Travelers are voting Holiday Inn Express Harlen, Holiday Inn Exp Middlesboro and Sleep Inn And Suites Middlesbo as the best of 8 accommodations in Middlesboro. There are 121 accommodations in Williamsburg a city just 31 km from Middlesboro and 4 accommodations in Harlan which is 32 km distant. The most popular of these are Best Western Cozy House in Williamsburg and Holiday Inn Express Harlen in Harlan. You can find 670 accommodations in Kentucky and 51014 accommodations in the country of United States. Our members favorite in Kentucky is Days Inn Louisville Airport and Pelican Hill is the top pick in United States. Want more? Check out our map of accommodations in Middlesboro.