Photo by Alexis Wyrick

Find Hotels with a Pool in Middlesboro, KY

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Middlesboro Hotels with a Pool

Our top choices for Middlesboro hotels with a pool

Property amenity
Holiday Inn Express Middlesboro by IHG

Holiday Inn Express Middlesboro by IHG

Holiday Inn Express Middlesboro by IHG
2.5 star property
Middlesboro
9.6 out of 10, Exceptional, (692)
"Clean hotel, good breakfast options."
United States
Harold
The price is ₩174,370
₩192,221 total
includes taxes & fees
Dec 21 - Dec 22
Holiday Inn Express Middlesboro by IHG
Double Room, Smoking | Desk, blackout drapes, free WiFi, bed sheets
Boone Trail Inn

Boone Trail Inn

Boone Trail Inn
2.0 star property
Middlesboro
7.2 out of 10, Good, (110)
"Place was clean. AC worked good. "
United States
David
The price is ₩99,127
₩133,563 total
includes taxes & fees
Dec 19 - Dec 20
Boone Trail Inn
Seasonal outdoor pool
Suburban Studios Middlesboro

Suburban Studios Middlesboro

Suburban Studios Middlesboro
2.0 star property
Middlesboro
8.0 out of 10, Very Good, (67)
"The newly renovated very clean room was comfortable and clean. All staff were very friendly and we had no issues with our stay. Would stay again when in this area! "
United States
Becky
The price is ₩116,647
₩128,593 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Suburban Studios Middlesboro
Seasonal outdoor pool, open 10:00 AM to 10:00 PM, sun loungers
Econo Lodge Middlesboro

Econo Lodge Middlesboro

Econo Lodge Middlesboro
2.0 star property
Middlesboro
7.4 out of 10, Good, (445)
"Clean place with friendly staff. "
United States
James
The price is ₩117,921
₩129,997 total
includes taxes & fees
Dec 21 - Dec 22
Econo Lodge Middlesboro
Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers
Pine Mountain State Resort Park

Pine Mountain State Resort Park

Pine Mountain State Resort Park
3.0 star property
Pineville
9.0 out of 10, Wonderful, (669)
"The check in and out was very easy. Staff was pleasant and helpful. The cottage was very clean and well kept. The outside lighting could have been better as we arrived in the dark and it was hard to see. Overall great stay. "
United States
DeAnna
The price is ₩164,419
₩181,263 total
includes taxes & fees
Dec 26 - Dec 27
Pine Mountain State Resort Park
Front of property
Days Inn by Wyndham Jellico - Tennessee State Line

Days Inn by Wyndham Jellico - Tennessee State Line

Days Inn by Wyndham Jellico - Tennessee State Line
2.0 star property
Jellico
7.2 out of 10, Good, (1002)
"Very clean and quiet I loved and enjoyed my 3 nights and 4 day stay!!! "
United States
Antoninette
The price is ₩108,673
₩124,159 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Days Inn by Wyndham Jellico - Tennessee State Line
Indoor pool
Holiday Inn Express Williamsburg by IHG

Holiday Inn Express Williamsburg by IHG

Holiday Inn Express Williamsburg by IHG
2.5 star property
Williamsburg
9.0 out of 10, Wonderful, (1001)
"Staff and room were great. We did not stay for breakfast because we wanted to get on the road home ASAP. "
United States
ROBERT
The price is ₩169,937
₩192,176 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Holiday Inn Express Williamsburg by IHG
Business center
Quality Inn

Quality Inn

Quality Inn
2.5 star property
Barbourville
8.2 out of 10, Very Good, (267)
"Room was clean and clerk was nice especially since it was early morning "
United States
Billy
The price is ₩152,289
₩172,727 total
includes taxes & fees
Jan 15 - Jan 16, 2026
Quality Inn
Property grounds
Woodlake Lodge Golf and Country Club

Woodlake Lodge Golf and Country Club

Woodlake Lodge Golf and Country Club
3.0 star property
Tazewell
9.4 out of 10, Exceptional, (142)
"Gym was closed, restaurant was closed... pool was nice. Course is beautiful."
United States
Daniel
The price is ₩190,912
₩214,306 total
includes taxes & fees
Jan 15 - Jan 16, 2026
Woodlake Lodge Golf and Country Club
BBQ/picnic area
Super 8 by Wyndham Williamsburg

Super 8 by Wyndham Williamsburg

Super 8 by Wyndham Williamsburg
2.5 star property
Williamsburg
5.8 out of 10, (772)
"Price was right room was clean. Many choices to eat. Staff was pleasant. "
United States
Susan
The price is ₩85,412
₩95,063 total
includes taxes & fees
Dec 18 - Dec 19
Super 8 by Wyndham Williamsburg
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Top Middlesboro Hotel Reviews

Pine Mountain State Resort Park

Pine Mountain State Resort Park

10/10 Excellent
"The check in and out was very easy. Staff was pleasant and helpful. The cottage was very clean and well kept. The outside lighting could have been better as we arrived in the dark and it was hard to see. Overall great stay. "
DeAnna 1-night trip
Posted 8 days ago
Pine Mountain State Resort Park

Frequently asked questions

What are some accommodations with pools in Middlesboro?
Sleep Inn & Suites Middlesboro: Offers buffet, an outdoor pool, and free self parking. Holiday Inn Express Middlesboro by IHG: Provides continental, a seasonal outdoor pool, and free self parking. Econo Lodge Middlesboro: Features free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Boone Trail Inn: Offers 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.
What is there to see and do in Middlesboro?
Spend some time experiencing the great outdoors at Kentucky Ridge State Forest. During your stay, check out sights such as Middlesboro Mall, Cumberland Gap National Historical Park, 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.