An aerial view of a town surrounded by mountains, with a mix of residential and commercial buildings, and a highway running through the center.

Find Hotels with Bars in Middlesboro, KY

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Check availability on Middlesboro Hotels with Bars

Our top choices for Middlesboro hotels with a bar

Exterior

Quality Inn Harlan

Quality Inn Harlan
2.5 star property
Harlan
8.6 out of 10, Excellent, (371 reviews)
"A very clean room and helpful staff, who provided bottles of water when asked."
United States
Gwen
The price is AED 350
AED 397 total
includes taxes & fees
9 Aug - 10 Aug
Quality Inn Harlan
Aerial view

Woodlake Lodge Golf and Country Club

Woodlake Lodge Golf and Country Club
3.0 star property
Tazewell
9.2 out of 10, Wonderful, (150 reviews)
"Bar and dining options were very close. Bedding and towels were excellent."
United States
Karl
The price is AED 606
AED 680 total
includes taxes & fees
12 Jul - 13 Jul
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.
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Top Middlesboro Hotel Reviews

Holiday Inn Express Middlesboro by IHG

Holiday Inn Express Middlesboro by IHG

10/10 Excellent
"We checked in around 8pm and were greeted by the front desk staff was fantastic. They interacted with my 11-year-old great-niece in the best way. Sharing jokes and talking to her directly on her level. Of course, the adults felt comfortable and welcome as well. The pool was very nice and clean. The room was nice as well. We had no issues."
Donna 1-night trip
Posted 13 days ago
Holiday Inn Express Middlesboro by IHG

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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 11 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 Cumberland Gap National Historical Park and Middlesboro Country Club.
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 Cumberland Gap National Historical Park, The Pinnacle, and Pine Mountain State Resort Park, and then find a cozy spot for a nightcap. Other places to see include Middlesboro Country Club and Middlesboro Mall. 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.