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

Middlesboro Hotel Guide - Hotels with Pool in Middlesboro, Kentucky

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Check availability on Middlesboro Hotels with Pool

Tonight
22 Aug - 23 Aug
Tomorrow
23 Aug - 24 Aug
Next weekend
28 Aug - 30 Aug
In two weeks
4 Sept - 6 Sept

Our top choices for Middlesboro hotels with a pool

A swimming pool with lounge chairs and a covered area, surrounded by trees.
A modern office space with two desks, computers, and a large window.
A modern bathroom with a glass-enclosed shower, two sinks, and a large mirror.
A modern building entrance with a covered walkway, large windows, and potted plants.

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.
€128
includes taxes & fees
23 Aug - 24 Aug
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 modern bathroom with a large mirror, a sink, and a shower area.
A hotel room with two beds, a sofa, a nightstand with a lamp, and a framed picture on the wall.
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.
€84
includes taxes & fees
30 Aug - 31 Aug
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 restaurant with striped chairs, a wooden counter, and a chandelier.
A modern kitchen with wooden cabinets, a white countertop, a built-in microwave, and a refrigerator.

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.
€74
includes taxes & fees
14 Sept - 15 Sept
Suburban Studios Middlesboro
A bathroom with a bathtub, toilet, and sink.
A small room with a wooden desk, two chairs, a cabinet, and a patterned floor.
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 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.
€92
includes taxes & fees
25 Aug - 26 Aug
Boone Trail Inn
A swimming pool area with lounge chairs and umbrellas.
A picnic table and stone wall in a forested area with a view of distant mountains.
A rustic interior with wooden beams, a fireplace, and a bar area.
A rustic interior with wooden beams, leather sofas, rocking chairs, and a bar area.

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.
€144
includes taxes & fees
28 Aug - 29 Aug
Pine Mountain State Resort Park
An indoor swimming pool with clear pool rules, a lifeguard on duty sign, and a no diving allowed sign.
A Holiday Inn Express building with a parking lot and a covered entrance.
A hotel room with a coffee machine, a bed, and a window with a view.
A buffet with labeled food sections including omelets and cheese.

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.
€105
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn Express Williamsburg by IHG
A large, single-story building with a blue roof and white columns, featuring multiple balconies and a covered walkway.

7. Quality Inn

Quality Inn
Barbourville
  • Outdoor pool beckons with refreshing dips and sun-soaked lounging at this welcoming hotel.
€94
includes taxes & fees
20 Sept - 21 Sept
Quality Inn
An aerial view of a golf course with multiple ponds, a clubhouse, and surrounding wooded areas.
A hotel room with a large bed, two bedside tables with lamps, a small desk, and a red armchair.
A bar area with wooden chairs and a bar counter. There are framed pictures on the wall and a television above the bar.
A building with a covered entrance, stone pillars, and a clear sky.

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.
€159
includes taxes & fees
23 Aug - 24 Aug
Woodlake Lodge Golf and Country Club
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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 had a great one night stay after visiting Cumberland Gap National historic area. Our family of 6 stayed in one of the cottages. Cottage was was very clean and updated but did smell a little musty. We had dinner at the lodge while enjoying the view and swam in the pool. We brought our own food for breakfast which we were able to cook in the cottage. Then we checked out and drove up to the top of the mountain amd hiked to chained rock. Its all downhill on the way there but not too far (half of a mile). Overall it was a great stop on our Kentucky vacation."
Heather 1-night trip
Posted 5 days 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 accommodation options 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, visit sights such as Cumberland Gap National Historical Park, Middlesboro Mall 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 has an outdoor pool if you plan to visit Middlesboro in the warmest months of July, August or June, when the average temp is 22°C. Accommodation with an indoor pool may be the way to go if you come to town during the coldest months of January, February or December, when the average temperature is 5°C.