An aerial view of a town surrounded by mountains, with a mix of residential and commercial buildings, and a highway running through the center.

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

Holiday Inn Express Middlesboro by IHG

Holiday Inn Express Middlesboro by IHG
2.5 star property
Middlesboro
9.6 out of 10, Exceptional, (727 reviews)
  • cleanliness
    Splash into mountain adventures with a sun-kissed pool oasis featuring comfy loungers for peak relaxation.
The price is NT$4,086
NT$4,504 total
includes taxes & fees
Aug 2 - Aug 3
Holiday Inn Express Middlesboro 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, (1,010 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 NT$3,305
NT$3,678 total
includes taxes & fees
Aug 3 - Aug 4
Holiday Inn Express Williamsburg by IHG

Quality Inn

Quality Inn
2.5 star property
Barbourville
8.2 out of 10, Very Good, (276 reviews)
  • cleanliness
    Outdoor pool beckons with refreshing dips and sun-soaked lounging at this welcoming hotel.
The price is NT$2,873
NT$3,258 total
includes taxes & fees
Aug 11 - Aug 12
Quality Inn

Pine Mountain State Resort Park

Pine Mountain State Resort Park
3.0 star property
Pineville
9.0 out of 10, Wonderful, (735 reviews)
  • cleanliness
    Refreshing mountain escape with a seasonal outdoor pool surrounded by loungers, umbrellas, and panoramic Appalachian views.
The price is NT$4,923
NT$5,427 total
includes taxes & fees
Jul 17 - Jul 18
Pine Mountain State Resort Park

Suburban Studios Middlesboro

Suburban Studios Middlesboro
2.0 star property
Middlesboro
8.2 out of 10, Very Good, (96 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 NT$2,521
NT$2,779 total
includes taxes & fees
Aug 5 - Aug 6
Suburban Studios Middlesboro

Boone Trail Inn

Boone Trail Inn
2.0 star property
Middlesboro
7.4 out of 10, Good, (118 reviews)
  • cleanliness
    Dive into summer adventures with a seasonal outdoor pool, perfect for relaxing after a day exploring nearby hiking trails.
The price is NT$2,587
NT$3,420 total
includes taxes & fees
Jul 16 - Jul 17
Boone Trail Inn

Econo Lodge Middlesboro

Econo Lodge Middlesboro
2.0 star property
Middlesboro
7.4 out of 10, Good, (491 reviews)
  • cleanliness
    Pristine mountain retreat offers seasonal poolside bliss with lounge chairs for a perfect summer escape in Middlesboro.
The price is NT$2,752
NT$3,034 total
includes taxes & fees
Aug 11 - Aug 12
Econo Lodge Middlesboro

Woodlake Lodge Golf and Country Club

Woodlake Lodge Golf and Country Club
3.0 star property
Tazewell
9.2 out of 10, Wonderful, (151 reviews)
  • cleanliness
    Seasonal lakeside golf retreat with picturesque course, outdoor pool, and tennis courts offering serene relaxation in nature.
The price is NT$5,311
NT$5,962 total
includes taxes & fees
Jul 13 - Jul 14
Woodlake Lodge Golf and Country Club
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.

Choose what matters most at hotels with a pool in Middlesboro

Top Middlesboro Hotel Reviews

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: Offers daily, an indoor pool, and free self parking. Days Inn by Wyndham Jellico - Tennessee State Line: Provides daily, a seasonal outdoor pool, and free self parking. Holiday Inn Express Williamsburg by IHG: Features free self parking, a seasonal outdoor pool, and complimentary wireless internet access.
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 Cumberland Gap National Historical Park, Middlesboro Country Club, and Middlesboro Mall. 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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