Photo by Alexis Wyrick

Find Hotels with Bars in Middlesboro, KY

Start date: Check-in selected.
To Date
End date: Check-out

Check availability on Middlesboro Hotels with Bars

Top Middlesboro Hotels with Bars

Exterior
Quality Inn

Quality Inn

2.5 star property
Harlan
8.6 out of 10, Excellent, (335)
"Room was nice and clean, staff very courteous, breakfast very good."
United States
Gary
$89 nightly
The price is $101
Jan 4 - Jan 5, 2026
Total with taxes and fees
Quality Inn
Aerial view
Woodlake Lodge Golf and Country Club

Woodlake Lodge Golf and Country Club

3.0 star property
Tazewell
9.4 out of 10, Exceptional, (142)
"Gym was closed, restaurant was closed... pool was nice. Course is beautiful."
United States
Daniel
$130 nightly
The price is $146
Jan 1 - Jan 2, 2026
Total with taxes and fees
Woodlake Lodge Golf and Country Club
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.
View all properties

Top Middlesboro Hotel Reviews

Holiday Inn Express Middlesboro by IHG

Holiday Inn Express Middlesboro by IHG

10/10 Excellent
"Very comfortable and clean."
Lisa 2-night trip
Posted 1 month ago
Holiday Inn Express Middlesboro by IHG

Frequently asked questions

Searching for hotels with bars in Middlesboro?
Though you might not find a hotel in Middlesboro well-known for its bar, you will find 10 properties to choose from, some of which will have an onsite bar where you can unwind with a late-night cocktail after a day out and about. While you're here, consider a visit to Middlesboro Mall and Cumberland Gap National Historical Park.
What are the best hotels with bars in Middlesboro?
Below is a favorite hotel in the area: Sleep Inn & Suites Middlesboro: Hotel with restaurant. Enjoy the bar, free breakfast, and free WiFi.
What is there to do in Middlesboro?
To experience the area's highlights, consider visiting Middlesboro Mall, Cumberland Gap National Historical Park, and The Pinnacle, and then find a cozy spot for a nightcap. Other places to see include Bell County Historical Society Museum and Middlesboro Country Club. Middlesboro is appreciated for its mountain landscape.
When is the best time to visit Middlesboro?
Visiting local bars in Middlesboro is more fun in good weather. These temperatures and rainfall averages can help you choose the best time for bar hopping. The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 40°F. Average annual precipitation for Middlesboro is 62 inches.

Explore a world of travel with Expedia