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Vacation Rentals in Colebrook, CT and nearby

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    The following rentals are within 20 miles of Colebrook, Connecticut.

    1 / 15
    5 of 5 stars (2) Excellent
    Sandisfield, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    1 / 27
    3.5 of 5 stars (2) Average
    Great Barrington, MA
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Otis, MA
    6 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    Tyringham, MA
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Balcony
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    • Mountain Views
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    About this property
    Charming, One Bedroom Cottage, former sculpting studio on the Santarella Estate in Tyringham, MA. Known as the 'Silo Studio', there is a bedroom with queen bed upstairs, sitting room, wet bar with Micro/Fridge and bath downstairs. Fall asleep to sounds of babbling brook and views to pond and forest... View all property information
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    Tyringham, Berkshires 01264
    Tyringham, MA
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Santarella Estate and Gardens in Tyringham, MA is a magical destination in the heart of one of the Berkshires' most beautiful valleys, located 3 miles from Interstate 90 and 15 minutes from most of the principal attractions (Tanglewood, Jacob's Pillow, Norman Rockwell museum, etc.) Pictures are... View all property information
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    Tyringham, Berkshires 01264
    1 / 11
    4 of 5 stars (1) Very good
    Great Barrington, MA
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Welcome to our School House Cottage located in the heart of the Berkshires. Set in front of the ledges of Warner Mountain, this historic home was originally a three room schoolhouse. An addition in the 1960's transformed it into a private home which it remained for many years. Now updated, the... View all property information
    Location Information
    Great Barrington, Berkshires 01237
    4 of 5 stars Reviewed September 10, 2015
    I spent a delightful month at the Schoolhouse cottage. It's comfortably furnished, and while I was by myself most of the time it didn't feel crowded when friends or family stopped...
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    1 / 14
    5 of 5 stars (1) Excellent
    Sheffield, MA
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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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... View all property information
    Location Information
    Sheffield, Berkshires 01257
    5 of 5 stars 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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    Great Barrington, MA
    4 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    About this property
    This immaculate home is the place for relaxing, entertaining and sharing great times with family and friends. The house sets over 4 beautifully wooded acres. We call it the 'illision of seclusion,' as it is very private and yet is 5 minutes from the town as well as lakes, hiking, movies, theater,... View all property information
    Location Information
    Great Barrington, Berkshires 01236
    1 / 10
    5 of 5 stars (2) Excellent
    Sheffield, MA
    3 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Charmingly restored 1840 cottage in the apple orchard of a working organic farm. Completely renovated in 2015 with thoughtful amenities, fresh eggs and produce and acres of trails and views. Close to waterfalls and lakes. Nearby ski hills, Tanglewood concerts, theatre, film festival, dance and... View all property information
    Location Information
    Sheffield, Berkshires 01257
    5 of 5 stars Reviewed July 24, 2015
    New England working farm. Lovely setting Great hospitality. Easy access to Tanglewood and other Berkshire attractions.
    5 of 5 stars Reviewed July 22, 2015
    What a beautifully decorated and comfortable cottage! Incredible deck for long lazy summer afternoons. Property owners were wonderful ... friendly & helpful. Cannot wait to...
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    1 / 10
    5 of 5 stars (2) Excellent
    Great Barrington, MA
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    About this property
    Please note that this property is not winterized so it's not available this winter of 2012. I am winterizing this spring & the property will be available on a year around basis stating on 5/15/2013. Please go to VRBO.com listing #219964 to see my reviews, I am new to flipkey. Located in South... View all property information
    Location Information
    Great Barrington, Berkshires 33304
    5 of 5 stars Reviewed May 20, 2013
    This was a perfect weekend for us. I am very picking when choosing a cabin rental because I want it to be "just right--" to fit into all of my ideal visions of the quintessential...
