Title: Book the Best Winsted LUXURY Hotels - Upscale Hotels in Winsted, CT | Expedia.ca [Hotels in Winsted](https://expedia.ca/Winsted-Hotels.d3000430645.Travel-Guide-Hotels)[Vacation Rentals in Winsted](https://expedia.ca/Winsted-Vacation-Rentals.d3000430645.Travel-Guide-VacationRentals)[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) ![A tractor up a tree! And, there's a picnic table underneath.](https://images.trvl-media.com/place/6125522/bf8d15d8-5a06-4bf9-b059-b9dc4d18a280.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Kim Knox Beckius ![](https://images.trvl-media.com/place/6125522/bf8d15d8-5a06-4bf9-b059-b9dc4d18a280.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 availability on Winsted Luxury Hotels Tonight [Jan 20 - Jan 21](https://www.expedia.ca/Hotel-Search?regionId=3000430645&startDate=2026-01-20&endDate=2026-01-21&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Jan 21 - Jan 22](https://www.expedia.ca/Hotel-Search?regionId=3000430645&startDate=2026-01-21&endDate=2026-01-22&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) This weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=3000430645&startDate=2026-01-23&endDate=2026-01-25&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=3000430645&startDate=2026-01-30&endDate=2026-02-01&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Top Winsted Hotel Reviews ![Simsbury 1820 House](https://images.trvl-media.com/lodging/1000000/50000/42300/42279/6326a611_y.jpg) ### Simsbury 1820 House 10/10 Excellent "lovely hotel" [](https://expedia.ca/Hartford-Hotels-Simsbury-1820-House.h42279.Hotel-Information) ![DoubleTree by Hilton Hotel Bristol, Connecticut](https://images.trvl-media.com/lodging/1000000/10000/5300/5265/7a34507b_y.jpg) ### DoubleTree by Hilton Hotel Bristol, Connecticut 10/10 Excellent "clean room, quiet overnight, great hot tub " [](https://expedia.ca/Hartford-Hotels-DoubleTree-By-Hilton-Hotel-Bristol.h5265.Hotel-Information) ![The Farmington Inn & Suites](https://images.trvl-media.com/lodging/1000000/20000/10200/10185/1c89931a_y.jpg) ### The Farmington Inn & Suites 10/10 Excellent "The staff were very helpful.The had a great breakfast and clean tables. The room was very clean.They had coffee and flavored drinks at a station when you came in.This was a very good stay." [](https://expedia.ca/Hartford-Hotels-The-Farmington-Inn-Suites.h10185.Hotel-Information) ![Holiday Inn Express Hotel & Suites Great Barrington by IHG](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG 10/10 Excellent "everything" [](https://expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ![Quality Inn](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg) ### Quality Inn 10/10 Excellent "Great place to stay if you enjoy paying less money and still sleeping well. Inexpensive, clean, quiet, and ridiculously convenient—just a short two-block stroll to the downtown strip for shopping and restaurants (close enough to walk, far enough to avoid the noise). Only 2.5 miles down a local road to Butternut ski mountain, so you’ll be on the slopes before your coffee fully kicks in. CVS shares the same parking lot, which is perfect in case you forget toothpaste, sunscreen, or your dignity. Most importantly—and let’s be honest, this matters—a beer, wine, liquor, and cheese shop is only one mile down the road. Priorities are clearly respected here. Rooms are clean, beds are super comfortable, and the décor politely reminds you that time exists. Free breakfast is solid but not life-changing: eggs, toast, sausage, waffles, yogurt, coffee, fruit—everything you need to function, nothing you’ll write poetry about. Bathroom fans are loud, but they drown out the 1 time per day freight train in the back yard, so net positive. Overall, a great stay, and for the cheap nightly price, it’s basically unbeatable unless you’re expecting chandeliers and a personal butler. Enjoy! " [](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information) ![The Litchfield Inn](https://images.trvl-media.com/lodging/5000000/4980000/4978900/4978856/9aa3fa98_y.jpg) ### The Litchfield Inn 10/10 Excellent "Very good. Nice selection " [](https://expedia.ca/Torrington-Hotels-The-Litchfield-Inn.h4978856.Hotel-Information) ![Sheraton Hartford Hotel at Bradley Airport](https://images.trvl-media.com/lodging/1000000/10000/4700/4632/c8edc11d_y.jpg) ### Sheraton Hartford Hotel at Bradley Airport 10/10 Excellent "Perfect stay before a long flight. " [](https://expedia.ca/Hartford-Hotels-Sheraton-Hartford-Hotel-At-Bradley-Airport.h4632.Hotel-Information) ![Avon Old Farms Hotel](https://images.trvl-media.com/lodging/1000000/10000/2700/2635/d997675e_y.jpg) ### Avon Old Farms Hotel 10/10 Excellent "Charming and relaxing ambience" [](https://expedia.ca/Hartford-Hotels-Avon-Old-Farms-Hotel.h2635.Hotel-Information) ## Frequently asked questions ### Are you looking for a luxury hotel for your Winsted vacation? ### What's the best high-end hotel in Winsted? ### When can I expect good weather in Winsted? ### What's there to see and do in Winsted? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [Business Hotels in Barkhamsted ](https://www.expedia.ca/Barkhamsted-Hotels-Business-Hotel.0-0-d6359343-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Barkhamsted ](https://www.expedia.ca/Barkhamsted-Hotels-Cheap-Hotels.0-0-d6359343-tCheapHotels.Travel-Guide-Filter-Hotels) - [Motels in Barkhamsted ](https://www.expedia.ca/Barkhamsted-Motels.d6359343-aaMotels.Travel-Guide-Accommodation) - 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