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}
    List your property
    Owner log in
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Update
    Price
    per night
    |||
    |||
    €0
    €273 Average
    €1,000+
    Bedrooms
    Any
    Amenities
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Don't let other travellers get your favourite Winsted area holiday rental. You're so close to securing your perfect getaway. Book today.

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

    1 / 11
    5 of 5 bubbles (1) Excellent
    Falls Village
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    1 / 42
    5 of 5 bubbles (3) Excellent
    Lakeville
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 12
    5 of 5 bubbles (3) Excellent
    Torrington
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 21
    Cornwall Bridge
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • DVD Player
    • Hot Tub
    • Satellite TV
    • Internet Access
    • Private Indoor Pool
    • Air Conditioning
    • Sauna
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    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
    Location Information
    Cornwall Bridge, Connecticut 06754
    1 / 17
    4 of 5 bubbles (1) Very good
    Goshen
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Outdoor Dining Area
    • Satellite TV
    • DVD Player
    • Internet Access
    • Grill
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    1 / 13
    West Cornwall
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Air Conditioning
    • Satellite TV
    • Mountain Views
    • Internet Access
    • Porch
    • DVD Player
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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
    Location Information
    West Cornwall, Connecticut 06796
    1 / 35
    Morris
    3 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Satellite TV
    • Air Conditioning
    • Patio
    • Grill
    • Wi-Fi
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Direct waterfront house with private sandy beach located on the West shoreline of Bantam Lake. Contemporarty A frame style house with 3 bedrooms - 2.5 baths and cozy loft area. All amenities. View all property information
    Location Information
    Morris, Connecticut 06763
    1 / 21
    5 of 5 bubbles (1) Excellent
    New Preston
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Satellite TV
    • Washer
    • DVD Player
    • Central Heating
    • Wi-Fi
    • Balcony
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    New Preston, Connecticut 06777
    5 of 5 bubbles 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...
    See all reviews
    1 / 23
    Lakeville
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Parking
    • Private Garden
    • Satellite TV
    • Air Conditioning
    • Washer
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    -Available Christmas and New Years -3 Ski Mountains nearby. Mohawk, Butternut, Catamount. 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 &... View all property information
    Location Information
    Lakeville, Connecticut 06039
    1 / 11
    5 of 5 bubbles (18) Excellent
    Falls Village
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Balcony
    • Grill
    • Satellite TV
    • Mountain Views
    • Central Heating
    • Hot Tub
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • 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
    Location Information
    Falls Village, Connecticut 06031
    4 of 5 bubbles 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.
    5 of 5 bubbles 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 the...
    See all reviews
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    1 / 37
    5 of 5 bubbles (1) Excellent
    Salisbury
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Wi-Fi
    • Grill
    • Waterfront
    • Mountain Views
    • Outdoor Dining Area
    • DVD Player
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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 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
    Location Information
    Salisbury, Connecticut 06079
    5 of 5 bubbles 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
    1 / 15
    Barkhamsted
    6 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Air Conditioning
    • Grill
    • Waterfront
    • Patio
    • Porch
    • Satellite TV
    • Skiing: Property Is...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    Location Information
    Barkhamsted, Connecticut 06063
    1 / 15
    5 of 5 bubbles (3) Excellent
    Sharon
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Outdoor Dining Area
    • Internet Access
    • Grill
    • DVD Player
    • Air Conditioning
    • Mountain Views
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Want to get away from it all? Just 2 hours away from New York City or Take Metro North and hop in a cab. This house is the perfect getaway located in Sharon, Litchfield County, Connecticut which is in the foothills of the Berkshires. Sharon is the quintessential New England small town. Quiet and... View all property information
    Location Information
    Sharon, Connecticut 06069
    1 / 13
    Granville, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Grill
    • Central Heating
    • Washer
    • Satellite TV
    • DVD Player
    • Housekeeping...
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Granville, Berkshires 01034
    1 / 4
    Torrington
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Waterfront
    • Skiing: Property Is...
    • Hot Tub
    • Housekeeping...
