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Holiday Rentals in Winsted

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    Don't let other travellers get your favourite Winsted area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 26 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.
    Bloomfield
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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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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    Litchfield
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • Washer
    • Parking
    • DVD Player
    • Patio
    • Grill
    • Satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relish in the luxuries and comforts of this 3-bedroom, 2-bathroom vacation rental house in Litchfield! 'Stone-Peca' is a quintessential New England property that sits on a half acre of land and offers a spacious backyard with a deck and patio. Stylish, high-end decor adorns the interior, making...
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    Litchfield, Connecticut 06750
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Lakeville
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Private Garden
    • Mountain Views
    • Parking
    • Wi-Fi
    • Satellite TV
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    -Salisbury School -Hotchkiss -Indian Mountain School -Lime Rock Park Race Track Just steps to everything in town! Or grab a tall glass of Lemonade and a good book & relax on the porch. This petite in-town home is convenient to restaurants, shops, & Lake. The perfect spot to getaway & enjoy...
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    Lakeville, Connecticut 06039
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    New Preston
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Internet Access
    • Washer
    • Satellite TV
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Visit the beautiful shores of Lake Waramaug in this charming 3-bedroom, 2-bathroom New Preston vacation rental cottage that comfortably sleeps 6. Relax and recharge on the brand new stone patio and spend your days by the water on the private lakefront area and 22 foot dock. With 1,300 square feet...
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    New Preston, Connecticut 06777
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Lakefront 2BR New Marlborough Cottage w/Deck1 / 24
    (1)Excellent
    New Marlborough, MA
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Waterfront
    • Mountain Views
    • Parking
    • DVD Player
    • Central Heating
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Let this serene lake-front Great Barrington area cottage in New Marlborough serve as your ultimate home-away-from-home! Featuring 2 bedrooms, 1-bathroom, and enough room to sleep 4 guests, this property is sure to give you an experience in the Berkshires that you will never forget! THE PROPERTY...
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    New Marlborough, Berkshires 01230
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Short Walk to Lake, Peaceful Getaway, Scenic Views1 / 13
    (3)Excellent
    Granville, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
    • Grill
    • Central Heating
    • Washer
    • Satellite TV
    • DVD Player
    • Housekeeping Included
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 July 2017
    The rental was spacious, immaculate and very comfortable and it's situated in a very private and relaxing part of the forest.
    Reviewed 25 July 2017
    Just what the doctor ordered. Beautiful, peaceful getaway in a lovely private community. Comfortable beds, great kitchen, would DEFINITELY stay again.
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    About this property
    Would you like to spend some time in our cozy retreat in the Berkshires? Our three-bedrooms, two bathrooms house is located in a private community, in the middle of the Tolland state forest , surrounded by the woods and lakes, but at the same time close to major attractions. Fully renovated, the...
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    Granville, Berkshires 01034
    Cabin Holiday Rental - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cornwall Bridge
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Mountain Views
    • DVD Player
    • Hot Tub
    • 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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    Barkhamsted
    6 Bedrooms, 8 Bathrooms, Sleeps 12 Quick View
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    • Balcony
    • Air Conditioning
    • Grill
    • Waterfront
    • Patio
    • Porch
    • Satellite TV
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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,...
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    Barkhamsted, Connecticut 06063
    Holiday Rental House - 6 Bedrooms, 8 Bathrooms, Sleeps 12
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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
    • 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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    West Cornwall
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Washer
    • Air Conditioning
    • 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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    Bethlehem
    5 Bedrooms, 3 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Balcony
    • Grill
    • Terrace
    • Housekeeping Included
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Judd Farm House is situated on 33 acres, the house is in farm country. It is surrounded by rolling hills of Litchfield. There are country roads for walking and biking with very little traffic. It is a perfect retreat for a group there are generous size bedrooms tastlefully decorated. There is a...
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    Bethlehem, Connecticut 06795
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 16
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    Rhubarb Hill, a Charming 1850's Farmhouse1 / 21
    (1)Excellent
    New Preston
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Satellite TV
    • Washer
    • DVD Player
    • Central Heating
    • Wi-Fi
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 July 2014
    We arrived all type A with many plans to hike and swim, ended up enjoying the comfort of the house, cooking, hanging out together. Switching from indoor seating for outdoor...
