Title: The Best 5 Star Hotels in Winchester, KY from $117 | Expedia.com [Winchester Travel Guide](https://expedia.com/Winchester.dx7876)[Hotels in Winchester](https://expedia.com/Winchester-Hotels.d7876.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.com/Winchester-Vacation-Rentals.d7876.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.com/Cheap-Flights-To-Winchester.d7876.Travel-Guide-Flights)[Car Rentals in Winchester](https://expedia.com/Car-Rentals-In-Winchester.d7876.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.com/Winchester.d7876.Destination-Travel-Guides) ![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Upfront pricing Our total price for your stay includes taxes and fees - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save 10% or more on over 100,000 hotels worldwide with Member Prices [Learn about One Key](https://www.expedia.com/welcome-one-key) - ![](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 [Feb 5 - Feb 6](https://www.expedia.com/Hotel-Search?regionId=7876&startDate=2026-02-05&endDate=2026-02-06&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 6 - Feb 7](https://www.expedia.com/Hotel-Search?regionId=7876&startDate=2026-02-06&endDate=2026-02-07&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 6 - Feb 8](https://www.expedia.com/Hotel-Search?regionId=7876&startDate=2026-02-06&endDate=2026-02-08&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 13 - Feb 15](https://www.expedia.com/Hotel-Search?regionId=7876&startDate=2026-02-13&endDate=2026-02-15&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ![](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.com/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.com/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. ![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 $194 nightly $225 total Mar 8 - Mar 9 Total with taxes and fees 9.4/10 Exceptional! (1,146 reviews) [](https://expedia.com/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 $101 nightly $117 total Feb 15 - Feb 16 Total with taxes and fees 9.4/10 Exceptional! (1,022 reviews) [](https://expedia.com/Lexington-Hotels-Elwood-Hotel-Suites.h2219782.Hotel-Information) ![21c Museum Hotel Lexington](https://images.trvl-media.com/lodging/13000000/12250000/12243800/12243775/7f6a345c_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### 21c Museum Hotel Lexington 167 West Main Street Lexington KY $173 nightly $201 total Mar 1 - Mar 2 Total with taxes and fees 8.8/10 Excellent! (1,002 reviews) [](https://expedia.com/Lexington-Hotels-21c-Museum-Hotel-Lexington.h12243775.Hotel-Information) Still don't see what you're looking for? [See all properties in Winchester.](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=2%2F6%2F2026&endDate=2%2F7%2F2026®ionId=7876&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=2%2F6%2F2026&endDate=2%2F7%2F2026®ionId=7876&star=50&star=50&amenities=POOL)[Spa](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=2%2F6%2F2026&endDate=2%2F7%2F2026®ionId=7876&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=2%2F6%2F2026&endDate=2%2F7%2F2026®ionId=7876&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=2%2F6%2F2026&endDate=2%2F7%2F2026®ionId=7876&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=2%2F6%2F2026&endDate=2%2F7%2F2026®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.com/Hotel-Search?startDate=2026-02-19&endDate=2026-02-20&adults=2®ionId=7876) ![Thanks to my friend of mine who's recommended me to this spot easy hike short walk to get there ](https://images.trvl-media.com/place/7876/9403688e-dbbb-4255-9528-8bddb2ed4db3.jpg?impolicy=fcrop&w=300&h=400&p=1&q=high) Photo by Nawa Aseen ## Top Winchester Hotel Reviews ## Find out more about Winchester Ready to experience the next standard in luxury? We know you're thinking about it. Add further luxury on your next trip to Winchester by treating yourself to the best of the best when it comes to accommodation. It's an ideal combination. There's no reason to delay a getaway to Winchester any longer. You'll join the multitudes of vacationers who have made Winchester so fashionable recently. We should also mention, the hotels in this area are known for guest services, so you know you'll want for nothing during your getaway. What are you waiting for? Book one of Expedia's luxurious 5-star hotels in Winchester and get ready to enjoy the getaway of a lifetime. ### 5-Star Hotels in Winchester Don't be afraid to live the high life while you're on vacation. Exceptional customer care, granite-tiled bathrooms, and rejuvenating spa offerings are waiting for you. You're sure to find exactly the accommodation you need. Besides that, you'll find that these hotels are kept in great shape and provide a fine place to lay your head at night. How do you want to relax? A mud wrap treatment that will leave you feeling outstanding? 24-hour room service, so you can order that filet mignon in the wee hours of the morning? A full-body massage to help your cares fall away? Don't want to take our word for it? Explore the review section and see what previous visitors have said. You're sure to find exactly what you're looking for! Yearning for experiences outside your hotel room? You're in luck. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. Whatever you plan to do, the 5-star hotels in Winchester are waiting for you to rest up after a busy day. ### Your Getaway Starts Today 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. It's time to indulge yourself -- Expedia can help you land a great deal on accommodation. Choose one of Expedia's Winchester 5-star hotels today and dive into in the lap of luxury tomorrow. ## Frequently asked questions ### How much does it cost to stay in a 5-star hotel in Winchester? > - Search for the lowest price per night from $117 ### What makes a hotel 5 stars in Winchester? ### Are there any 5-star all-inclusive resorts in Winchester? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Bluegrass Heritage Museum ](https://www.expedia.com/Bluegrass-Heritage-Museum-Hotels.0-l553248621561880736-0.Travel-Guide-Filter-Hotels) - [Hotels near Community Park ](https://www.expedia.com/Community-Park-Hotels.0-l6263168-0.Travel-Guide-Filter-Hotels) - [Hotels near Clark Regional Medical Center ](https://www.expedia.com/Clark-Regional-Medical-Center-Hotels.0-l6263150-0.Travel-Guide-Filter-Hotels) - [Hotels near Lykins Park ](https://www.expedia.com/Lykins-Park-Hotels.0-l6263146-0.Travel-Guide-Filter-Hotels) - [Hotels near Southwind Golf Course ](https://www.expedia.com/Southwind-Golf-Course-Hotels.0-l6263194-0.Travel-Guide-Filter-Hotels) - 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