Title: 5 Stars Hotels in Winchester, Winsted from CA $287 - 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 $287 ![](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 [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-10-13&endDate=2025-10-14&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-10-14&endDate=2025-10-15&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-10-17&endDate=2025-10-19&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-10-24&endDate=2025-10-26&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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/1000000/180000/170800/170742/a6c73ef6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/180000/170800/170742/8d38e888.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mayflower Inn & Spa, Auberge Collection Washington 9.2/10 Wonderful (53) "Incredible place - will definitely return. " CA $1,247 CA $1,499 total includes taxes & fees Nov 4 - Nov 5 [](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) ![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) ![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) ### 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) ![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) ![Family House | Terrace/patio](https://images.trvl-media.com/lodging/71000000/70550000/70549400/70549365/3527e7ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Las Flores Villa New Preston 10/10 Exceptional (1) CA $1,424 CA $2,198 total includes taxes & fees Oct 15 - Oct 16 [](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 $435 CA $522 total Nov 2 - Nov 3 includes taxes & fees 9.6/10 Exceptional! (1,003 reviews) [](https://expedia.ca/Hartford-Hotels-Delamar-West-Hartford.h18166744.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 $398 CA $458 total Nov 3 - Nov 4 includes taxes & fees 9/10 Wonderful! (946 reviews) [](https://expedia.ca/Torrington-Hotels-The-Litchfield-Inn.h4978856.Hotel-Information) ![Simsbury 1820 House](https://images.trvl-media.com/lodging/1000000/50000/42300/42279/6326a611_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Simsbury 1820 House 731 Hopmeadow St, Simsbury, CT CA $229 CA $287 total Nov 2 - Nov 3 includes taxes & fees 9.2/10 Wonderful! (998 reviews) [](https://expedia.ca/Hartford-Hotels-Simsbury-1820-House.h42279.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=14%2F10%2F2025&endDate=15%2F10%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=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=553248635975869849&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=553248635975869849&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=553248635975869849&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=553248635975869849&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%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 ![Mayflower Inn & Spa, Auberge Collection](//images.trvl-media.com/lodging/1000000/180000/170800/170742/5296f0bf_y.jpg) ### Mayflower Inn & Spa, Auberge Collection 2/10 Terrible "We had bugs crawling all over our room and we were unable to be relocated according to hotel staff it was disgusting" [](https://expedia.ca/Torrington-Hotels-Mayflower-Inn-Spa.h170742.Hotel-Information) ## 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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