Travelers are voting Cumberland Gap Natl Hist Park / Wilderness Road, Best Western Wilderness Trail and Holiday Inn Express Harlen 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 Americas Best Value Inn in Williamsburg and Settle Inn And Suites Harlan in Harlan. You can find 670 accommodations in Kentucky and 51013 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.