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

This weekend
7 Aug - 9 Aug
Next weekend
14 Aug - 16 Aug

Our top choices for Middlesboro hotels with a pool

Outdoor pool, sun loungers

1. Holiday Inn Express Middlesboro by IHG

Holiday Inn Express Middlesboro by IHG
2.5 star property
Middlesboro
9.6 out of 10, Exceptional, (733 reviews)
  • cleanliness
    Splash into mountain adventures with a sun-kissed pool oasis featuring comfy loungers for peak relaxation.
The price is AED 481
AED 530 total
includes taxes & fees
7 Aug - 8 Aug
Holiday Inn Express Middlesboro by IHG
Seasonal outdoor pool, open 10:00 AM to 10:00 PM, sun loungers

2. Econo Lodge Middlesboro

Econo Lodge Middlesboro
2.0 star property
Middlesboro
7.4 out of 10, Good, (495 reviews)
  • cleanliness
    Pristine mountain retreat offers seasonal poolside bliss with lounge chairs for a perfect summer escape in Middlesboro.
The price is AED 327
AED 361 total
includes taxes & fees
18 Aug - 19 Aug
Econo Lodge Middlesboro
Single Room, 1 Queen Bed, Smoking | Bathroom | Free toiletries, towels

3. Boone Trail Inn

Boone Trail Inn
2.0 star property
Middlesboro
7.4 out of 10, Good, (119 reviews)
  • cleanliness
    Dive into summer adventures with a seasonal outdoor pool, perfect for relaxing after a day exploring nearby hiking trails.
The price is AED 289
AED 384 total
includes taxes & fees
8 Aug - 9 Aug
Boone Trail Inn
Seasonal outdoor pool

4. Suburban Studios Middlesboro

Suburban Studios Middlesboro
2.0 star property
Middlesboro
8.2 out of 10, Very Good, (101 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 AED 288
AED 317 total
includes taxes & fees
3 Sep - 4 Sep
Suburban Studios Middlesboro
Aerial view

5. Woodlake Lodge Golf and Country Club

Woodlake Lodge Golf and Country Club
3.0 star property
Tazewell
9.2 out of 10, Wonderful, (153 reviews)
  • cleanliness
    Seasonal lakeside golf retreat with picturesque course, outdoor pool, and tennis courts offering serene relaxation in nature.
The price is AED 606
AED 680 total
includes taxes & fees
6 Aug - 7 Aug
Woodlake Lodge Golf and Country Club
Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers

6. Pine Mountain State Resort Park

Pine Mountain State Resort Park
3.0 star property
Pineville
9.0 out of 10, Wonderful, (745 reviews)
  • cleanliness
    Refreshing mountain escape with a seasonal outdoor pool surrounded by loungers, umbrellas, and panoramic Appalachian views.
The price is AED 562
AED 619 total
includes taxes & fees
7 Aug - 8 Aug
Pine Mountain State Resort Park
Outdoor pool

7. Quality Inn

Quality Inn
2.5 star property
Barbourville
8.2 out of 10, Very Good, (278 reviews)
  • cleanliness
    Outdoor pool beckons with refreshing dips and sun-soaked lounging at this welcoming hotel.
The price is AED 324
AED 367 total
includes taxes & fees
30 Aug - 31 Aug
Quality Inn
Indoor pool

8. Holiday Inn Express Williamsburg by IHG

Holiday Inn Express Williamsburg by IHG
2.5 star property
Williamsburg
9.0 out of 10, Wonderful, (1,005 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 AED 404
AED 450 total
includes taxes & fees
11 Aug - 12 Aug
Holiday Inn Express Williamsburg by IHG
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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Choose what matters most at hotels with a pool in Middlesboro

Breakfast included
Hot tub

Top Middlesboro Hotel Reviews

Quality Inn Harlan

Quality Inn Harlan

10/10 Excellent
"Beds were comfortable. Breakfast was hot. Pool was closed for maintenance"
Whitney 1-night trip
Posted 11 days ago
Quality Inn Harlan

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, an indoor pool, and free self parking. Holiday Inn Express Williamsburg by IHG: Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Days Inn by Wyndham Jellico - Tennessee State Line: Features daily, a seasonal outdoor 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 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.