    • DVD Player
    • Mountain Views
    • Sauna
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Located in rural Winchester/Torrington area, this gated property is easy to get to, located on 200 acres of wooded land. It is used primarily as a resort, due to all its amenities, including, Indoor / Outdoor pools, hot tub, exercise room, sauna, indoor/outdoor tennis. It has its own spring fed... View all property information
    Location Information
    Torrington, Connecticut 06790
    1 / 4
    Bloomfield
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Central Heating
    • Washer
    • Porch
    • Parking
    • Private Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Nice get away. Come see our hard wood floors in the living rm, bedrooms (2), with bath & Eat- in kitchen and enjoy your own washer & dryer Hook-Up and storage areas in your own basement. These units are equipped with OIL Heat, Electric hot water and stove. A must see with All Utilities are... View all property information
    Location Information
    Bloomfield, Connecticut 06002
    1 / 16
    Bethlehem
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    • Patio
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Bethlehem, Connecticut 06751
    1 / 62
    Lakeville
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Housekeeping...
    • Grill
    • DVD Player
    • Balcony
    • Central Heating
    • Terrace
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This one of a kind bungalow was built in 1901 but has been extensively renovated to today's standards. Located on 4.5 private acres 5mins from the deepest lake in CT, this home will host up to 12 people with ample room for outside grilling/entertaining. Check us out! You will be pleasantly... View all property information
    Location Information
    Lakeville, Connecticut 06039
    1 / 25
    Warren
    7 Bedrooms, 8 Bathrooms, Sleeps 14 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Hot Tub
    • Air Conditioning
    • Waterfront
    • Patio
    • DVD Player
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    ** Please note that this property can be rented in conjunction with VRBO listing 3921932ha (8 bedrooms, 7.5 bathrooms, Evolve #256841) for discounted rates. These two properties combined will accommodate a total of 30 guests. Please inquire for additional information ** If you’re searching for the... View all property information
    Location Information
    Warren, Connecticut 06777
    1 / 15
    Bethlehem
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Come in, freshen up and enjoy the complimentary snacks and beverages waiting for you in this spacious vaulted ceiling queen bed guest rental in Bethlehem, Connecticut. Our private top floor guest suite is fully equipped for comfort and easy on the budget. The things that are important to you are... View all property information
    Location Information
    Bethlehem, Connecticut 06751
    Get the List
    1 / 20
    Farmington
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Ref # 370406 Because we focus on monthly rentals, we do not accept bookings with a gap between move in date and availability date. We generally require move in dates to be within 7 days of the availability date. Compass Furnished Apartments at this property is located in Farmington, CT, just... View all property information
    Location Information
    Farmington, Connecticut 06032
    1 / 10
    New Marlborough, MA
    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Balcony
    • Central Heating
    • Wi-Fi
    • Grill
    • Washer
    • Terrace
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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.... View all property information
    Location Information
    New Marlborough, Berkshires 01230
    1 / 20
    Farmington
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Ref # 370383 Because we focus on monthly rentals, we do not accept bookings with a gap between move in date and availability date. We generally require move in dates to be within 7 days of the availability date. Compass Furnished Apartments at this property is located in Farmington, CT, just... View all property information
    Location Information
    Farmington, Connecticut 06032
    1 / 14
    Bethlehem
    Private Room, Sleeps 10 | Quick View
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Bethlehem, Connecticut 06751
    1 / 10
    Bloomfield
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Grill
    • Air Conditioning
    • Private Outdoor...
    • Parking
    • Satellite TV
    • Internet Access
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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,... View all property information
    Location Information
    Bloomfield, Connecticut
    1 / 24
    4.5 of 5 bubbles (2) Very good
    West Cornwall
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Internet Access
    • Porch
    • Parking
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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. The brook will dry up during summer dry spells. Located in the beautiful Litchfield Hills, the cottage is 2 minutes from... View all property information
    Location Information
    West Cornwall, Connecticut 06796
    5 of 5 bubbles 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 from...
    4 of 5 bubbles 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
    1 / 3
    Farmington
    6 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
    Show Prices
    Amenities & Details
    • Terrace
    • Patio
    • Air Conditioning
    • Balcony
    • Private Outdoor...
    • Porch
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    Location Information
    Farmington, Connecticut