The Best Hotels with a Pool in Middlesboro, KY from SAR 319 in 2025

Q: What are some accommodations with pools in Middlesboro?

Sleep Inn & Suites : Offers continental, a seasonal outdoor pool, and free self parking. Econo Lodge Middlesboro : Provides daily, an indoor pool, and free self parking. Holiday Inn Express Williamsburg by IHG : Features a full-service spa, a seasonal outdoor pool, and daily. Days Inn by Wyndham Jellico - Tennessee State Line : Provides kitchens, a communal pool, and Smart TVs. Fabulous view, walking distance from Flat Hollow Marina : Offers complimentary wireless internet access, a communal pool, and kitchens.

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"Excellent hotel "

SAR 492 total

includes taxes & fees

18 Feb - 19 Feb

"I was disappointed that it said breakfast included but it was only a continental breakfast. Other than that our room was clean and the beds were so comfortable. Staff very friendly "

SAR 352 total

includes taxes & fees

23 Feb - 24 Feb

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Recent reviews of Middlesboro hotels

5/5 Excellent

"Rooms are always very clean the people at the desk are always nice love staying here!!"

A verified traveler stayed at Econo Lodge Middlesboro

Posted 8 days ago

Days Inn by Wyndham Jellico - Tennessee State Line

5/5 Excellent

"This is an older property with some nice 1960s charm. I promise, it has been renovated. It’s clean and set back from the highway, among a few other hotels. I could walk to a convenience store. The office is up front in a separate building. They honored my request for a first floor room. As a woman traveling alone I felt safe here. Thank you"

A verified traveler stayed at Days Inn by Wyndham Jellico - Tennessee State Line

Posted 2 months ago

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Frequently asked questions

What are some accommodations with pools in Middlesboro?

Sleep Inn & Suites: Offers continental, a seasonal outdoor pool, and free self parking. Econo Lodge Middlesboro: Provides daily, an indoor pool, and free self parking. Holiday Inn Express Williamsburg by IHG: Features a full-service spa, a seasonal outdoor pool, and daily. Days Inn by Wyndham Jellico - Tennessee State Line: Provides kitchens, a communal pool, and Smart TVs. Fabulous view, walking distance from Flat Hollow Marina: Offers complimentary wireless internet access, a communal pool, and kitchens.

What is there to see and do in Middlesboro?

Spend some time experiencing the great outdoors at Cumberland Gap National Historical Park and Kentucky Ridge State Forest. During your stay, check out sights such as Middlesboro Mall, Middlesboro Country Club, and Bell County Historical Society Museum. Take in the natural beauty of Middlesboro with the mountain views.

When is the best time to book a hotel with a pool in Middlesboro?

You may want to consider a place to stay that offers an outdoor pool if you plan to visit Middlesboro in the warmest months of July, August, or June when the average temp is 72°F. Lodging with an indoor pool may be the way to go if you visit during the coldest months of January, February, or December when the average temperature is 40°F.

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