We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals and Homes in Winsted, CT

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    Payment Protection
    Use a credit card to book with our Peace of Mind Protection.Learn more
    Find a rental
    Price per night
    Min
    to
    Max
    Bedrooms
    Any
    Amenities
    Select
    Payment
    Select
    Go to map view
    More filters
    Find more rentals you can book on TripAdvisor!   We're showing you properties you can book on TripAdvisor first.
    All 21 Rentals in the Winsted Area
    loading...
    Sort by

    The following rentals are within 30 kilometers of Winsted, Connecticut.

    From
    €182
    / Night
    Payment Protection
    View Details
    1 / 15
    5 of 5 stars (3) Excellent
    Sharon
    3 Bedrooms / 1 Bathroom / Sleeps 5
    Overview Reviews (3) Make Enquiry
    From
    €1,004
    / Week
    Payment Protection
    View Details
    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
    From
    €57
    / Night
    Payment Protection
    View Details
    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
    From
    €228
    / Night
    Payment Protection
    View Details
    1 / 19
    5 of 5 stars (3) Excellent
    Lakeville
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    traveller have booked this property
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    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
    Make Enquiry
    5 of 5 stars Reviewed 27 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...
    5 of 5 stars 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...
    See all reviews
    From
    €130
    / Night
    Payment Protection
    View Details
    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
    Make Enquiry
    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...
    See all reviews
    From
    €137
    / Night
    Payment Protection
    View Details
    1 / 37
    5 of 5 stars (1) Excellent
    Salisbury
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    traveller have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    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 17 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
    Make Enquiry
    5 of 5 stars 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 pace...
    See all reviews
    From
    €228
    / Night
    Payment Protection
    View Details
    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 Lakefront, 4 bedrooms, 3 baths, 3 guest rooms, open floor plan with kitchen, living and dining areas, family room, sports room, deck, two balconies and patio. The house has a unique setting in the heart of a nature... View all property information
    Make Enquiry
    From
    €274
    / Night
    Payment Protection
    View Details
    1 / 10
    Norfolk
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    traveller have booked this property
    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
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This newly renovated 1850's farmhouse in charming, rural Northwest CT has warmth and privacy galore! The home is located on eight acres of land on a dead end road, but is only 4 miles from the center of town! There are three bedrooms, a laundry closet, and 2 full baths upstairs. A jacuzzi... View all property information
    Make Enquiry
    From
    €228
    / Night
    Payment Protection
    View Details
    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
    Make Enquiry
    From
    €342
    / Night
    Payment Protection
    View Details
    1 / 13
    West Cornwall
    3 Bedrooms / 3 Bathrooms / Sleeps 10
    traveller 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
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    From
    €46
    / Night
    Payment Protection
    View Details
    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
    Make Enquiry
    From
    €821
    / Night
    Payment Protection
    View Details
    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
    Make Enquiry
    From
    €137
    / Night
    Payment Protection
    View Details
    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
    Make Enquiry
    From
    €456
    / Night
    Payment Protection
    View Details
    1 / 18
    Litchfield
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Housekeeping...
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Our home is on Woodridge Lake, a private lake community in the town of Goshen in Litchfield County CT. The house is walking distance (about 200 yards) to the clubhouse area which includes 8 tennis courts, a pool (summer), beach, basketball court, fitness center, snack bar (summer). **We are... View all property information
    Make Enquiry
    From
    €59
    / Night
    Payment Protection
    View Details
    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
    Make Enquiry
    From
    €82
    / Night
    Payment Protection
    View Details
    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
    Make Enquiry
    From
    €269
    / Night
    Payment Protection
    View Details
    1 / 20
    New Hartford
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    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
    Make Enquiry
    From
    €182
    / Night
    View Details
    1 / 11
    5 of 5 stars (13) Excellent
    Falls Village
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (13) 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
    Make Enquiry
    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...
    5 of 5 stars Reviewed 18 January 2015
    Perfect getaway location with all the amenities – including a fireplace for a perfect winter stay. The cottage was clean and inviting, and the character of the furnishings and...
    See all reviews
    From
    €137
    / Night
    View Details
    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
    Winter activities: The cottage is 10 minutes from the Mohawk Mountain Ski Area - 5 trails, 4 lifts and $30 lift tickets; and 45 minutes from Butternut Basin in Great Barrington, MA, and Catamount Ski Area in Hillsdale, NY. Other nearby winter activity includes: walking along Upper River Road... View all property information
    Make Enquiry
    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...
    See all reviews
    From
    €912
    / Night
    View Details
    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
    Make Enquiry
    Get the List
    From
    €543
    / Night
    Payment Protection
    View Details
    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
    Make Enquiry