Title: 5 Stars Hotels in Winsted, Connecticut from CA $169 - Find Cheap Winsted Hotels With 5 Stars | Expedia.ca [Winsted Travel Guide](https://expedia.ca/Winsted.dx3000430645)[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)[Flights to Winsted](https://expedia.ca/Cheap-Flights-To-Winsted.d3000430645.Travel-Guide-Flights)[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 # 5 Stars Hotels in Winsted, Connecticut from CA $169 - ![](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 5 Star Hotels Tonight [Dec 13 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=3000430645&startDate=2025-12-13&endDate=2025-12-14&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 14 - Dec 15](https://www.expedia.ca/Hotel-Search?regionId=3000430645&startDate=2025-12-14&endDate=2025-12-15&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=3000430645&startDate=2025-12-19&endDate=2025-12-21&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=3000430645&startDate=2025-12-26&endDate=2025-12-28&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winsted 5-star hotels ![Exterior](https://images.trvl-media.com/lodging/22000000/21770000/21767700/21767645/4a6d4a2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (Century Lodge)](https://images.trvl-media.com/lodging/22000000/21770000/21767700/21767645/30a1b181.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/22000000/21770000/21767700/21767645/2026466d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/22000000/21770000/21767700/21767645/b8578f99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Troutbeck [](https://www.expedia.ca/Amenia-Hotels-Troutbeck.h21767645.Hotel-Information) Amenia [](https://www.expedia.ca/Amenia-Hotels-Troutbeck.h21767645.Hotel-Information) ![Family House](https://images.trvl-media.com/lodging/71000000/70550000/70549400/70549365/ff59e7a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach nearby, beach towels, fishing](https://images.trvl-media.com/lodging/71000000/70550000/70549400/70549365/f37bc34c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/71000000/70550000/70549400/70549365/077958ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/71000000/70550000/70549400/70549365/0802bc3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Las Flores Villa [](https://www.expedia.ca/New-Preston-Hotels-Las-Flores-Villa.h70549365.Hotel-Information) New Preston 10/10 Exceptional (1) [](https://www.expedia.ca/New-Preston-Hotels-Las-Flores-Villa.h70549365.Hotel-Information) ![](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%2F5Star-Winsted-Hotels.s50-0-d3000430645.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Winsted-Hotels.s50-0-d3000430645.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Winsted. ![DoubleTree by Hilton Hartford - Bradley Airport](https://images.trvl-media.com/lodging/1000000/20000/14500/14480/775bdf7d_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### DoubleTree by Hilton Hartford - Bradley Airport 16 Ella T. Grasso Turnpike Windsor Locks CT CA $147 CA $169 total Dec 24 - Dec 25 includes taxes & fees 8/10 Very Good! (1,000 reviews) [](https://expedia.ca/Hartford-Hotels-DoubleTree-By-Hilton-Hartford-Bradley-Airport.h14480.Hotel-Information) ![Delamar West Hartford](https://images.trvl-media.com/lodging/19000000/18170000/18166800/18166744/d809cec2_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Delamar West Hartford 1 Memorial Road West Hartford CT CA $389 CA $468 total Dec 29 - Dec 30 includes taxes & fees 9.6/10 Exceptional! (1,000 reviews) [](https://expedia.ca/Hartford-Hotels-Delamar-West-Hartford.h18166744.Hotel-Information) ![DoubleTree by Hilton Hotel Bristol, Connecticut](https://images.trvl-media.com/lodging/1000000/10000/5300/5265/7a34507b_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### DoubleTree by Hilton Hotel Bristol, Connecticut 42 Century Dr Bristol CT CA $191 CA $220 total Dec 21 - Dec 22 includes taxes & fees 9/10 Wonderful! (1,002 reviews) [](https://expedia.ca/Hartford-Hotels-DoubleTree-By-Hilton-Hotel-Bristol.h5265.Hotel-Information) Still don't see what you're looking for? [See all properties in Winsted.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F12%2F2025&endDate=15%2F12%2F2025®ionId=3000430645&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F12%2F2025&endDate=15%2F12%2F2025®ionId=3000430645&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F12%2F2025&endDate=15%2F12%2F2025®ionId=3000430645&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F12%2F2025&endDate=15%2F12%2F2025®ionId=3000430645&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F12%2F2025&endDate=15%2F12%2F2025®ionId=3000430645&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F12%2F2025&endDate=15%2F12%2F2025®ionId=3000430645&star=50&star=50&amenities=WATER_PARK) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. ## Learn more about Winsted Highland Lake offers refreshing swimming and boating during summer months, with a small beach perfect for families. Explore the American Museum of Tort Law founded by Ralph Nader, then grab coffee at one of Main Street's welcoming cafes. [See all hotels in Winsted](https://www.expedia.ca/Hotel-Search?startDate=2025-12-27&endDate=2025-12-28&adults=2®ionId=3000430645) ![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=400&h=400&p=1&q=high) Photo by Kim Knox Beckius ## Top Winsted Hotel Reviews ## Find out more about Winsted Luxury is the name of the game at the best 5 Stars hotels in Winsted. If you want to vacation like a true VIP, these are the places to go; from spacious resorts to boutique-inspired hot spots, the top Winsted 5 Stars hotels are dedicated to immersing you in the ultimate experience. Want to relax with a serene treatment at a designer spa? These properties offer them. Interested in tasting delicious dishes from top chefs? The gourmet restaurants at the 5 Stars Winsted hotels have you covered. You’ll even find first-class hotels near the city’s must-see attractions and most upscale entertainment districts. Plus, when you book your trip with Expedia.ca, you’ll get access to fantastic rates and seasonal discounts, so you can take advantage of a cheap deal on 5 Stars hotels Winsted without giving up even an inch of quality. Everything your heart desires (and a few perks designed to make it skip a beat): That’s what’s on offer when you plan a trip to the hotels with 5 Stars in Winsted. ## Frequently asked questions ### How much does it cost to stay in a 5-star hotel in Winsted? > - Search for the lowest price per night from CA $169 ### What makes a hotel 5 stars in Winsted? ### Are there any 5-star all-inclusive resorts in Winsted? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [3 Star Hotels in Northford ](https://www.expedia.ca/3Star-Northford-Hotels.s30-0-d6004524.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Windsor ](https://www.expedia.ca/3Star-Windsor-Hotels.s30-0-d7880.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Beacon Falls ](https://www.expedia.ca/4Star-Beacon-Falls-Hotels.s40-0-d6348182.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Coventry Lake ](https://www.expedia.ca/4Star-Coventry-Lake-Coventry-Hotels.s40-n553248635976474146-0.Travel-Guide-Filter-Hotels) - 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