Title: Book the Best Middlesboro LUXURY Hotels - Upscale Hotels in Middlesboro, KY | 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 luxury hotels in Middlesboro, KY ![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 Luxury Hotels Tonight [Sep 17 - Sep 18](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-09-17&endDate=2025-09-18&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 18 - Sep 19](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-09-18&endDate=2025-09-19&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Sep 19 - Sep 21](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-09-19&endDate=2025-09-21&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-09-26&endDate=2025-09-28&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Middlesboro Luxury Hotels ## Top Middlesboro Hotel Reviews ## Frequently asked questions ### Are you searching for a great accommodation for your luxury getaway to Middlesboro? > Amenities are important when you plan a trip, so we make it easy to get what you'd like to make your stay relaxing and comfortable. If you want an upscale hotel with fine dining, a spa, or several swimming pools, Expedia can help you find the best luxury hotel experience that Middlesboro has to offer. Middlesboro has some interesting things to see and do including Middlesboro Country Club and Middlesboro Mall, so you might want to take in the local sights during your visit. ### When can I expect good weather in Middlesboro? > Planning for the weather is an important factor for making your trip to Middlesboro 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 40°F. Average annual precipitation for Middlesboro is 62 inches. ### What's there to see and do in Middlesboro? > Experience Middlesboro with a stop at Middlesboro Country Club, Middlesboro Mall, and Cumberland Gap National Historical Park. 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