    5 of 5 stars Reviewed May 18, 2012
    This cabin was shared by re-uning nearby Berkshire School graduates and was perfect. It had all the needed amenities, WiFi, Hdtv with a dish, beautiful fireplace, nice kitchen...
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    Great Barrington, MA
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    About this property
    This home is uniquely and magnificently furnished by a retired couple that spent 18 years traveling and living abroad. Even local real estate agents have called the house “special”. It has 7,000 sf of living space (3 floors) with plenty of places to be together or to be alone (as one so chooses).... View all property information
    Location Information
    Great Barrington, Berkshires 01230
    1 / 23
    4.5 of 5 stars (2) Very good
    West Cornwall
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Furnished cottage, with large deck, on 4 acres of woods, with brook and 200 feet Housatonic River frontage. Use of Sharon beach, tennis courts, and children's play area. Located in the beautiful Litchfield Hills, the cottage is 2 minutes from West Cornwall and its covered bridge,10 minutes from... View all property information
    Location Information
    West Cornwall, Connecticut 06796
    5 of 5 stars Reviewed August 18, 2015
    Really enjoyed staying here with y sister and partner and my family (three young kids), who played endlessly in the stream which was full of frogs and stones. We could relax from...
    4 of 5 stars Reviewed January 30, 2015
    This was a wonderful cabin, no bells or whistles, but all of the amenities. It was comfortable clean and very spacious. The floor plan lends itself to lots of nooks and crannies...
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    1 / 31
    5 of 5 stars (1) Excellent
    Simsbury
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Near SKI SUNDOWN ~ New Nantucket Style Home ~ Spacious NEW 4 Bedroom, home, French Doors Galore! Light Bright & Open! Large Gourmet Kitchen, Nice Deck for relaxing! Situated on 4+ private acres, in a park like setting. Master suite + 1st floor bedroom suite. Private yet convenient getaway!Our... View all property information
    Location Information
    Simsbury, Connecticut 06070
    5 of 5 stars Reviewed July 7, 2015
    My three friends and I (two couples) are from NYC and found this place in search of a July 4th weekend getaway. The house itself is gorgeous and very spacious (at least compared...
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    Monterey, MA
    5 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • Skiing: Property Is...
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    About this property
    This is a beautiful Berkshire, post and beam private house nestled in the woods just off the Appalachian trail. Set on one of the Berkshires most coveted roads close to fresh water swimming in Lake Garfield, boating, fishing, classical outdoor concerts at Tanglewood & Skiing are all close by. The... View all property information
    Location Information
    Monterey, Berkshires 01245
    Barkhamsted
    6 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
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    • Balcony
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    About this property
    Nestled on the banks of the Farmington River, Legends offers comfortable rooms in a lodge setting with river views, breakfast Thursday -Sunday, healthy afternoon snacks and a special homemade juice of the day. All rooms offer AC, private bath, TV and internet. Fly-fishing,hunting kayaking, hiking,... View all property information
    Location Information
    Barkhamsted, Connecticut 06063
    1 / 17
    4 of 5 stars (1) Very good
    Goshen
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Located in the heart of northwestern Connecticut's elegant Litchfield County. The house is a fully furnished, newly constructed 5 bedroom / 4 bathroom home complete with a beautiful kitchen, fireplace, deck, state-of-the-art home theater system and all the amenities of Woodridge Lake. You will... View all property information
    Location Information
    Goshen, Connecticut 06756
    4 of 5 stars Reviewed April 16, 2013
    Very nice house !!! The house had almost everything you would ever need. But it was a big mistake Not having any cable tv or Sat tv. I would stay again if it would just get basic...
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    1 / 42
    5 of 5 stars (3) Excellent
    Lakeville
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This newly renovated 4 bedroom, 3 bath house is fully furnished and available for short or long term rentals. This house has a new kitchen, air conditioning, cable TV and wireless internet. It is located approximately 200 feet from the entrance to the Town Grove which offers many recreational... View all property information
    Location Information
    Lakeville, Connecticut 06068
    5 of 5 stars Reviewed May 26, 2014
    My friends and I stayed at this house for a race weekend at Lime Rock Park. The location of this house is perfect - 15 minutes from the track, walking distance from a small lake...
