Title: 5 Stars Hotels in Winchester, Lexington from CA $171 - Find Cheap Winchester Hotels With 5 Stars | Expedia.ca [Winchester Travel Guide](https://expedia.ca/Winchester.dx7876)[Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d7876.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d7876.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.ca/Cheap-Flights-To-Winchester.d7876.Travel-Guide-Flights)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d7876.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d7876.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/2d4532767bd47b707b21acca86317ffc.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Hyelsinta # 5 Stars Hotels in Winchester, Lexington from CA $171 ![](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 17 - Oct 18](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-10-17&endDate=2025-10-18&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 18 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-10-18&endDate=2025-10-19&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=7876&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=7876&startDate=2025-10-24&endDate=2025-10-26&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winchester 5 Star Hotels ![](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-d7876.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-d7876.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. ![DoubleTree Suites by Hilton Hotel Lexington](https://images.trvl-media.com/lodging/1000000/10000/9900/9900/f18d8c34_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### DoubleTree Suites by Hilton Hotel Lexington 2601 Richmond Rd, Lexington, KY CA $149 CA $173 total Nov 2 - Nov 3 includes taxes & fees 8.6/10 Excellent! (1,006 reviews) [](https://expedia.ca/Lexington-Hotels-DoubleTree-Suites-By-Hilton-Hotel-Lexington.h9900.Hotel-Information) ![The Manchester ](https://images.trvl-media.com/lodging/93000000/92440000/92430600/92430541/f02815a4_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Manchester 941 Manchester St, Lexington, KY CA $226 CA $287 total Nov 2 - Nov 3 includes taxes & fees 9.4/10 Exceptional! (1,008 reviews) [](https://expedia.ca/Lexington-Hotels-The-Manchester.h92430541.Hotel-Information) ![Elwood Hotel & Suites](https://images.trvl-media.com/lodging/3000000/2220000/2219800/2219782/f131bcc5_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Elwood Hotel & Suites 444 Parkway Drive, Lexington, KY CA $148 CA $171 total Oct 27 - Oct 28 includes taxes & fees 9.2/10 Wonderful! (1,013 reviews) [](https://expedia.ca/Lexington-Hotels-Elwood-Hotel-Suites.h2219782.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=18%2F10%2F2025&endDate=19%2F10%2F2025®ionId=7876&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=18%2F10%2F2025&endDate=19%2F10%2F2025®ionId=7876&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F10%2F2025&endDate=19%2F10%2F2025®ionId=7876&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F10%2F2025&endDate=19%2F10%2F2025®ionId=7876&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F10%2F2025&endDate=19%2F10%2F2025®ionId=7876&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F10%2F2025&endDate=19%2F10%2F2025®ionId=7876&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 Winchester Stroll through charming downtown streets lined with local shops and eateries. Tee off at Cassell Creek or Southwind Golf Course, then explore local history at the Bluegrass Heritage Museum. [See all hotels in Winchester](https://www.expedia.ca/Hotel-Search?startDate=2025-10-31&endDate=2025-11-01&adults=2®ionId=7876) ![](https://mediaim.expedia.com/destination/2/2d4532767bd47b707b21acca86317ffc.jpg?impolicy=fcrop&w=324&h=432&p=1&q=high) Photo by Hyelsinta ## Top Winchester Hotel Reviews ## Find out more about Winchester ## Five Star Hotels in Winchester There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Winchester so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Winchester and get ready to be pampered like never before. #### Get a Great Deal on 5-Star Hotels in Winchester Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places. Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town. #### Make Your Escape to Winchester The results are in, and Winchester 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Winchester! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Winchester today and settle down in the lap of luxury tomorrow. ## Frequently asked questions ### How much does it cost to stay in a 5-star hotel in Winchester? > You'll find various pricing options for 5-star hotels in Winchester on Expedia. The amount you pay will depend on your vacation dates, length of your trip and other factors. Compare all of the available properties for your desired dates and use our pricing and other filters to discover the ideal upscale stay. > > > > - Search for the lowest price per night from CA $171 ### What makes a hotel 5 stars in Winchester? > Exemplary guest service is the foundation of every 5-star hotel in Winchester. From the minute you arrive, staff attend to your every need, whether arranging valet parking or providing a turn-down service. Plus, hotels have to offer upscale amenities to be eligible for a 5-star rating. These can include luxury baths, on-site spa facilities, pools, gastronomic kitchens and knowledgeable concierge. ### Are there any 5-star all-inclusive resorts in Winchester? > Our handy filters are the quickest way to narrow down what you want. Select "5-star" and "All inclusive" to show the finest properties in Winchester where your meals, accommodations, entertainment and activities are included in the upfront price. 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