Title: Winsted Vacation Rentals from CA $367: Short-Term Rentals for 2025 | Expedia.ca [Hotels in Winsted](https://expedia.ca/Winsted-Hotels.d3000430645.Travel-Guide-Hotels)[Winsted Car Rentals](https://expedia.ca/Car-Rentals-In-Winsted.d3000430645.Car-Rental-Guide)[Winsted Vacation Packages](https://expedia.ca/Winsted.d3000430645.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/b24f1cfa2ac11e9ccb5cb3de60b30e98.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Kim Knox Beckius # Winsted Vacation Rentals - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Tonight [Nov 10 - Nov 11](https://www.expedia.ca/Hotel-Search?regionId=3000430645&startDate=2025-11-10&endDate=2025-11-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 11 - Nov 12](https://www.expedia.ca/Hotel-Search?regionId=3000430645&startDate=2025-11-11&endDate=2025-11-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=3000430645&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=3000430645&startDate=2025-11-21&endDate=2025-11-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Vacation Rentals in Winsted ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinsted-Vacation-Rentals.d3000430645.Travel-Guide-VacationRentals)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinsted-Vacation-Rentals.d3000430645.Travel-Guide-VacationRentals) ## Top Winsted Hotel Reviews ![DoubleTree by Hilton Hartford - Bradley Airport](//images.trvl-media.com/lodging/1000000/20000/14500/14480/775bdf7d_y.jpg) ### DoubleTree by Hilton Hartford - Bradley Airport 10/10 Excellent "The staff was very friendly. We also enjoyed the location in our room very much." [](https://expedia.ca/Hartford-Hotels-DoubleTree-By-Hilton-Hartford-Bradley-Airport.h14480.Hotel-Information) ![Holiday Inn Express Hotel & Suites Great Barrington by IHG](//images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG 10/10 Excellent "Early check in." [](https://expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ![Sheraton Hartford Hotel at Bradley Airport](//images.trvl-media.com/lodging/1000000/10000/4700/4632/c8edc11d_y.jpg) ### Sheraton Hartford Hotel at Bradley Airport 10/10 Excellent "Great hotel, comfy bed and convenient." [](https://expedia.ca/Hartford-Hotels-Sheraton-Hartford-Hotel-At-Bradley-Airport.h4632.Hotel-Information) ![Simsbury 1820 House](//images.trvl-media.com/lodging/1000000/50000/42300/42279/6326a611_y.jpg) ### Simsbury 1820 House 10/10 Excellent "All the staff were incredibly courteous, and the unlimited free bottled water was a nice touch. Overall, an awesome property and a great experience!" [](https://expedia.ca/Hartford-Hotels-Simsbury-1820-House.h42279.Hotel-Information) ![Hampton Inn & Suites Hartford/Farmington](//images.trvl-media.com/lodging/3000000/2980000/2970600/2970540/393f3b68_y.jpg) ### Hampton Inn & Suites Hartford/Farmington 10/10 Excellent "The hotel always smelled really nice! It was very clean." [](https://expedia.ca/Hartford-Hotels-Hampton-Inn-And-Suites-HartfordFarmington.h2970540.Hotel-Information) ![DoubleTree by Hilton Hotel Bristol, Connecticut](//images.trvl-media.com/lodging/1000000/10000/5300/5265/7a34507b_y.jpg) ### DoubleTree by Hilton Hotel Bristol, Connecticut 10/10 Excellent "Amazing stay" [](https://expedia.ca/Hartford-Hotels-DoubleTree-By-Hilton-Hotel-Bristol.h5265.Hotel-Information) ![Quality Inn](//images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg) ### Quality Inn 10/10 Excellent "The staff was amazing, so kind and accommodating. The room was clean, the beds were very comfortable. Nice breakfast options. We were in town for a concert at Mahaiwe and we didn’t use our car once we checked in… a great home base for the weekend. Will definitely be back. " [](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information) ![Avon Old Farms Hotel](//images.trvl-media.com/lodging/1000000/10000/2700/2635/d997675e_y.jpg) ### Avon Old Farms Hotel 10/10 Excellent "This is a beautiful classic hotel with impeccable service. The grounds are so gorgeous! " [](https://expedia.ca/Hartford-Hotels-Avon-Old-Farms-Hotel.h2635.Hotel-Information) ![Delamar West Hartford](//images.trvl-media.com/lodging/19000000/18170000/18166800/18166744/d809cec2_y.jpg) ### Delamar West Hartford 10/10 Excellent "Beautiful hotel in a perfect location. " [](https://expedia.ca/Hartford-Hotels-Delamar-West-Hartford.h18166744.Hotel-Information) ## Find out more about Winsted **Everything you need to know about** **Winsted** **vacation rentals** Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winsted vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on! There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winsted vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.  **Winsted vacation rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Winsted. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in .  Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winsted vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winsted vacation rentals we have selected for you start as low as CA $367 per night. Entering your travel dates in the search wizard you might find even better deals! **How to find incredible deals on Winsted rentals** At Expedia, we put the best Winsted vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.  To find some top Winsted rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winsted vacation. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winsted. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.  ## Explore a world of travel with Expedia - Trending destinations on Expedia.ca - All accommodation types in Winsted ### Trending destinations on Expedia.ca - [Canmore Vacation Rentals](https://www.expedia.ca/Canmore-Vacation-Rentals.d10131.Travel-Guide-VacationRentals) - [Maui Vacation Rentals](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals) - [Kelowna Vacation Rentals](https://www.expedia.ca/Kelowna-Vacation-Rentals.d3997.Travel-Guide-VacationRentals) - [Whistler Vacation Rentals](https://www.expedia.ca/Whistler-Vacation-Rentals.d4115.Travel-Guide-VacationRentals) - [Florida Vacation Rentals](https://www.expedia.ca/Destinations-In-Florida.d211.Vacation-Rental-Destinations) - [Victoria Vacation Rentals](https://www.expedia.ca/Victoria-Vacation-Rentals.d4138.Travel-Guide-VacationRentals) - [Vancouver Vacation Rentals](https://www.expedia.ca/Vancouver-Vacation-Rentals.d178315.Travel-Guide-VacationRentals) - [Palm Springs Vacation Rentals](https://www.expedia.ca/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals) - [Tofino Vacation Rentals](https://www.expedia.ca/Tofino-Vacation-Rentals.d6094955.Travel-Guide-VacationRentals) - [Calgary Vacation Rentals](https://www.expedia.ca/Calgary-Vacation-Rentals.d178245.Travel-Guide-VacationRentals) - [Costa Rica Vacation Rentals](https://www.expedia.ca/Destinations-In-Costa-Rica.d42.Vacation-Rental-Destinations) - [Vancouver Island Vacation Rentals](https://www.expedia.ca/Vancouver-Island-Vacation-Rentals.d6058387.Travel-Guide-VacationRentals) - [Puerto Vallarta Vacation Rentals](https://www.expedia.ca/Puerto-Vallarta-Vacation-Rentals.d180016.Travel-Guide-VacationRentals) - [Hawaii Vacation Rentals](https://www.expedia.ca/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations) - [Toronto Vacation Rentals](https://www.expedia.ca/Toronto-Vacation-Rentals.d178314.Travel-Guide-VacationRentals) - [Banff Vacation Rentals](https://www.expedia.ca/Banff-Vacation-Rentals.d10550.Travel-Guide-VacationRentals) - [Penticton Vacation Rentals](https://www.expedia.ca/Penticton-Vacation-Rentals.d4135.Travel-Guide-VacationRentals) - [Osoyoos Vacation Rentals](https://www.expedia.ca/Osoyoos-Vacation-Rentals.d181782.Travel-Guide-VacationRentals) - [Mont Tremblant Vacation Rentals](https://www.expedia.ca/Mont-Tremblant-Vacation-Rentals.d55374.Travel-Guide-VacationRentals) - [Big White Ski Resort Vacation Rentals](https://www.expedia.ca/Big-White-Ski-Resort-Vacation-Rentals.d6058319.Travel-Guide-VacationRentals) - [Ontario Vacation Rentals](https://www.expedia.ca/Destinations-In-Ontario.d11178.Vacation-Rental-Destinations) - [British Columbia Vacation Rentals](https://www.expedia.ca/Destinations-In-British-Columbia.d11117.Vacation-Rental-Destinations) - [Prince Edward Island Vacation Rentals](https://www.expedia.ca/Destinations-In-Prince-Edward-Island.d6058122.Vacation-Rental-Destinations) - [Québec Vacation Rentals](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals) - [Vacation Homes in Winsted](https://expedia.ca/Winsted-Private-Vacation-Homes.d3000430645-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Cottages in Winsted](https://expedia.ca/Winsted-Cottages.d3000430645-aaCottages.Travel-Guide-Accommodation) - [Apartments in Winsted](https://expedia.ca/Winsted-Apartments.d3000430645-aaApartments.Travel-Guide-Accommodation) - [Cabin Rentals in Winsted](https://expedia.ca/Winsted-Cabins.d3000430645-aaCabins.Travel-Guide-Accommodation) - [Farmstay in Winsted](https://expedia.ca/Winsted-Agritourism.d3000430645-aaAgritourism.Travel-Guide-Accommodation) - [Motels in Winsted](https://expedia.ca/Winsted-Motels.d3000430645-aaMotels.Travel-Guide-Accommodation) - [B&B in Winsted](https://expedia.ca/Winsted-Bed-And-Breakfast.d3000430645-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Winsted](https://expedia.ca/Winsted-Guest-Houses.d3000430645-aaGuestHouses.Travel-Guide-Accommodation) - [Inns in