213 Middlesboro Vacation Rentals & Short Term Rentals

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Compare Middlesboro vacation rentals from 6 rental sites including HomeAway, Booking.com, Tripz and more, ranging from $33 to $775 a night.

Information about Middlesboro

Vacation Rentals in Middlesboro

Find the best Middlesboro vacation rentals with Tripping.com. Choose from 213 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $33 a night to $775 a night.

Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 147 of homes in Middlesboro offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 60 rentals with pool or jacuzzi, or relax with the family in one of the 176 homes with cable TV.

For all those dog lovers and cat lovers, Middlesboro offers 37 pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.

Search properties from 6 rental sites in Middlesboro where the top providers in that area are HomeAway, Booking.com, and Tripz. There are 163 HomeAway rentals, 22 Booking.com short term rentals and 13 Tripz vacation rentals.