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Holiday Rentals in Winsted

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    All 29 Rentals in Winsted
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    Winsted
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    The following rentals are within 30 kilometers of Winsted.
    Berkshires House, 40 wooded acres, Lake Frontage1 / 48
    (20)Very good
    Monterey, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Quiet first floor apartment in Torrington1 / 12
    (6)Excellent
    Torrington
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    The Cottage at Great Falls1 / 18
    (19)Excellent
    Falls Village
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Mountain Views
    • Waterfront
    • Central Heating
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 November 2017
    Danielle responded to my vacation request in record time, and was very attentive before, during and after our stay. Everything was perfect when we arrived - the cottage was...
    Reviewed 14 September 2016
    Enjoyed our stay at this beautiful, well appointed cottage and would book again.Only issue is the lack of air conditioning which can be a problem if weather is hot and humid.
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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...
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    Falls Village, Connecticut 06031
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Windy Top Stone Cottage1 / 26
    (1)Excellent
    North Granby
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Secure Parking
    • Patio
    • Wi-Fi
    • Mountain Views
    • Air Conditioning
    • Grill
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 January 2018
    My wife and I arrived at Windy Top in the middle of a snowstorm. What a perfect place to be snowed in! The cottage was beautifully decorated for the season and our hosts, Ken...
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    About this property
    The Windy Top Cottage is an old stone building constructed in 1932 by H. L. Bitter, a wealthy Hartford businessman. This area of Granby was a favorite of the Hartford elite for a place to “summer” in the early part of the 20th Century. The cottage was the place where the domestic staff stayed when...
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    North Granby, Connecticut 06060
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Lake House1 / 13
    (1)Excellent
    Lakeville
    5 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Grill
    • Patio
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 February 2018
    Great place to getaway from it all. Owner was very helpful.Only draw back is there is a bit of Poison ivy and ticks but nothing to keep us away from going back.
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    About this property
    This is the lake cottage your grandmother visited during her childhood. Charming, original 1920 features. Big remodeled kitchen (new stove/oven) and big living room for family reunions and guests. Sleeps 9 in comfort; it has often slept 20. Porch overlooks Lake Wononscopomuc -- deepest lake in...
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    Lakeville, Connecticut 06039
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 9
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    Three-bedroom one-and-a-half bath ranch with lots of room inside and outside1 / 17
    (1)Excellent
    Granby
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Secure Parking
    • Patio
    • Air Conditioning
    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 April 2018
    This home was perfect for us! One-level living was key because my daughter was on crutches. Dianne takes great pride in keeping her home immaculate. Thank you Dianne!
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    About this property
    This large home has three bedrooms on one floor and there is a finished basement with new laundry machines and plenty of storage, as well as new fridge with icemaker and ceramic cooktop. Everything is clean and odor-free and there is a large bright open kitchen with sliders to a back deck and...
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    Granby, Connecticut 06035
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Riverwood - Cozy Carriage House in the Woods1 / 11
    (1)Excellent
    Falls Village
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Wi-Fi
    • Air Conditioning
    • Private Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 August 2018
    I would rate this higher than 5 stars. The location was perfect for our week. Close to family in the area, hiking, kayaking and motorcycling. The carriage house is immaculate...
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    About this property
    Lovely second-story guest house on wooded property. Generously sized bedroom with queen bed, comfortable bathroom with therapeutic river stone walk-in shower, petit fully equipped kitchen, and relaxing main room with leather dual-reclining loveseat, flat screen TV, private deck and dining area....
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    Falls Village, Connecticut 06031
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Apple Cottage1 / 10
    (4)Excellent
    Sheffield, MA
    3 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Wi-Fi
    • Mountain Views
    • Air Conditioning
    • Balcony
    • Parking
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 July 2016
    Our family of four (two adults and a 12 and 8 year old) recently stayed at Apple Cottage with my sister who lives in Boston and had a wonderful week. The house was perfect for...
    Reviewed 16 May 2016
    Tucked away down a country road, farm fresh eggs for breakfast, wonderful rustic cottage details everywhere, Apple Cottage does not disappoint! The cottage easily accommodated 7...
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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...
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    Sheffield, Berkshires 01257
    Holiday Rental House - 3 Bedrooms, 6 Bathrooms, Sleeps 8
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    Cornwall Bridge
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Mountain Views
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    • Internet Access
    • Private Indoor Pool
    • Air Conditioning
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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....
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    Cornwall Bridge, Connecticut 06754
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Monterey, MA
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Washer
    • Grill
    • Wi-Fi
    • Patio
    • Air Conditioning
    • DVD Player
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The lakeside house is built on a 1.1 acre lot with view of Lake Garfield. It is only three minute walk to the public beach with life guards on site. In the summer, Jacob’s Pillow Dance Center and Tanglewood Music Center are about 25 to 30 minutes away. In the winter, Ski Butternut resort is about...
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    Monterey, Berkshires 01245
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Charming 2+2 Lakeside Cottage on Best Lake in CT1 / 37
    (1)Excellent
    Salisbury
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Parking
    • Wi-Fi
    • Grill
    • Waterfront
    • Mountain Views
    • Outdoor Dining Area
    • DVD Player
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 September 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...
