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

Tonight
Aug 30 - Aug 31
Tomorrow
Aug 31 - Sep 1
Next weekend
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13

Our top choices for Middlesboro hotels with a pool

A modern bathroom with a glass-enclosed shower, two sinks, and a large mirror.
A swimming pool with lounge chairs and a building in the background.
A two-story hotel with a covered entrance and a parking lot in front.
A hotel reception desk with a digital kiosk, a computer, and a sign for Holiday Inn Express.

1. Holiday Inn Express Middlesboro by IHG

Holiday Inn Express Middlesboro by IHG
Middlesboro
  • Splash into mountain adventures with a sun-kissed pool oasis featuring comfy loungers for peak relaxation.
₩191,311
₩210,896 total
includes taxes & fees
Sep 6 - Sep 7
Holiday Inn Express Middlesboro by IHG
A swimming pool with a metal fence, surrounded by white lounge chairs and a building with a blue roof and red and white decorations.
A reception area with a striped armchair, a counter, and a view of the parking lot through glass doors.
A modern bathroom with a large mirror, a sink, and a shower area.
A dining area with a buffet, chairs, a table, a chandelier, and a view through the window.

2. Econo Lodge Middlesboro

Econo Lodge Middlesboro
Middlesboro
  • Pristine mountain retreat offers seasonal poolside bliss with lounge chairs for a perfect summer escape in Middlesboro.
₩110,245
₩121,535 total
includes taxes & fees
Sep 6 - Sep 7
Econo Lodge Middlesboro
A swimming pool with lounge chairs and a building in the background.
A bathroom with a bathtub, a toilet, and a towel rack with towels.
A modern kitchen with wooden cabinets, a white countertop, a built-in microwave, and a refrigerator.
A restaurant with striped chairs, a wooden counter, and a chandelier.

3. Suburban Studios Middlesboro

Suburban Studios Middlesboro
Middlesboro
  • Escape the ordinary at this freshly remodeled hotel with a sparkling seasonal pool and newly updated rooms for summer relaxation.
₩107,795
₩118,834 total
includes taxes & fees
Sep 20 - Sep 21
Suburban Studios Middlesboro
A bathroom with a bathtub, toilet, and sink.
A white portable air conditioner mounted on a wall with a control panel, a power outlet, and a plastic bag hanging from the bottom.
A motel with a two-story structure, a parking lot, and a stone wall.
A hotel room with a large bed, two bedside lamps, a nightstand, a chair, and a painting on the wall.

4. Boone Trail Inn

Boone Trail Inn
Middlesboro
  • Dive into summer adventures with a seasonal outdoor pool, perfect for relaxing after a day exploring nearby hiking trails.
₩111,794
₩147,517 total
includes taxes & fees
Aug 31 - Sep 1
Boone Trail Inn
A swimming pool area with lounge chairs and umbrellas.
A rustic interior with wooden beams, a fireplace, and a bar area.
A natural setting with a clear pond surrounded by rocks and trees, and rows of blue chairs arranged for an event.
A picnic table and stone wall in a forested area with a view of distant mountains.

5. Pine Mountain State Resort Park

Pine Mountain State Resort Park
Pineville
  • Refreshing mountain escape with a seasonal outdoor pool surrounded by loungers, umbrellas, and panoramic Appalachian views.
₩198,124
₩218,411 total
includes taxes & fees
Sep 4 - Sep 5
Pine Mountain State Resort Park
A hotel room with a coffee machine, a bed, and a window with a view.
An indoor swimming pool with clear pool rules and no diving allowed signs.
A Holiday Inn Express hotel with a parking lot and multiple vehicles.
A hotel lobby with seating areas, a reception desk, and a large window.

6. Holiday Inn Express Williamsburg by IHG

Holiday Inn Express Williamsburg by IHG
Williamsburg
  • Dive into poolside relaxation at this clean, comfortable hotel with an indoor oasis just steps from Kentucky Splash Water Park.
₩151,397
₩168,505 total
includes taxes & fees
Sep 7 - Sep 8
Holiday Inn Express Williamsburg by IHG

7. Quality Inn

Quality Inn
Barbourville
  • Outdoor pool beckons with refreshing dips and sun-soaked lounging at this welcoming hotel.
₩140,387
₩159,225 total
includes taxes & fees
Sep 28 - Sep 29
Quality Inn
An aerial view of a golf course with multiple ponds, a clubhouse, and surrounding wooded areas.
A bar area with wooden chairs and a bar counter. There are framed pictures on the wall and a television above the bar.
A hotel room with a large bed, two bedside tables with lamps, a small desk, and a red armchair.
A golf course with a clubhouse, a flag, and a parking area with cars.

8. Woodlake Lodge Golf and Country Club

Woodlake Lodge Golf and Country Club
Tazewell
  • Seasonal lakeside golf retreat with picturesque course, outdoor pool, and tennis courts offering serene relaxation in nature.
₩227,096
₩254,912 total
includes taxes & fees
Aug 31 - Sep 1
Woodlake Lodge Golf and Country Club
View all properties

Choose what matters most at hotels with a pool in Middlesboro

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Middlesboro Hotel Reviews

Pine Mountain State Resort Park

Pine Mountain State Resort Park

10/10 Excellent
"We enjoyed our stay in a clean and comfortable cabin. The park is beautiful."
David 2-night trip
Posted 1 day ago
Pine Mountain State Resort Park
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 1 month ago
Quality Inn Harlan

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 daily, a seasonal outdoor pool, and free self parking. Suburban Studios Middlesboro: Offers 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.
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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