Title: Book the Best Hotels with BARS in Winchester in 2025 | 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 Hotels with Bar in Winchester, KY from CA $124 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 Hotels with Bar ## Top Winchester Hotels with Bar ![Suite, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/20000/16300/16227/eed31a13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/16300/16227/51af70a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/16300/16227/b2646625.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/16300/16227/93f7fc7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Winchester Winchester 9.2/10 Wonderful (441) "Close to Hwy which is nice. Staff friendly. " CA $164 CA $181 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Lexington-Hotels-Hampton-Inn-Winchester.h16227.Hotel-Information) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/15300/15247/8485fa77.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) ![Room amenity](https://images.trvl-media.com/lodging/1000000/20000/15300/15247/6f58ef98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Winchester Hotel Winchester 8.4/10 Very good (979) "Firm bed, clean room, friendly staff and adequate breakfast. " CA $112 CA $124 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=2025-10-16&endDate=2025-10-17®ionId=7876&adults=2&amenities=BAR&sort=RECOMMENDED&openPlayBack=true) ## Top Winchester Hotel Reviews ![Elwood Hotel & Suites](//images.trvl-media.com/lodging/3000000/2220000/2219800/2219782/f131bcc5_y.jpg) ### Elwood Hotel & Suites 10/10 Excellent "Clean room" [](https://expedia.ca/Lexington-Hotels-Elwood-Hotel-Suites.h2219782.Hotel-Information) ![Hilton Lexington/Downtown](//images.trvl-media.com/lodging/1000000/10000/2200/2101/b9ab6063_y.jpg) ### Hilton Lexington/Downtown 10/10 Excellent "Very nice! Definitely would stay there again" [](https://expedia.ca/Lexington-Hotels-Hilton-LexingtonDowntown.h2101.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 "Nice place. Very affordable and clean. " [](https://expedia.ca/Lexington-Hotels-Best-Western-Winchester-Hotel.h15247.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Lexington South / Hamburg](//images.trvl-media.com/lodging/1000000/290000/283200/283165/60f6cd78_y.jpg) ### La Quinta Inn & Suites by Wyndham Lexington South / Hamburg 10/10 Excellent "Nice clean room !" [](https://expedia.ca/Lexington-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Lexington-South-Hamburg.h283165.Hotel-Information) ![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 "We enjoyed our stay with Spark. Thank you." [](https://expedia.ca/Lexington-Hotels-Spark-By-Hilton-Lexington-Hamburg.h6639.Hotel-Information) ![Hyatt Regency Lexington](//images.trvl-media.com/lodging/1000000/10000/3500/3461/c0c49295_y.jpg) ### Hyatt Regency Lexington 10/10 Excellent "Courteous staff, clean, easy walking to a number of venues" [](https://expedia.ca/Lexington-Hotels-Hyatt-Regency-Lexington.h3461.Hotel-Information) ![Hyatt Place Lexington](//images.trvl-media.com/lodging/3000000/2060000/2057700/2057644/91e06cc9_y.jpg) ### Hyatt Place Lexington 10/10 Excellent "Wonderful room. Comfortable bed." [](https://expedia.ca/Lexington-Hotels-Hyatt-Place-Lexington.h2057644.Hotel-Information) ![Natural Bridge State Resort Park](//images.trvl-media.com/lodging/16000000/15440000/15437800/15437778/df7a7684_y.jpg) ### Natural Bridge State Resort Park 10/10 Excellent "A wonderful lodge within a gorgeous state park! Excellent food, two restaurants onsite" [](https://expedia.ca/Slade-Hotels-Natural-Bridge-State-Resort-Park.h15437778.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 "I loved the costumer service. the cooks, servers and bar tenders are efficient, friendly, work as a team. amazing costumer service. I loved the breakfast bar with option for cooking special items like ommeletes, avocado toast, other. nice surprise to find happy hour option. I will definatly come back" [](https://expedia.ca/Lexington-Hotels-Embassy-Suites-By-Hilton-LexingtonUK-Coldstream.h203587.Hotel-Information) ## Frequently asked questions ### Searching for hotels with bars in Winchester? > Winchester features 20 properties to choose from, and likely many will have a bar where you can enjoy drink after a day of exploring. While you're here, consider a visit to Bluegrass Heritage Museum and Lykins Park. ### What are the best hotels with bars in Winchester? > Here are a few of the top hotels with bars in and around Winchester: [Best Western Winchester Hotel](https://www.expedia.ca/Lexington-Hotels-Best-Western-Winchester-Hotel.h15247.Hotel-Information): Hotel with 2 restaurants. Enjoy the bar, breakfast, and free airport shuttle. [GLō Best Western Lexington](https://www.expedia.ca/Lexington-Hotels-GLo-Best-Western-Lexington.h123895.Hotel-Information): Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. [Hilton Lexington/Downtown](https://www.expedia.ca/Lexington-Hotels-Hilton-LexingtonDowntown.h2101.Hotel-Information): Hotel with restaurant. Enjoy the bar, free breakfast, and WiFi. [GuestHouse Lexington](https://www.expedia.ca/Lexington-Hotels-GuestHouse-Lexington.h426325.Hotel-Information): Hotel with 2 restaurants. Enjoy the 2 bars, free WiFi, and breakfast. [Hyatt Regency Lexington](https://www.expedia.ca/Lexington-Hotels-Hyatt-Regency-Lexington.h3461.Hotel-Information): Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. ### What is there to do in Winchester? > To experience the area's highlights, consider visiting Fort Boonesborough State Park, Hamburg Pavilon, and Raven Run Nature Sanctuary, and then find a cozy spot for a nightcap. Other places to see include Bluegrass Heritage Museum and Lykins Park. Winchester is known for its restaurants. ### When is the best time to visit Winchester? > Visiting local bars in Winchester is more fun in good weather. These rainfall averages and temperatures can help you choose the best time for bar hopping. 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. ### How can I get to Winchester and around the area? > You might want to make the most of these transportation choices in and around Winchester: Fly into Blue Grass Airport (LEX), which is located 23 mi (37.1 km) away from the heart of the city. 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