Find the best Middlesboro vacation rentals on Tripping.com. With over 325 home rentals, take your pick from a wide variety of choices including studio apartments, luxury condos, and cozy cabin rentals. Prices in Middlesboro range from $29 a night. Many rentals can also be booked directly online.Vacation home rentals found on Tripping.com offer more amenities than the average hotel room along with many of the comforts of home. Going on a business trip or need to stay connected? 231 homes in Middlesboro offer high-speed WiFi Internet so you won’t miss a beat. Travelling with kids? Let them splash around in any of the 75 rentals with pool or jacuzzi, or relax with the family in one of the 245 homes with cable TV.For all those pet owners with dogs or cats, Middlesboro offers 47 pet-friendly vacation rentals for your extended family. Find the perfect vacation rental that matches your budget and style on Tripping.com.Search properties from 6 vacation rental sites in Middlesboro where the top providers in that area are HomeAway, Expedia, and TripAdvisor. There are 205 HomeAway rentals, 55 Expedia short term rentals and 33 TripAdvisor vacation rentals.