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Holiday Rentals and Homes in Winsted, CT

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    All 21 Rentals in the Winsted Area
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    The following rentals are within 30 kilometers of Winsted, Connecticut.

    From
    €224
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    1 / 19
    5 of 5 stars (3) Excellent
    Lakeville
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    traveller have booked this property
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    €134
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    1 / 37
    5 of 5 stars (1) Excellent
    Salisbury
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    traveller have booked this property
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    €179
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    1 / 15
    5 of 5 stars (3) Excellent
    Sharon
    3 Bedrooms / 1 Bathroom / Sleeps 5
    Overview Reviews (3) Make Enquiry
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    €985
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    1 / 17
    4 of 5 stars (1) Very good
    Goshen
    5 Bedrooms / 4 Bathrooms / Sleeps 12
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Gym
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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
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    €128
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    1 / 15
    5 of 5 stars (1) Excellent
    Sandisfield, MA
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Home on 2.5 wooded acres in a private lake community, with vacant wooded acres on both sides. Amenities of the community include non-motor boat lake, outdoor heated swimming pool, tennis courts, exercise facility, clubhouse and walking trails. The home is located in the Berkshires, a popular year... View all property information
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    5 of 5 stars Reviewed 1 February 2015
    We stayed at this beautiful house in a lovely lake community. The house is open and bright and very comfortable. We spent most of our time on the large screened back porch...
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    €269
    / Night
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    1 / 20
    5 of 5 stars (1) Excellent
    New Preston
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    traveller have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Near Lake Waramaug $300 per night with a 3-night minimum $1800 per week. June $5,000 per month July $5,000 per month Aug $6,000 per month Memorial Day to Labor Day $12,000 Enjoy this green woodsy retreat in beautiful Litchfield County and relax in a charming farmhouse that is spacious... View all property information
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    5 of 5 stars 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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    €672
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    1 / 20
    Cornwall Bridge
    3 Bedrooms / 3 Bathrooms / Sleeps 7
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Mountain Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    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.... View all property information
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    From
    €336
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    1 / 13
    West Cornwall
    3 Bedrooms / 3 Bathrooms / Sleeps 10
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    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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    From
    €806
    / Night
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    1 / 16
    Bethlehem
    6 Bedrooms / 4 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Gym
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    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... View all property information
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    From
    €224
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    1 / 5
    Granville, MA
    5 Bedrooms / 3 Bathrooms / Sleeps 12
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    4 Bedrooms, 3 Baths, 3 Guest Rooms, Open Floor Plan Kitchen, Living, Dining 4 Bedrooms, 3 Baths, 3 Guest Rooms, Open Floor Plan Kitchen, Living, Dining Lakefront, 4 bedrooms, 3 baths, 3 guest rooms, open floor plan with kitchen, living and dining areas, family room, sports room, deck, two... View all property information
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    From
    €533
    / Night
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    1 / 15
    Barkhamsted
    6 Bedrooms / 8 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Fireplace
    • Grill
    • Satellite TV
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    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
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    From
    €81
    / Night
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    1 / 8
    Torrington
    1 Bedroom / 1 Bathroom / Sleeps 2
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Internet Access
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    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
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    From
    €45
    / Night
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    1 / 15
    Plymouth
    8 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    This beatuiful 8 room Raised Ranch is located on a quiet dead end street. Home is very spacious with a new efficient oil based heating system. Large eat in kitchen with appliances. Large dining room with sliders to two tier deck overlooking a 1 acre lot. Living room is large with fireplace.... View all property information
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    From
    €134
    / Night
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    1 / 1
    Goshen
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Reserve your get-away for 2014 at the best lake resort community in NW Connecticut, Woodridge Lake ! This property books quickly and far in advance during the summer season and is very popular with families ! We are offering as a seasonal monthly rental this 3 bedroom 2 bath home nestled in the... View all property information
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    From
    €354
    / Night
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    1 / 20
    New Hartford
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Come enjoy a stay in this newly remodeled waterfront property on West Hill Lake in Litchfield County. Located on 4+ acres, 3 wooded, this 4bed/3bath 2600+ square foot home can comfortably accommodate up to 8 guests. Beautifully appointed, the features include; wood burning fireplace, marble... View all property information
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    From
    €224
    / Night
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    1 / 14
    New Preston
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    'Little Wheel' is the guest cottage on the historic Riverdance MIll property (circa 1875) in the charming village of New Preston, CT. The cottage has been totally reconstructed recently. It is bright and airy in the Spring and Summer, cozy and warm in the Fall and Winter and ALWAYS romantic! The... View all property information
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    From
    €58
    / Night
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    1 / 7
    Bristol
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Internet Access
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Located in 1880 home in older quiet neighborhood .Nearby park to walk in. Located 2 miles from ESPN and the great Lake Compounce amusement park. Walking distance to clock museum, shopping, library and churches. Short drive to carousel museum. 13 miles from capital of Hartford. Off street... View all property information
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    From
    €179
    / Night
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    1 / 11
    5 of 5 stars (14) Excellent
    Falls Village
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (14) Make Enquiry
    Amenities & Details
    • Balcony
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Mountain Views
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    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
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    5 of 5 stars Reviewed 9 April 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...
    5 of 5 stars Reviewed 15 February 2015
    Went with the girlfriend for a weekend getaway and chose the perfect place. Extremely relaxing and soothing trip. Everything you need is there, french press? Yep. Towels? Yep...
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    From
    €134
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    1 / 22
    4 of 5 stars (1) Very good
    West Cornwall
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    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
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    4 of 5 stars 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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    From
    €895
    / Night
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    1 / 3
    Farmington
    6 Bedrooms / 8 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Fireplace
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    magnificant French Normandy hillside all brick 6 bedroom 7.5 bath custom Mansion with 3.5 acres beautiful, lush, private, exclusive ESTATE, in prestigious FARMINGTON, CT. Just at I-84, Exit 39. May be leased for long weekends, weekly or long term stay. . 6 bedrooms, 7.5 baths, swimming pool,... View all property information
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    From
    €336
    / Night
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    1 / 8
    Southfield, MA
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Grill
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Peaceful home set on 3-acres with mountain views and a sunny Southern exposure. Kitchen is oversized with an eating area and a breakfast bar. Front porch and patio, master bedroom with ample storage and private bath with soaking tub. Extra rooms for work or play space. Attached two car garage... View all property information
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