Stay at One of the Best Hotels in Middlesboro, KY Located just off US-25 in the beautiful, historic woodlands of Kentucky, the Holiday Inn Express Middlesboro hotel is waiting to welcome you with warm, Southern hospitality. Whether you're visiting for business or leisure, you'll enjoy great amenities with a free breakfast and free high-speed Internet access. For corporate guests, companies such as Lincoln Memorial University and Middlesboro Hospital are minutes from us in Middlesboro, Kentucky. Our hotel's guests can reserve our event facilities, which have 1,300 sq ft of flexible space and can accommodate up to 50 people. In addition, we have copy and fax services, as well as free high-speed Internet access. Visiting and hiking the famous Cumberland Gap is a favorite activity of our hotel's guests. While in Middlesboro, KY, families can explore the gorgeous Pine Mountain State Park. Visit LMU and learn more about a great president at Abraham Lincoln Museum. Golf enthusiasts may wish to reserve a tee time at one of the oldest courses in the country, Middlesboro Country Club. When you stay with us in Middlesboro, Kentucky, our hotel's staff invites you to enjoy the complimentary, hot Express Start Breakfast Bar, which features our delicious cinnamon rolls and 100% Arabica bean coffee. We also have a seasonal, outdoor pool that kids love! Book your room today to experience top-notch quality at a great price at our Middlesboro hotel!