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    About this property
    Near Lake Waramaug $300 per night with a 3-night minimum $1800 per week. June $6,000 per month July $6,000 per month Aug $6,000 per month Memorial Day to Labor Day $14,000. During the winter months-mid-October-mid-March, I seek long term rentals. I only rent by the month during this...
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    Location Information
    New Preston, Connecticut 06777
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Granby
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Secure Parking
    • Patio
    • Air Conditioning
    • Private Garden
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Wits End Farm1 / 16
    (1)Excellent
    Bethlehem
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Satellite TV
    • Washer
    • Patio
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 August 2017
    Our family stayed at Wits End Farm B&B for a weekend in early June for our son's graduation from a local boarding school. We can't say enough about our time there. Our host...
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    About this property
    This sophisticated and modernized 18th Century rambling farmhouse is set amount towering tress, huge lawns, flower beds, parterre vegetable and herb gardens, 2 ponds, stone walls, pasture and woods. There are five bedrooms, including one huge family suite with a Q bed, twin bed and a crib. All...
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    Bethlehem, Connecticut 06751
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    5BR Woodridge Lake Rental House1 / 17
    (1)Very good
    Goshen
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Outdoor Dining Area
    • Satellite TV
    • DVD Player
    • Internet Access
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Goshen, Connecticut 06756
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Wits End Farm B&B1 / 14
    (1)Excellent
    Bethlehem
    5 Bedrooms, Sleeps 10 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 August 2017
    Our family stayed at Wits End Farm B&B for a weekend in early June for our son's graduation from a local boarding school. We can't say enough about our time there. Our host...
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    About this property
    This sophisticated and modernized 18th Century rambling farmhouse is set amount towering tress, huge lawns, flower beds, parterre vegetable and herb gardens, 2 ponds, stone walls, pasture and woods. There are five bedrooms, including one huge family suite with a Q bed, twin bed and a crib. All...
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    Location Information
    Bethlehem, Connecticut 06751
    Private Room - 5 Bedrooms, Sleeps 10
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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
    • 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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    Location Information
    West Cornwall, Connecticut 06796
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Taconic
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Parking
    • Private Garden
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    North Granby
    2 Bedrooms, 1 Bathroom, Sleeps 4 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
    About this property
    The Windy Top Cottage is an old stone building constructed in 1935 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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    Location Information
    North Granby, Connecticut 06060
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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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    • Private Garden
    • Parking
    • Satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 September 2016
    I only wish my mobility was better to take a walk on this beautiful property very close to Lime Rock Park and many other cultural attractions. Owners were very nice and...
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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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    Quiet first floor apartment in Torrington1 / 12
    (5)Excellent
    Torrington
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Outdoor Dining Area
    • Parking
    • Porch
    • Balcony
    • Terrace
    • Wi-Fi
    • Central Heating
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 September 2017
    The apartment is perfect. The entire place is renovated inside and it is just what Ineeded. There is no other place in Torrington that is this nice and accommodating. Denis...
    Reviewed 3 August 2017
    Denis is a great host, and the apartment is wonderful. To say that it is well appointed is an understatement. It is roomy and light, and the balcony is a plus. It seems that...
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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...
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    Torrington, Connecticut 06790
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    The Cottage at Great Falls1 / 11
    (18)Excellent
    Falls Village
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Satellite TV
    • Washer
    • DVD Player
    • Mountain Views
    • Waterfront
    • Central Heating
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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.
    Reviewed 3 September 2016
    We spent a very relaxing weekend here and took great advantage of the deck overlooking the river. Everything was as described and depicted in photos. It was awesome to hear...
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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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    Location Information
    Falls Village, Connecticut 06031
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Warren
    7 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    • Washer
    • Hot Tub
    • Air Conditioning
    • Waterfront
    • Patio
    • DVD Player
    • Internet Access
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    **Please note that this property can be rented alongside with VRBO listing 3921932ha (Evolve #256841) for discounted rates. Please inquire for additional information** When searching for the perfect place to stay for your next peaceful family gathering, 'Carriage House' is just the spot for you....
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    Location Information
    Warren, Connecticut 06777
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 16
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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
    • Grill
    • 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....
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    Location Information
    New Marlborough, Berkshires 01230
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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