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 Adventure Hotels in Middlesboro, KY

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Check availability on Middlesboro Adventure Hotels

Tonight
Sep 21 - Sep 22
Tomorrow
Sep 22 - Sep 23
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Our top choices for Middlesboro adventure hotels

1. Pine Mountain State Resort Park

Pine Mountain State Resort Park
Pineville
United States
James
NT$3,054
NT$3,366 total
includes taxes & fees
Sep 22 - Sep 23
Pine Mountain State Resort Park

2. Holiday Inn Express Williamsburg by IHG

Holiday Inn Express Williamsburg by IHG
Williamsburg
United States
Christy
NT$3,628
NT$4,038 total
includes taxes & fees
Sep 27 - Sep 28
Holiday Inn Express Williamsburg by IHG

3. Peaceful Mountain Cabin w/ Views in Williamsburg

Peaceful Mountain Cabin w/ Views in Williamsburg
Williamsburg
United States
Chandler
NT$4,010
NT$10,858 total
includes taxes & fees
Sep 22 - Sep 23
Peaceful Mountain Cabin w/ Views in Williamsburg
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Top Middlesboro Hotel Reviews

Holiday Inn Express Middlesboro by IHG

Holiday Inn Express Middlesboro by IHG

10/10 Excellent
"We had a wonderful stay at the Holiday Inn Express in Middlesboro, KY. The staff truly made our visit special—they were incredibly pleasant, helpful, and always made sure all of our needs were met. Every single day, we were greeted with warm smiles and friendly faces. They even went out of their way to give us excellent local recommendations for dinner. Their outstanding customer service made us feel right at home. We highly recommend this hotel to anyone visiting the area!"
Tolly 5-night trip
Posted 5 days ago
Holiday Inn Express Middlesboro by IHG
Pine Mountain State Resort Park

Pine Mountain State Resort Park

8/10 Good
"Hello The room was clean the balcony was awesome. Needed to have a small frig in the room that was disappointing, and the children running on the second floor was challenging at 6 am. but other than that we enjoyed out stay The pool was excellent."
Mary 2-night trip
Posted 7 days ago
Pine Mountain State Resort Park

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