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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Middlesboro holiday rentals

A covered outdoor deck with wooden flooring and metal chairs.

1. Peaceful & Private! Pet-friendly Williamsburg Home

Peaceful & Private! Pet-friendly Williamsburg Home
3.0 star property
Williamsburg
The price is 3.216.654 ₫
7.849.402 ₫ total
includes taxes & fees
12 Nov - 13 Nov
Peaceful & Private! Pet-friendly Williamsburg Home
A wooden cabin with a porch, a door, a window with a view of the outdoors, and a small table with a potted plant.

2. Studio 8 Mi to Norris Lake! Couples & Pets Welcome

Studio 8 Mi to Norris Lake! Couples & Pets Welcome
3.0 star property
Tazewell
The price is 3.063.480 ₫
6.243.117 ₫ total
includes taxes & fees
12 Nov - 13 Nov
Studio 8 Mi to Norris Lake! Couples & Pets Welcome
A spacious living room with wooden beams, leather sofas, a wooden coffee table, and a mounted deer head.

3. Peaceful Mountain Cabin w/ Views in Williamsburg

Peaceful Mountain Cabin w/ Views in Williamsburg
2.0 star property
Williamsburg
2.0 out of 10, (1 review)
"The owners were very polite. The only issue I had was that the listing online did not say anything about it being fully solar powered with no electricity. We left in the middle of the night the first night because there was no power at all."
United States
Chandler
The price is 3.216.654 ₫
8.709.984 ₫ total
includes taxes & fees
15 Nov - 16 Nov
Peaceful Mountain Cabin w/ Views in Williamsburg
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.
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Find holiday rentals that suit your style

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Top Middlesboro Hotel Reviews

A hotel room with a sofa, a coffee table, a bed with a canopy, a TV, and artwork on the walls.
Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro
Middlesboro

10/10 Excellent

Clean and great service
United Kingdom
Lar
Reviewed May 16, 2025
Sleep Inn & Suites Middlesboro

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.

How many holiday rentals are there in Middlesboro?

With 6 Expedia holiday rentals, you're guaranteed to find just the right place for your Middlesboro stay.

What’s there to see and do in Middlesboro?

Cultural attractions include Bell County Historical Society Museum, whereas Kentucky Ridge State Forest is a spot to enjoy nature. While here, Middlesboro Mall and Cumberland Gap National Historical Park 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.