Title: Book the Best Hotels with BARS in Middlesboro in 2025 | Expedia.ca [Hotels in Middlesboro](https://expedia.ca/Middlesboro-Hotels.d8853.Travel-Guide-Hotels)[Vacation Rentals in Middlesboro](https://expedia.ca/Middlesboro-Vacation-Rentals.d8853.Travel-Guide-VacationRentals)[Flights to Middlesboro](https://expedia.ca/Cheap-Flights-To-Middlesboro.d8853.Travel-Guide-Flights)[Middlesboro Car Rentals](https://expedia.ca/Car-Rentals-In-Middlesboro.d8853.Car-Rental-Guide)[Middlesboro Vacation Packages](https://expedia.ca/Middlesboro.d8853.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/aaf95e2362319d0be23171c8a72261cf.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Alexis Wyrick # Find Hotels with Bar in Middlesboro, KY from CA $155 ![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 Middlesboro Hotels with Bar ## Top Middlesboro Hotels with Bar ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/17000/16941/b003bff0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/20000/17000/16941/0451853f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/17000/16941/94a0b136.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/20000/17000/16941/43d53c9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Harlan 8.6/10 Excellent (322) "Wonderful stay and amenities " CA $137 CA $155 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Harlan-Hotels-Quality-Inn.h16941.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/17000000/16540000/16536400/16536329/544d1b99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/17000000/16540000/16536400/16536329/55fb9b6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, free WiFi](https://images.trvl-media.com/lodging/17000000/16540000/16536400/16536329/b0b265ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/17000000/16540000/16536400/16536329/fed88dd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Woodlake Lodge Golf and Country Club Tazewell 9.4/10 Exceptional (141) "Gym was closed, restaurant was closed... pool was nice. Course is beautiful." CA $202 CA $227 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Morristown-Hotels-Woodlake-Lodge-Golf-And-Country-Club.h16536329.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=2025-10-23&endDate=2025-10-24®ionId=8853&adults=2&amenities=BAR&sort=RECOMMENDED&openPlayBack=true) ## Top Middlesboro Hotel Reviews ![Holiday Inn Express Middlesboro by IHG](//images.trvl-media.com/lodging/1000000/70000/60900/60850/3963de73_y.jpg) ### Holiday Inn Express Middlesboro by IHG 10/10 Excellent "Clean room Great breakfast Staff friendly and helpful " [](https://expedia.ca/Middlesboro-Hotels-Holiday-Inn-Express-Middlesboro.h60850.Hotel-Information) ## Frequently asked questions ### Searching for hotels with bars in Middlesboro? > Though you might not find a hotel in Middlesboro well-known for its bar, you will find 10 properties to choose from, some of which will have an onsite bar where you can unwind with a late-night cocktail after a day out and about. While you're here, consider a visit to Middlesboro Country Club and Middlesboro Mall. ### What are the best hotels with bars in Middlesboro? > Below is a favorite hotel in the area: [Sleep Inn & Suites](https://www.expedia.ca/Middlesboro-Hotels-Sleep-Inn-Suites.h3929546.Hotel-Information): Hotel with restaurant. Enjoy the bar, free breakfast, and free WiFi. ### What is there to do in Middlesboro? > To experience the area's highlights, consider visiting Middlesboro Country Club, Middlesboro Mall, and Cumberland Gap National Historical Park, and then find a cozy spot for a nightcap. Other places to see include Kentucky Ridge State Forest and Bell County Historical Society Museum. Middlesboro is appreciated for its mountain landscape. ### When is the best time to visit Middlesboro? > Visiting local bars in Middlesboro is more fun in good weather. These temperatures and rainfall averages 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 40°F. 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