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Find Hotels with a Pool in Middlesboro, KY

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Check availability on Middlesboro Hotels with a Pool

Our top choices for Middlesboro hotels with a pool

Outdoor pool, sun loungers
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, (691)
"Clean hotel, good breakfast options."
United States
Harold
The price is AED 433
AED 478 total
includes taxes & fees
21 Dec - 22 Dec
Holiday Inn Express Middlesboro by IHG
Single Room, 1 Queen Bed, Smoking | Air conditioning
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 AED 243
AED 329 total
includes taxes & fees
13 Dec - 14 Dec
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, (66)
"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 AED 292
AED 321 total
includes taxes & fees
29 Dec - 30 Dec
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 AED 293
AED 323 total
includes taxes & fees
21 Dec - 22 Dec
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 AED 411
AED 453 total
includes taxes & fees
13 Dec - 14 Dec
Pine Mountain State Resort Park
Outdoor pool, open 9 AM to 10 PM, pool umbrellas, sun loungers
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, (1001)
"Very clean and quiet I loved and enjoyed my 3 nights and 4 day stay!!! "
United States
Antoninette
The price is AED 275
AED 315 total
includes taxes & fees
1 Jan - 2 January 2026
Days Inn by Wyndham Jellico - Tennessee State Line
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 AED 365
AED 414 total
includes taxes & fees
11 Jan - 12 January 2026
Quality Inn
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, (1000)
"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 AED 342
AED 386 total
includes taxes & fees
23 Dec - 24 Dec
Holiday Inn Express Williamsburg by IHG
Aerial view
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 AED 477
AED 536 total
includes taxes & fees
4 Jan - 5 January 2026
Woodlake Lodge Golf and Country Club
Seasonal outdoor pool, sun loungers
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, (771)
"Price was right room was clean. Many choices to eat. Staff was pleasant. "
United States
Susan
The price is AED 212
AED 236 total
includes taxes & fees
14 Dec - 15 Dec
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.
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Top Middlesboro Hotel Reviews

Quality Inn

Quality Inn

10/10 Excellent
"The room was very clean, staff was extremely friendly, polite, and helpful."
Katrina 2-night trip
Posted 3 days ago
Quality Inn

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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 free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Pine Mountain State Resort Park: Features daily, an indoor pool, and free self parking.
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.