1. USA
  2. Kentucky
  3. Middlesboro
  4. Summer Rental

Middlesboro Summer Rentals, Cottages & Cabins

Book a Place to Stay in Middlesboro for Your Summer Getaway

About Middlesboro Summer Rental on PickleTrip

PickleTrip™'s summer rentals in Middlesboro are perfect for your next summer getaway. We offer a wide range of properties to choose from, including homes with top-notch pickleball courts or nearby facilities, private pools, indoor/outdoor pools, hot tubs, WiFi, beach access, and more. Whether you're traveling with family, friends, or a group, we have a rental that will suit your needs.

Enjoy the perfect summer vacation in Middlesboro with PickleTrip™. Our summer rental homes are designed to provide you with maximum comfort and relaxation. Choose from a variety of properties, including condos, resorts, villas, bungalows, cozy cabins, RVs, and cottages. Stay and play pickleball when you travel with PickleTrip™.

Show more
Show less

Frequently Asked Questions About Middlesboro Luxury Rentals

In 2025, PickleTrip offers 18 summer rentals in or around Middlesboro. Find unique home rentals for your summer holiday or a weekend getaway with family and friends.
The average price per night for a summer rental in Middlesboro is $214. Check the full list of summer accommodations in Middlesboro.
There are 18 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with PickleTrip.

Yes, here are some popular summer holiday rentals in Middlesboro that have a private or indoor pool:

Check all holiday rentals with a pool in Middlesboro on PickleTrip.

Yes, We have 18 summer rental homes in Middlesboro and types of place to stay in Middlesboro include:

  • Vacation Homes: 18 available for rent
  • Villas: 18 Rentals available for rent
  • Holiday Apartments: 18 Rentals available for rent
  • Hotels with Suites: 18 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Middlesboro. Use our search filter to discover all of our luxury summer accommodations with an indoor/outdoor pool. Sorting by price is another way to find the most and least expensive luxury summer rentals in Middlesboro.