The Best Hotels with Bars in Middlesboro, KY from AED 363 in 2026

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

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Our top choices for Middlesboro hotels with a bar

1. Woodlake Lodge Golf and Country Club

Tazewell

James

AED 606

AED 680 total

includes taxes & fees

25 Aug - 26 Aug

In-room safe, desk, laptop workspace, blackout drapes

2. Quality Inn Harlan

Harlan

Gwen

AED 320

AED 363 total

includes taxes & fees

20 Sep - 21 Sep

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Top Middlesboro Hotel Reviews

Holiday Inn Express Middlesboro by IHG

10/10 Excellent

"This is my absolute favorite place to stay on my route from Ohio to East Tennessee and back.. the staff is very friendly the hotel is always clean breakfast is wonderful and I'm picky.. I used to manage nights in hotels so I have experience in the hospitality industry and I absolutely love this location."

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 Mall.

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 Mall and Kentucky Ridge State Forest. 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.

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