Title: 5 Stars Hotels in Winchester, Winsted from CA $241 - Find Cheap Winchester Hotels With 5 Stars | Expedia.ca [Winchester Travel Guide](https://expedia.ca/Winchester.dx553248635975869849)[Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d553248635975869849.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d553248635975869849.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.ca/Cheap-Flights-To-Winchester.d553248635975869849.Travel-Guide-Flights)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d553248635975869849.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d553248635975869849.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 5 Stars Hotels in Winchester, Winsted from CA $241 - ![](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 Winchester 5 Star Hotels Tonight [Nov 4 - Nov 5](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-11-04&endDate=2025-11-05&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 5 - Nov 6](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-11-05&endDate=2025-11-06&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-11-07&endDate=2025-11-09&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-11-14&endDate=2025-11-16&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winchester 5 Star Hotels ![Couples treatment rooms, steam room, body treatments, aromatherapy](https://images.trvl-media.com/lodging/1000000/180000/170800/170742/5296f0bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/1000000/180000/170800/170742/ff95995c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/180000/170800/170742/a6c73ef6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily cooked-to-order breakfast for a fee](https://images.trvl-media.com/lodging/1000000/180000/170800/170742/afc72d8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mayflower Inn & Spa, Auberge Collection Washington 9.2/10 Wonderful (54) "We had bugs crawling all over our room and we were unable to be relocated according to hotel staff it was disgusting" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) stacy CA $1,201 CA $1,446 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Torrington-Hotels-Mayflower-Inn-Spa.h170742.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/22000000/21770000/21767700/21767645/4a6d4a2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Bedrooms](https://images.trvl-media.com/lodging/22000000/21770000/21767700/21767645/55d845bc.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) ![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) ### Troutbeck 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) ![Fireplace](https://images.trvl-media.com/lodging/71000000/70550000/70549400/70549365/0802bc3c.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) ![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) ### Las Flores Villa 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-Winchester-Hotels.s50-0-d553248635975869849.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Winchester-Hotels.s50-0-d553248635975869849.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 Winchester. ![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 $437 CA $524 total Nov 23 - Nov 24 includes taxes & fees 9.6/10 Exceptional! (1,002 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 $209 CA $241 total Nov 24 - Nov 25 includes taxes & fees 9/10 Wonderful! (1,001 reviews) [](https://expedia.ca/Hartford-Hotels-DoubleTree-By-Hilton-Hotel-Bristol.h5265.Hotel-Information) ![The Litchfield Inn](https://images.trvl-media.com/lodging/5000000/4980000/4978900/4978856/9aa3fa98_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Litchfield Inn 432 Bantam Road, Litchfield, CT CA $386 CA $444 total Nov 6 - Nov 7 includes taxes & fees 9/10 Wonderful! (949 reviews) [](https://expedia.ca/Torrington-Hotels-The-Litchfield-Inn.h4978856.Hotel-Information) Still don't see what you're looking for? [See all properties in Winchester.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=06%2F11%2F2025&endDate=07%2F11%2F2025®ionId=553248635975869849&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=06%2F11%2F2025&endDate=07%2F11%2F2025®ionId=553248635975869849&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=06%2F11%2F2025&endDate=07%2F11%2F2025®ionId=553248635975869849&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=06%2F11%2F2025&endDate=07%2F11%2F2025®ionId=553248635975869849&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=06%2F11%2F2025&endDate=07%2F11%2F2025®ionId=553248635975869849&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=06%2F11%2F2025&endDate=07%2F11%2F2025®ionId=553248635975869849&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. ## Top Winchester Hotel Reviews ## Find out more about Winchester Luxury is the name of the game at the best 5 Stars hotels in Winchester. 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 Winchester 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 Winchester 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 Winchester without giving up even an inch of quality. 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