Photo by Alexis Wyrick

Middlesboro Holiday Rentals

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Holiday Rentals in Middlesboro

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Other types of properties in Middlesboro you may be interested in

Sleep Inn & Suites

2.5 star property
9.2 out of 10, Wonderful, (651)
"Huge room! Appreciated that hotel was quiet"
The price is S$130
includes taxes & fees
15 Dec - 16 Dec
Sleep Inn & Suites

Econo Lodge Middlesboro

2.0 star property
6.8 out of 10, (350)
"Decent hotel"
The price is S$124
includes taxes & fees
2 Dec - 3 Dec
Econo Lodge Middlesboro

Holiday Inn Express Williamsburg, an IHG Hotel

2.5 star property
9.0 out of 10, Wonderful, (867)
"Great place!!!"
The price is S$189
includes taxes & fees
1 Dec - 2 Dec
Holiday Inn Express Williamsburg, an IHG Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Are there holiday rentals in Middlesboro?

Yes, there are holiday rentals close to the most popular sights in Middlesboro, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the mountain landscape in Middlesboro. Make sure you have time to check out the churches while you're in the area.

What’s there to see and do in Middlesboro?

Cumberland Gap National Historical Park and Kentucky Ridge State Forest are a couple of scenic spots to enjoy the outdoors, whereas Bell County Historical Society Museum is one of the cultural attractions. While here, Middlesboro Mall and Middlesboro Country Club are other places worth a visit.

What’s a holiday rental in Middlesboro like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middlesboro. Holiday rentals feature amenities such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for families.