated swimming pool. The pool is...
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    Great Barrington, Berkshires 01230
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 10
    6 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Secure Parking
    • Grill
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The best vacation home in the Berkshires: 9 private acres (far away from roads and neighbors), 6,800 ft² of living space, 6 bedrooms, sleeps 10 very comfortably. Ideal for 1, 2 or 3 families or those wonderful family reunions. There is a large heated swimming pool. The pool is completely...
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    Monterey, Berkshires 01245
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 10
    6 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Private Garden
    • Patio
    • Cable/satellite TV
    • Internet Access
    • Secure Parking
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The best vacation home in the Berkshires: 9 private acres (far away from roads and neighbors), 6,800 ft² of living space, 6 bedrooms, sleeps 10 very comfortably. Ideal for 1, 2 or 3 families or those wonderful family reunions. For winter it is 15 minutes from Butternut family ski area (ideal for...
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    Monterey, Berkshires 01245
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 10
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    7 Bedrooms, 8 Bathrooms, Sleeps 15 Quick View
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    • Wi-Fi
    • Parking
    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming former tavern and stage coach inn makes the perfect 4 season getaway for large group gatherings, family reunions, weddings or any occasion. Enjoy everything the Berkshires has to offer from the shops and restaurants in Great Barrington, skiing at Butternut Ski resort, and music and...
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    Great Barrington, Berkshires 01230
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 15
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