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

Tonight
Aug 24 - Aug 25
Tomorrow
Aug 25 - Aug 26
This weekend
Aug 28 - Aug 30
Next weekend
Sep 4 - Sep 6

Our top choices for Middlesboro hotels with a bar

Aerial view
Front of property
Lounge
Property grounds

1. Woodlake Lodge Golf and Country Club

Woodlake Lodge Golf and Country Club
Tazewell
United States
James
NT$5,257
NT$5,901 total
includes taxes & fees
Aug 26 - Aug 27
Woodlake Lodge Golf and Country Club
Exterior
In-room safe, desk, laptop workspace, blackout drapes
Free daily continental breakfast
Lobby lounge

2. Quality Inn Harlan

Quality Inn Harlan
Harlan
United States
Gwen
NT$2,779
NT$3,152 total
includes taxes & fees
Sep 20 - Sep 21
Quality Inn Harlan
View all properties

Top Middlesboro Hotel Reviews

Holiday Inn Express Middlesboro by IHG

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."
frances, vincent hoskins (guest) 1-night trip
Posted 1 day 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 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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