Winsted](https://expedia.ca/Winsted-Inns.d3000430645-aaInns.Travel-Guide-Accommodation) - [Chalets in Winsted](https://expedia.ca/Winsted-Chalets.d3000430645-aaChalets.Travel-Guide-Accommodation) - [Condo Rentals in Winsted](https://expedia.ca/Winsted-Condos.d3000430645-aaCondos.Travel-Guide-Accommodation) - [Resorts in Winsted](https://expedia.ca/Winsted-Resort-Hotels.d3000430645-aaResortHotels.Travel-Guide-Accommodation) - [Lodges in Winsted](https://expedia.ca/Winsted-Lodges.d3000430645-aaLodges.Travel-Guide-Accommodation) - [Villas in Winsted](https://expedia.ca/Winsted-Villas.d3000430645-aaVillas.Travel-Guide-Accommodation) ## Frequently asked questions ### Can I find vacation rentals in Winsted? > Yes, we have vacation rentals in Winsted close to Laurel Lanes, or you can go with a more secluded option if you're looking for extra privacy while you relax. ### What are some of the best vacation home rentals that Winsted has to offer? > [Peace and quiet on the lake](https://www.expedia.ca/Becket-Hotels-Peace-And-Quiet-On-The-Lake.h30777071.Hotel-Information): Visitors like this Winsted vacation home rental. It is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind. ### How many vacation rentals are there in Winsted? > With 7 Expedia vacation rentals, you're sure to find just the right place for your Winsted stay. ### What’s there to see and do in Winsted? > Highland Lake and Rowley Fields are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Laurel Lanes. While here, Burr Pond State Park and Winchester Historical Society are other places worth a visit. ### What are vacation rentals like in Winsted? > Vacation rentals are private properties you can stay in for several days or longer in Winsted. Vacation rentals feature amenities like WiFi and washers and dryers so you'll have everything you need. If you're concerned about cleanliness, a vacation rental can provide a sense of seclusion away from shared hotel elevators and bustling concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for family gatherings. ### Expedia's Latest Trends Hotels - [Hotels in Honolulu](https://expedia.ca/Honolulu-Hotels.d1488.Travel-Guide-Hotels) - [Hotels in Bangor](https://expedia.ca/Bangor-Hotels.d6050918.Travel-Guide-Hotels) - [Hotels in Mystic](https://expedia.ca/Mystic-Hotels.d9007.Travel-Guide-Hotels) - [Hotels in Grand Forks](https://expedia.ca/Grand-Forks-Hotels.d1312.Travel-Guide-Hotels) - [Hotels in Kalispell](https://expedia.ca/Kalispell-Hotels.d6056415.Travel-Guide-Hotels) - [Hotels in Fargo](https://expedia.ca/Fargo-Hotels.d6059376.Travel-Guide-Hotels) - [Hotels in New Haven](https://expedia.ca/New-Haven-Hotels.d180036.Travel-Guide-Hotels) - [Hotels in Hartford](https://expedia.ca/Hartford-Hotels.d180005.Travel-Guide-Hotels) - [Hotels in Norwalk](https://expedia.ca/Norwalk-Hotels.d9245.Travel-Guide-Hotels) - [Hotels in Palm Springs](https://expedia.ca/Palm-Springs-Hotels.d180676.Travel-Guide-Hotels) - [Hotels in Stamford](https://expedia.ca/Stamford-Hotels.d602523.Travel-Guide-Hotels) - [Hotels in Danbury](https://expedia.ca/Danbury-Hotels.d6046722.Travel-Guide-Hotels) - [Hotels in Bridgeport](https://expedia.ca/Bridgeport-Hotels.d525.Travel-Guide-Hotels) - [Hotels in Stratford](https://expedia.ca/Stratford-Hotels.d8127.Travel-Guide-Hotels) Flights - [Flights to New Haven](https://expedia.ca/Cheap-Flights-To-New-Haven.d180036.Travel-Guide-Flights) - [Flights to Stamford](https://expedia.ca/Cheap-Flights-To-Stamford.d602523.Travel-Guide-Flights) - [Flights to Palm Springs](https://expedia.ca/Cheap-Flights-To-Palm-Springs.d180676.Travel-Guide-Flights) Cars - [Car rentals in Palm Springs](https://expedia.ca/Car-Rentals-In-Palm-Springs.d180676.Car-Rental-Guide) Activities - [Things to do in New Haven](https://expedia.ca/Things-To-Do-In-New-Haven.d180036.Travel-Guide-Activities) - [Things to do in Hartford](https://expedia.ca/Things-To-Do-In-Hartford.d180005.Travel-Guide-Activities) - [Things to do in Stamford](https://expedia.ca/Things-To-Do-In-Stamford.d602523.Travel-Guide-Activities) Packages - [Disney Vacations](https://expedia.ca/Disney.d3000453867.Destination-Travel-Guides) - [Honolulu Vacations](https://expedia.ca/Honolulu.d1488.Destination-Travel-Guides) - [Central Vacations](https://expedia.ca/Central.d10503.Destination-Travel-Guides) - [Canadian Vacations](https://expedia.ca/Canadian.d6127256.Destination-Travel-Guides) General - [Visit Danbury](https://expedia.ca/Danbury.dx6046722) - [Visit Bridgeport](https://expedia.ca/Bridgeport.dx525) - [Visit New Haven](https://expedia.ca/New-Haven.dx180036) - [Visit Hartford](https://expedia.ca/Hartford.dx180005) - [Visit Branford](https://expedia.ca/Branford.dx6243) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)