The Holiday Inn Express Middlesboro Hotel is located in Middlesboro's blend of historic woodlands, and mountain views. We are located close to Pine Mountain State Park and Cumberland Gap National Park. We are also close to the historic Cumberland Gap, the trail that was used by Daniel Boone, features 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 high speed WiFi and free Express Start breakfast. Our delicious Breakfast Bar served every morning includes meat, eggs, Cinnabon rolls, pancakes, fresh fruit, juices, cereals, breads/pastries, hardboiled eggs, and yogurt. Visit Middlesboro, KY and stay smart at the Holiday Inn Express Hotel.