    5 of 5 stars Reviewed May 6, 2014
    We rented this sweet home in Lakeville for the bride and bridesmaids for my son's wedding. The bridal party came from far and wide and this was the perfect destination for the...
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    1 / 11
    5 of 5 stars (15) Excellent
    Falls Village
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Rare property available for vacation rental in Falls Village Ct Originally dating to 1800 's this highly unique property was purchased in 1999 by artist and master craftsman Mario Genova. The interior features plaster throughout, stone, marble and terra cotta mosaic flooring and wonderful... View all property information
    Location Information
    Falls Village, Connecticut 06031
    5 of 5 stars Reviewed May 29, 2015
    My husband and I stayed here for a recent visit on a trip to New England. We chose this Falls Village cottage and it was truly wonderful. Everything from the location, right up...
    5 of 5 stars Reviewed April 9, 2015
    I have been traveling to the northwest of Connecticut since my teens, spending a lot of weekends at Lime Rock and Sharon where my daughters spent their summers in a camp. There...
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    Tyringham, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This turn of the century cottage is located on a 130 acre property, and is stocked with linens. Three and a half baths, three full bedrooms, kitchen, living room, dining room, screened porches, a deck, and washer dryer. The house is across the brook and up a stone staircase (30 steps) from the... View all property information
    Location Information
    Tyringham, Berkshires 01264
    1 / 12
    5 of 5 stars (1) Excellent
    Torrington
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Large apartment, windows on 3 sides, new appliances, Wi-Fi, Conveniently situated on Main street downtown Torrington, from one to ten minutes away from restaurants, ten minutes away from movies theater, ten minutes away from the Post office, and all this is walking time to these locations, one... View all property information
    Location Information
    Torrington, Connecticut 06790
    5 of 5 stars Reviewed August 14, 2015
    Stayed in this splendid apartment for 2 weeks in July- August 2015. Not only Denis was a great host. But he did install air conditioning in our bedroom, after I asked if there...
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    Great Barrington, MA
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Sweet cozy house with plenty of room for large groups coming to enjoy the treasures of the Berkshires. Nestled behind Monument Mountain in Great Barrington. 4 bedrooms, 2.5 bathrooms, a spacious kitchen, living room, TV room, & two cars garage. Located within a neighborhood friendly to children.... View all property information
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    Great Barrington, Berkshires 01230
    1 / 12
    5 of 5 stars (19) Excellent
    Great Barrington, MA
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    Berkshires: Romantic Berkshires Cottage with Stunning Views (Great Barrington) The Berkshires in spring, summer and fall are alive with beauty, and now is the time to plan your restoring getaway in this idyllic studio cottage with its glorious views of the rolling hills and verdant meadows..... View all property information
    Location Information
    Great Barrington, Berkshires 01230
    5 of 5 stars Reviewed October 25, 2015
    My husband and I stayed at this very charming cottage for 3 nights in the beginning of October and we very much enjoyed our stay. The furniture and decor were very french...
    5 of 5 stars Reviewed August 27, 2015
    I stayed in the cottage with my girlfriend and our small dog and we had a fantastic time! The cottage had everything we needed (wifi, large bathroom, dining table, cable TV) and...
