Find Hotels with a Pool in Middlesboro, KY

  • 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

Next weekend
Jun 5 - Jun 7
In two weeks
Jun 12 - Jun 14

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
2.5 star property
Middlesboro
9.6 out of 10, Exceptional, (722 reviews)
  • cleanliness
    Splash into mountain adventures with a sun-kissed pool oasis featuring comfy loungers for peak relaxation.
The price is ₩216,644
₩238,835 total
includes taxes & fees
Jun 4 - Jun 5
Holiday Inn Express Middlesboro by IHG
Seasonal outdoor pool, open 10:00 AM to 10:00 PM, sun loungers

Econo Lodge Middlesboro

Econo Lodge Middlesboro
2.0 star property
Middlesboro
7.4 out of 10, Good, (472 reviews)
  • cleanliness
    Pristine mountain retreat offers seasonal poolside bliss with lounge chairs for a perfect summer escape in Middlesboro.
The price is ₩133,898
₩147,609 total
includes taxes & fees
May 31 - Jun 1
Econo Lodge Middlesboro
Seasonal outdoor pool

Suburban Studios Middlesboro

Suburban Studios Middlesboro
2.0 star property
Middlesboro
8.2 out of 10, Very Good, (88 reviews)
  • cleanliness
    Escape the ordinary at this freshly remodeled hotel with a sparkling seasonal pool and newly updated rooms for summer relaxation.
The price is ₩131,069
₩144,490 total
includes taxes & fees
Jun 21 - Jun 22
Suburban Studios Middlesboro
Single Room, 1 Queen Bed, Smoking | Bathroom | Free toiletries, towels

Boone Trail Inn

Boone Trail Inn
2.0 star property
Middlesboro
7.2 out of 10, Good, (113 reviews)
  • cleanliness
    Dive into summer adventures with a seasonal outdoor pool, perfect for relaxing after a day exploring nearby hiking trails.
The price is ₩104,842
₩140,133 total
includes taxes & fees
Jun 5 - Jun 6
Boone Trail Inn
Indoor pool

Holiday Inn Express Williamsburg by IHG

Holiday Inn Express Williamsburg by IHG
2.5 star property
Williamsburg
9.0 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Dive into poolside relaxation at this clean, comfortable hotel with an indoor oasis just steps from Kentucky Splash Water Park.
The price is ₩197,086
₩219,357 total
includes taxes & fees
Jun 8 - Jun 9
Holiday Inn Express Williamsburg by IHG
Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers

Pine Mountain State Resort Park

Pine Mountain State Resort Park
3.0 star property
Pineville
9.0 out of 10, Wonderful, (725 reviews)
  • cleanliness
    Refreshing mountain escape with a seasonal outdoor pool surrounded by loungers, umbrellas, and panoramic Appalachian views.
The price is ₩218,976
₩241,408 total
includes taxes & fees
Jun 1 - Jun 2
Pine Mountain State Resort Park
Aerial view

Woodlake Lodge Golf and Country Club

Woodlake Lodge Golf and Country Club
3.0 star property
Tazewell
9.4 out of 10, Exceptional, (149 reviews)
  • cleanliness
    Seasonal lakeside golf retreat with picturesque course, outdoor pool, and tennis courts offering serene relaxation in nature.
The price is ₩246,424
₩276,607 total
includes taxes & fees
Jun 10 - Jun 11
Woodlake Lodge Golf and Country Club
Business center

Quality Inn

Quality Inn
2.5 star property
Barbourville
8.2 out of 10, Very Good, (274 reviews)
  • cleanliness
    Outdoor pool beckons with refreshing dips and sun-soaked lounging at this welcoming hotel.
The price is ₩164,363
₩186,421 total
includes taxes & fees
Jun 7 - Jun 8
Quality Inn
Seasonal outdoor pool, sun loungers

Super 8 by Wyndham Williamsburg

Super 8 by Wyndham Williamsburg
2.5 star property
Williamsburg
5.6 out of 10, (831 reviews)
  • cleanliness
    Seasonal pool with sun loungers offers relaxation amid amenities and mini golf at quiet hotel.
The price is ₩115,107
₩128,114 total
includes taxes & fees
Jun 16 - Jun 17
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

Choose what matters most at hotels with a pool in Middlesboro

Breakfast included
Hot tub

Top Middlesboro Hotel Reviews

Days Inn by Wyndham Jellico - Tennessee State Line

Days Inn by Wyndham Jellico - Tennessee State Line

6/10 Okay
"Expedia was asking me to review and said that guest rave about the pool. The pool was bright green. Informed upon check in that it isn’t in use. It was supposed to be filled in. Breakfast was offered in the morning, but there was really nothing offered. The beds were nice. Everything else was mediocre. You get what you pay for. :)"
Debra 1-night trip
Posted 17 hours ago
Days Inn by Wyndham Jellico - Tennessee State Line

Frequently asked questions

What are some accommodations with pools in Middlesboro?
Sleep Inn & Suites Middlesboro: Offers continental, a seasonal outdoor pool, and free self parking. Econo Lodge Middlesboro: Provides buffet, an outdoor pool, and free self parking. Holiday Inn Express Middlesboro by IHG: Features daily, a seasonal outdoor pool, and free self parking. Suburban Studios Middlesboro: Features daily, a seasonal outdoor pool, and free self parking. Days Inn by Wyndham Jellico - Tennessee State Line: Offers 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.