Title: Book the Best Winchester LUXURY Hotels - Upscale Hotels in Winchester, KY | Expedia.ca [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)[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 # Find luxury hotels in Winchester, KY ![](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 Luxury Hotels Tonight [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-10-15&endDate=2025-10-16&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 16 - Oct 17](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-10-16&endDate=2025-10-17&adults=2&propertyStyle=LUXURY&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&propertyStyle=LUXURY&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&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winchester Luxury Hotels ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/20000/15300/15247/690f0ff1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/15300/15247/2ea0f039.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/15300/15247/8485fa77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/15300/15247/80f943aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Winchester Hotel Winchester 8.4/10 Very good (983) "Firm bed, clean room, friendly staff and adequate breakfast. " CA $113 CA $125 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Lexington-Hotels-Best-Western-Winchester-Hotel.h15247.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-29&endDate=2025-10-30®ionId=7876&adults=2&star=50&sort=RECOMMENDED&openPlayBack=true) ## Top Winchester Hotel Reviews ![Spark by Hilton Lexington Hamburg](//images.trvl-media.com/lodging/1000000/10000/6700/6639/4dbc3493_y.jpg) ### Spark by Hilton Lexington Hamburg 10/10 Excellent "The hotel was in a very convenient location & close to lots of attractions. " [](https://expedia.ca/Lexington-Hotels-Spark-By-Hilton-Lexington-Hamburg.h6639.Hotel-Information) ![Embassy Suites by Hilton Lexington/UK Coldstream](//images.trvl-media.com/lodging/1000000/210000/203600/203587/32ffb492_y.jpg) ### Embassy Suites by Hilton Lexington/UK Coldstream 10/10 Excellent "Beautiful surroundings " [](https://expedia.ca/Lexington-Hotels-Embassy-Suites-By-Hilton-LexingtonUK-Coldstream.h203587.Hotel-Information) ![Elwood Hotel & Suites](//images.trvl-media.com/lodging/3000000/2220000/2219800/2219782/f131bcc5_y.jpg) ### Elwood Hotel & Suites 10/10 Excellent "Great stay!" [](https://expedia.ca/Lexington-Hotels-Elwood-Hotel-Suites.h2219782.Hotel-Information) ![Motel 6 Lexington, KY - East I-75](//images.trvl-media.com/lodging/2000000/1040000/1039800/1039703/c1f9e9cf_y.jpg) ### Motel 6 Lexington, KY - East I-75 10/10 Excellent "Thanks for your service " [](https://expedia.ca/Lexington-Hotels-Motel-6-Lexington.h1039703.Hotel-Information) ![GuestHouse Lexington](//images.trvl-media.com/lodging/1000000/430000/426400/426325/18dc9903_y.jpg) ### GuestHouse Lexington 10/10 Excellent "Clean room! Everything great! TV practically knew! Wi-Fi superb! A great bargain! Excellent, hot breakfast! I love the location!" [](https://expedia.ca/Lexington-Hotels-GuestHouse-Lexington.h426325.Hotel-Information) ![Days Inn Lexington SE/Hamburg](//images.trvl-media.com/lodging/1000000/10000/9600/9539/685edbce_y.jpg) ### Days Inn Lexington SE/Hamburg 10/10 Excellent "Good" [](https://expedia.ca/Lexington-Hotels-Days-Inn-By-Wyndham-Lexington-Southeast.h9539.Hotel-Information) ![DoubleTree Suites by Hilton Hotel Lexington](//images.trvl-media.com/lodging/1000000/10000/9900/9900/f18d8c34_y.jpg) ### DoubleTree Suites by Hilton Hotel Lexington 10/10 Excellent "Staff was friendly and informative!" [](https://expedia.ca/Lexington-Hotels-DoubleTree-Suites-By-Hilton-Hotel-Lexington.h9900.Hotel-Information) ![Best Western Winchester Hotel](//images.trvl-media.com/lodging/1000000/20000/15300/15247/690f0ff1_y.jpg) ### Best Western Winchester Hotel 10/10 Excellent "Great value for price. Good location off interstate. Good breakfast. Everything was very clean. Friendly night clerk checked us in. " [](https://expedia.ca/Lexington-Hotels-Best-Western-Winchester-Hotel.h15247.Hotel-Information) ![Hyatt Place Lexington](//images.trvl-media.com/lodging/3000000/2060000/2057700/2057644/91e06cc9_y.jpg) ### Hyatt Place Lexington 10/10 Excellent "Everything was great" [](https://expedia.ca/Lexington-Hotels-Hyatt-Place-Lexington.h2057644.Hotel-Information) ## Frequently asked questions ### Are you searching for a great accommodation for your luxury trip to Winchester? > Use Expedia to help you arrange a flight to Blue Grass Airport (LEX) airport, and then choose from a variety of places to stay that will deliver the luxury you want. Amenities are important when you plan a trip, so we make it easy to find what you want to make your stay special. If you want an upscale hotel with a spa, an indoor pool, or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Winchester offers. During your visit, you might want to enjoy the restaurants which Winchester is known for. ### When can I expect good weather in Winchester? > Planning for the weather is an important factor for making your trip to Winchester a success, especially when you're splurging. The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Winchester is 56 inches. ### What's there to see and do in Winchester? > Experience Winchester and visit Bluegrass Heritage Museum, Lykins Park, and Southwind Golf Course. 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