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    South Lee, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Two Bedroom two bathroom condo located on beautiful resort in the Berkshires. Oak and Spruce Resort located 15 minutes to Tanglewood is the summer home in the Berkshires of the Boston Symphony Orchestra. Condominium sleeps 6 with an eat in kitchen and living area. Recreational activities, ample... View all property information
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    South Lee, Berkshires 01260
    Monterey, MA
    5 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Get away from it all at our beautiful Berkshire lakefront wooded retreat. Swim, canoe, kayak, sunbathe, play tennis during the day, then enjoy the evening a short drive away at Tanglewood, Jacobs Pillow, or perhaps go to the movies in Great Barrington. Have dinner at the Red Lion Inn, or one of the... View all property information
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    Monterey, Berkshires 01245
    Great Barrington, MA
    5 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Welcome to my dream come true! Pick from your own orchards, vegetable gardens and perennial beds. Swim in your own Green River or your beautiful heated swimming pool. And of course, SKI, SKI, SKI!! This home is beautiful four seasons of the year. Major highlights include a fireplace in the kitchen... View all property information
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    Great Barrington, Berkshires 01230
    1 / 23
    Great Barrington, MA
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    About this property
    This Elegant Luxury Estate offers 6000+ SF of Living Space on 13+ park-like, sunny acres located within only minutes from the downtown Great Barrington. This fantastic home offers 5 Bedrooms, 4.5 bathrooms, sweeping dual staircase ending with the magnificent open gallery, the kitchen offers the... View all property information
    Location Information
    Great Barrington, Berkshires 01230
    1 / 10
    4 of 5 stars (1) Very good
    Great Barrington, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Our home is located in Great Barrington, given the title of the #1 Best Small Town in America by Smithsonian Magazine. There are many great restaurants, shopping, the Mahaiwe theater, a cineplex, golf, natural foods Co-op, a State Forest, yoga studio, and more. There are about twelve (12!) hiking... View all property information
    Location Information
    Great Barrington, Berkshires 01230
    4 of 5 stars Reviewed February 2, 2015
    My cousin and I thoroughly enjoyed our stay. The house was cozy and very convenient for our needs. Having a laundry room just off the kitchen was great when we came back from the...
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    Great Barrington, MA
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Charming get-a-way in a friendly residential neighborhood in Great Barrington. Our home is sunny and bright, with an eat-in-kitchen, casual living room and dining area with beautiful picture windows, three comfortable bedrooms, and 1.5 bathrooms. Fully furnished with an eclectic mix of modern and... View all property information
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    Great Barrington, Berkshires 01230
    South Lee, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    About this property
    Close to ski resorts, cross country skiing, restaurants, and all the cultural offerings of the Berkshires. The Berkshire region is a year-round destination for vacationers, so the Oak N’ Spruce Resort offers guests a selection of amenities to keep them coming back no matter what season. The... View all property information
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    South Lee, Berkshires 01260
    Tyringham, MA
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Balcony
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    • x
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    About this property
    A bright, lovely and comfortable room with queen bed in a charming country farmhouse with adjoining private bath. Located in Tyringham, a bucolic, rural village on a scenic country road the beautiful and magical 'Hop Brook' valley. The house is surrounded by farmland surrounding it on all sides. A... View all property information
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    Tyringham, Berkshires 01264
    Cornwall Bridge
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Mountain Views
    • DVD Player
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    • Private Indoor Pool
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    • Sauna
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    • ?