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    About this property
    For the price of a motel room, enjoy a cottage on a lake. Great casual summer-fall vacation place for a small family with room for guests. MINIMUM 14 NIGHT STAY. THOUGH DAILY AND WEEKLY RATES MUST BE SHOWN, WE DO NOT RENT FOR THESE SHORT PERIODS. MONTHLY RATE REQUIRES 32 NIGHT MINIMUM STAY....
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    Salisbury, Connecticut 06079
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    North Granby
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Loft at Lost Acres is a wonderfully private, rural getaway! This bright and comfortable space is located on the upper floor of the Lost Acres Vineyard service barn. Originally intended for the caretaker, the owners have decided to offer it to the public to enjoy the beauty of the vines & the...
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    North Granby, Connecticut 06060
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedroom Furnished House in Lakeville Connecticut1 / 42
    (3)Excellent
    Lakeville
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Porch
    • Washer
    • Cable/satellite TV
    • Outdoor Dining Area
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 May 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...
    Reviewed 6 May 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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    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...
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    Lakeville, Connecticut 06068
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Sheffield, MA
    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
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    The perfect Southern Berkshire winter vacation esc1 / 14
    (1)Excellent
    Sheffield, MA
    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 28 October 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
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    Renovated Barn1 / 15
    (1)Excellent
    Taconic
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Parking
    • Private Garden
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 July 2018
    Bebe (the owner) was extremely communicative from beginning to end. The house was even more beautiful in person. We will definitely be booking here again!
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    About this property
    Charming renovated Barn, very private, with pastoral views. Recently renovated throughout, the house features a double-height, vaulted ceiling in the Kitchen, Dining, and Living Rooms, with great light and views. Open deck off the Living Room overlooking a large, private meadow. Within a...
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    Taconic, Connecticut 06068
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Monterey, MA
    Studio, 2 Bathrooms, Sleeps 7 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Monterey, Berkshires 01245
    Holiday Rental House - 2 Bathrooms, Sleeps 7
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    Bloomfield
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Parking
    • Cable/satellite TV
    • Internet Access
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    BEAUTIFUL 100% NEWLY renovated Victorian Mansion, on 3.5 acre private ESTATE., directly alongside the ELEGANT greens and fairways of the prestigious private TUMBLE BROOK COUNTRY CLUB. LARGE INGROUND SWIMMING POOL. Great GOLF COURSE views from every window. PRIVATE- AWAY FROM THE ROADS- Large,...
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    Bloomfield, Connecticut 06002
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Monterey, MA
    5 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Waterfront
    • Mountain Views
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Monterey, Berkshires 01245
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 6
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    Otis, MA
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Grill
    • Washer
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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
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    Comfortable Rustic Cottage on 4 Wooded Acres with Brook1 / 22
    (3)Very good
    West Cornwall
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Porch
    • Parking
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Air Conditioning
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 August 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...
    Reviewed 30 January 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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    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. The brook will dry up during summer dry spells. Located in the beautiful Litchfield Hills, the cottage is 2 minutes from...
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    West Cornwall, Connecticut 06796
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    West Cornwall
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Mountain Views
    • Internet Access
    • Porch
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    West Cornwall, Connecticut 06796
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    East Otis, MA
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Balcony
    • Hot Tub
    • Parking
    • Wi-Fi
    • Grill
    • Terrace
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the beautiful Berkshires. Watch the horses roam. Have a guided trail ride (additional fee) or have a camp fire only feet away from the horses. Within steps from your accommodations, enjoy the largest recreational lake in Massachusetts. Bring your boat or jetski. Or use our row boat. Go...
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    East Otis, Berkshires 01029
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    New Marlborough, MA
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Balcony
    • Central Heating
    • Wi-Fi
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    • Washer
    • Terrace
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    New Marlborough, Berkshires 01230
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    Salisbury
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    East Twin Lakes, a charming three-bedroom lakefront cottage with private two docks, 200 feet of shore front with gorgeous views. The lake is clean and has the best fishing in Connecticut. Enjoy boating, water skiing, canoeing, sailing or fishing. The cottage is furnished and has a window air...
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    Salisbury, Connecticut 06068
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Colebrook
    3 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • DVD Player
    • Private Garden
    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to our tastefully decorated home in Colebrook - nestled in the woodlands, this two-acre retreat offers a tranquil escape for up to 6 people and is only a 5-minute drive from town. Curl up by the fire in the family room or grab a blanket and make some smores around the fire pit! Perfect for...
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    Colebrook, Connecticut 06021
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 12
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    New Marlborough, MA
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Washer
    • Central Heating
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The guest suite is within 'Keyes House,' a quintessential 19th century Greek Revival colonial. It is conveniently located in a small, bucolic village in Southern Berkshire County that is on the National Register of Historic Districts. The entire home, including the two-room suite, has been...
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    New Marlborough, Berkshires 01230
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Harwinton
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Weekly rental April through December, monthly rental offered January thu March. 2 bedroom, 1 bath, fireplace, with beautiful views of the lake Enjoy a classic New England vacation in this direct lake front home on Harwinton Lake. Relax and enjoy the pretty scenery and breezes in this quiet lake...
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    Location Information
    Harwinton, Connecticut 06791
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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