The Best Hotels with a Pool in Middlesboro, KY from SAR 337 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, an IHG Hotel : Features a full-service spa, a seasonal outdoor pool, and daily. Days Inn by Wyndham Jellico - Tennessee State Line : Features complimentary wireless internet access, a communal pool, and kitchens. Dog-friendly lakefront house with hot tub, central AC, & mountain view : Offers kitchens, a communal pool, and Smart TVs.

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"Excellent hotel "

"Great cozy rooms..pillows suck"

SAR 372 total

includes taxes & fees

9 Feb - 10 Feb

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Recent reviews of Middlesboro hotels

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 1 month ago

5/5 Excellent

"Elevator to upper floors was nice esp if you have lots of luggage or are unable to do stairs. Bed was very comfortable, hot water was hot and for a decent shower, room was very clean and updated. 2 places to eat-Mexican Food and Drive in that were easy to walk to. Continental breakfast was very accommodating. It was a very nice place to stay. Will definitely stay again if I am in the area. "

A verified traveler stayed at Econo Lodge Middlesboro

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, an IHG Hotel: Features a full-service spa, a seasonal outdoor pool, and daily. Days Inn by Wyndham Jellico - Tennessee State Line: Features complimentary wireless internet access, a communal pool, and kitchens. Dog-friendly lakefront house with hot tub, central AC, & mountain view: Offers kitchens, a communal pool, and Smart TVs.

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, Bell County Historical Society Museum, and Middlesboro Country Club. 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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