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    Prana Residence-Spa creates an environment for relaxation and the rejuvenation of vital life (prana). If you appreciate tranquility in the pursuit of personal happiness and are inspired by unique surroundings, personal spa facilities and select services, Prana Residence-Spa is waiting for you.... View all property information
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    Cornwall Bridge, Connecticut 06754
    Monterey, MA
    Studio, 2 Bathrooms, Sleeps 7 | Quick View
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    You'll love our hand-hewn post & beam beauty on 13 acres in the Berkshire Mountains of Western Mass located near the Monterey/Great Barrington line, close to everything. Great for summer and winter ski season. Rich in both outdoor and cultural attractions, shopping and antiquing. Located adjacent... View all property information
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    Monterey, Berkshires 01245
    Tyringham, MA
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
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    • Central Heating
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    • Porch
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    About this property
    Located on the Santarella Estate, an historic site located in the the Massachussetts' Berkshires. The colonial home is the former residence of sculptor Sir Henry Hudson Kitson. The estate includes the landmark, iconic storybook style 'Gingerbread House,' designed by Kitson to look like an English... View all property information
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    Tyringham, Berkshires 01264
    1 / 24
    Barkhamsted
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Waterfront
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    This turn-of-the-century, family. year round lake lodge is in the township of Barkhamsted, Connecticut. It is in the foothills of the Berkshires, nestled at the northwest bank of Connecticut's clearest lake, West Hill Lake. The owner retained the nostalgic feel of a comfortable antique lake home... View all property information
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    Barkhamsted, Connecticut 06063
    1 / 13
    4.5 of 5 stars (16) Very good
    Monterey, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Satellite TV
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    • Hot Tub
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    About this property
    Charming house with the feeling of a cottage, set on a knoll with adjacent cathedral-like pine forest. ** Stone fireplace, woodstove, beautiful kitchen with modern appliances (gas stove, microwave, refrigerator with water/ice dispenser, dishwasher, breadmaker, crockpot, blender, etc.) **... View all property information
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    Monterey, Berkshires 01245 0933
    5 of 5 stars Reviewed November 18, 2015
    I took my wife and three young children up to this house for columbus day week. We had a blast. The house has a real cabin in the woods feel and is just a short walk to the...
    4 of 5 stars Reviewed November 9, 2015
    When looking for a house to rent in the Berkshires I began with spots in the towns. However we chose this place due to the reasonable price. As it turned out we liked the remote...
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    1 of 5 stars (1) Terrible
    Great Barrington, MA
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Washer
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    • Pet-friendly
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    • ?
    • ?
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    Located in a wooded area overlooking a pristine lake, this woodsy style contemporary is a sportsman's paradise. It's a short drive to skiing (Jiminy Peak, Butternut, Catamount) and cultural attractions, (Tanglewood, National Music Center, Aston Magna, etc.) or you can fish, swim, boat, hike, or... View all property information
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    Great Barrington, Berkshires 01236
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    5 of 5 stars (1) Excellent
    Salisbury
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Outdoor Dining Area
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    About this property
    For the price of a motel room, enjoy a cabin on a lake. Great casual summer-fall vacation place for a small family with room for guests. MINIMUM 14 DAY STAY. THOUGH DAILY AND WEEKLY RATES MUST BE SHOWN, WE DO NOT RENT FOR THESE SHORT PERIODS. SEE NOTE BELOW. Great room, master bedroom, and... View all property information
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    Salisbury, Connecticut 06079
    5 of 5 stars Reviewed September 7, 2014
    My wife and I and two small children stayed at the cabin for one month after a big road trip adventure across the country from California. It was exactly what we needed! Our pace...
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    Great Barrington, MA
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Private Yard
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    • x
    About this property
    One bedroom, one bathroom cottage on beautiful country road. Private garden and screened-in porch. Two miles to shops and restaurants of downtown Great Barrington. Enjoy nearby skiing, cycling, fishing, hiking and golf. The Space: Quaint cottage with wood burning stove. Ideal base for enjoying... View all property information
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    Great Barrington, Berkshires 01230
    West Cornwall
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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    • Child-friendly
    • x
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    About this property
    Architect-designed, contemporary, 3-bedroom country home. Sited on five private hillside acres with breathtaking views of the Housatonic River Valley in the foothills of the Berkshire Mountains. With geothermal heating and air conditioning, heated floors, wood, slate, and stone flooring, gourmet... View all property information
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    West Cornwall, Connecticut 06796
    New Marlborough, MA
    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    Welcome to Mill River, and our 1905 Queen Anne style Victorian backing onto hundreds of acres of woods, deep in the heart of the Berkshires. Step in and enjoy the peace of sitting on the porch of an old house on a quiet country lane, the wind in the trees and the babble of the nearby stream. The... View all property information
    Location Information
    New Marlborough, Berkshires 01230