The Holiday Inn Express Middlesboro Hotel is located in Middlesboro's blend of historic woodlands, wonderful views, and well-seasoned beauty. We are located next to one of the oldest State Parks - Pine Mountain State Park and Cumberland Gap National Park. The Holiday Inn Express is not far from Cumberland Gap, the trail that was used by Daniel Boone, features a lot of hiking trails, crafts and Southern Hospitality. The Holiday Inn Express is located in an area where the dining is the choosing, whether you desire the charm of a historic view or the economy of a family restaurant, you can find it here. Hotel features include free local phone calls and a complimentary Express Start continental breakfast. Enjoy a unique breakfast experience at our new Express Start Breakfast Bar served every morning featuring a selection of fruits, juices, cereals, breads/pastries, and even hardboiled eggs. We have also created the world's best tasting cinnamon roll. Visit Middlesboro, KY and stay smart at the Holiday Inn Express Hotel.