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 de ...