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 in Winsted

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    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}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    €210 Average
    |||
    |||
    €0€1,000+
    Suitability
    More filters
    Don't let other travellers get your favourite Winsted area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 15 Rentals in Winsted
    Sort by:
    Default
    Winsted
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    The following rentals are within 25 kilometers of Winsted.
    The Cottage at Great Falls1 / 18
    (19)Excellent
    Falls Village
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Quiet first floor apartment in Torrington1 / 12
    (6)Excellent
    Torrington
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Windy Top Stone Cottage1 / 26
    (1)Excellent
    North Granby
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    See all reviews
    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...
    View all property information
    Location Information
    North Granby, Connecticut 06060
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    Riverwood - Cozy Carriage House in the Woods1 / 11
    (1)Excellent
    Falls Village
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    See all reviews
    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....
    View all property information
    Location Information
    Falls Village, Connecticut 06031
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    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
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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!
    See all reviews
    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...
    View all property information
    Location Information
    Granby, Connecticut 06035
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    North Granby
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    North Granby, Connecticut 06060
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Comfortable Rustic Cottage on 4 Wooded Acres with Brook1 / 22
    (3)Very good
    West Cornwall
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    See all reviews
    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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Litchfield House on Half Acre - 1 Mile to Town!1 / 24
    (1)Excellent
    Litchfield
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 November 2017
    Litchfield is a charming small town that is a popular weekend destination for New Yorkers. It has a few good restaurants and boutique shopping, plus the interesting historical...
    See all reviews
    About this property
    Relish in the luxuries and comforts of this 3-bedroom, 2-bath vacation rental house in Litchfield! 'Stone-Peca' is a quintessential New England property sitting on a half acre of land, offering a 4-season sun porch as well as a spacious backyard with a deck and patio. Stylish, high-end decor adorns...
    View all property information
    Location Information
    Litchfield, Connecticut 06750
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Enquiry
    Colebrook
    3 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Private Garden
    • Air Conditioning
    • Washer
    • Grill
    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...
    View all property information
    Location Information
    Colebrook, Connecticut 06021
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 12
    Make Enquiry
    Save time - get the best Winsted rentals sent straight to your email!
    Get the List
    West Cornwall
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    West Cornwall, Connecticut 06796
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    Harwinton
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Parking
    Suitability
    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...
    View all property information
    Location Information
    Harwinton, Connecticut 06791
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    West Hartland
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Elevate your lakeside retreat at this 3-bedroom, 2-bathroom vacation rental home that has accommodations for 8 in Tolland. Dive into lakeside fun on your private dock and hop on a kayak or stand-up paddleboard for a day of exploring this peaceful lake. When you’re not at the lake, enjoy fabulous...
    View all property information
    Location Information
    West Hartland, Connecticut 01034
    Cabin Holiday Rental - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Canton
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the beauty of Connecticut from this 4-bed, 2-bath vacation rental house in Canton! Easily sleeping up to 8 guests, this spacious house combines all of the comforts of home with the amenities you desire, including a furnished porch and sauna. Whether you come to ski the slopes of Sundown...
    View all property information
    Location Information
    Canton, Connecticut 06019
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Norfolk
    4 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Skiing: Property Is In A Ski Resort
    • Central Heating
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the bucolic getaway you've been craving with a stay at this 4-bed, 1.5-bath Norfolk house! Truly off-the-grid, this vacation rental is void of all modern distractions, but complete with a fully equipped kitchen, charcoal grill, furnished patio and 2 gas stoves - creating a peaceful...
    View all property information
    Location Information
    Norfolk, Connecticut 06058
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Enquiry
    List your property
    Owner log in