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Find Hotels with a Pool in Middlesboro, KY

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Check availability on Middlesboro Hotels with a Pool

Top Middlesboro Hotels with a Pool

Double Room, Smoking | Desk, blackout drapes, free WiFi, bed sheets
Boone Trail Inn

Boone Trail Inn

2.0 star property
Middlesboro
  • Pool
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Housekeeping
7.2 out of 10, Good, (108)
Seasonal swimming awaits at this renovated motel, offering a refreshing pool experience from May to September. Friendly staff ensure comfort while nature enthusiasts appreciate proximity to hiking trails, creating an ideal summer escape.
$77 nightly
The price is $85
Dec 12 - Dec 13
Total with taxes and fees
Boone Trail Inn
Property amenity
Holiday Inn Express Middlesboro by IHG

Holiday Inn Express Middlesboro by IHG

2.5 star property
Middlesboro
  • Outdoor pool
  • Pool loungers
9.6 out of 10, Exceptional, (690)
Sparkling blue waters invite guests to plunge into the outdoor pool after hiking nearby mountain trails. This recently renovated hotel offers pristine rooms with plush bedding and a complimentary breakfast buffet to fuel outdoor adventures.
$118 nightly
The price is $130
Nov 23 - Nov 24
Total with taxes and fees
Holiday Inn Express Middlesboro by IHG
Seasonal outdoor pool
Suburban Studios Middlesboro

Suburban Studios Middlesboro

2.0 star property
Middlesboro
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Restaurant
8.0 out of 10, Very Good, (64)
Dive into summer fun at the seasonal outdoor pool, where sunshine and relaxation await after exploring Middlesboro. This recently remodeled hotel offers clean, sparkling rooms with kitchenettes and rainfall showers for complete comfort.
$76 nightly
The price is $83
Nov 18 - Nov 19
Total with taxes and fees
Suburban Studios Middlesboro
Seasonal outdoor pool, open 10:00 AM to 10:00 PM, sun loungers
Econo Lodge Middlesboro

Econo Lodge Middlesboro

2.0 star property
Middlesboro
  • Pool loungers
7.2 out of 10, Good, (441)
Splash into summer at this mountain getaway's seasonal outdoor pool, complete with comfortable loungers for ultimate relaxation. Freshly renovated rooms, friendly staff, and complimentary continental breakfast create a rejuvenating experience.
$75 nightly
The price is $83
Nov 16 - Nov 17
Total with taxes and fees
Econo Lodge Middlesboro
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
  • Outdoor pool
  • Pool loungers
9.0 out of 10, Wonderful, (655)
Sparkling waters await at this seasonal mountain pool, where guests soak up stunning Appalachian vistas from comfortable loungers. Beyond swimming, the hotel offers an 18-hole golf course, hiking trails, and flavorful American cuisine at Mountain View restaurant.
$84 nightly
The price is $93
Nov 12 - Nov 13
Total with taxes and fees
Pine Mountain State Resort Park
Front of property
Days Inn by Wyndham Jellico - Tennessee State Line

Days Inn by Wyndham Jellico - Tennessee State Line

2.0 star property
Jellico
  • Outdoor pool
  • Pool loungers
  • Hot tub
7.2 out of 10, Good, (1007)
Surrounded by mountain scenery, this hotel's refreshing outdoor pool area beckons with comfortable sun loungers and umbrellas. After exploring nearby hiking trails, guests can soak tired muscles in the relaxing hot tub before retreating to clean, comfortable rooms.
$63 nightly
The price is $72
Nov 23 - Nov 24
Total with taxes and fees
Days Inn by Wyndham Jellico - Tennessee State Line
Indoor pool
Quality Inn

Quality Inn

2.5 star property
Harlan
  • Indoor pool
8.6 out of 10, Excellent, (330)
Swimming sessions await at the pristine indoor pool, accessible from 9:00 AM to 9:00 PM daily. Beyond aquatic pleasures, guests appreciate the extremely comfortable beds, friendly staff, and complimentary continental breakfast served in an impeccably clean dining area.
$90 nightly
The price is $102
Dec 7 - Dec 8
Total with taxes and fees
Quality Inn
Business center
Quality Inn

Quality Inn

2.5 star property
Barbourville
  • Outdoor pool
8.2 out of 10, Very Good, (264)
Mountain escape awaits with a pristine outdoor pool where guests can unwind after exploring Dr. Thomas Walker State Historic Site. Friendly staff ensures comfort while free continental breakfast fuels adventurous days in scenic Kentucky.
$102 nightly
The price is $115
Nov 23 - Nov 24
Total with taxes and fees
Quality Inn
Indoor pool
Holiday Inn Express Williamsburg by IHG

Holiday Inn Express Williamsburg by IHG

2.5 star property
Williamsburg
  • Indoor pool
9.0 out of 10, Wonderful, (1001)
Swimming enthusiasts relish the pristine indoor pool that complements this hotel's spotlessly maintained accommodations. Premium bedding with pillowtop mattresses awaits after invigorating laps, while the consistently excellent breakfast earns rave reviews from satisfied guests.
$118 nightly
The price is $131
Dec 10 - Dec 11
Total with taxes and fees
Holiday Inn Express Williamsburg by IHG
Property grounds
Woodlake Lodge Golf and Country Club

Woodlake Lodge Golf and Country Club

3.0 star property
Tazewell
  • Outdoor pool
9.4 out of 10, Exceptional, (141)
Splash into summer at the seasonal outdoor pool, surrounded by pristine golf greens and tennis courts. Friendly staff ensure exceptional service while the peaceful lakeside setting, complete with on-site restaurants and bar, creates a rejuvenating escape.
$145 nightly
The price is $163
Nov 12 - Nov 13
Total with taxes and fees
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.
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Top Middlesboro Hotel Reviews

Pine Mountain State Resort Park

Pine Mountain State Resort Park

10/10 Excellent
"Staff were amazing! Very unique experience in the cottage and the fireplace was really special highly recommended!"
Andrew 1-night trip
Posted 3 days ago
Pine Mountain State Resort Park

Frequently asked questions

What are some accommodations with pools in Middlesboro?
Holiday Inn Express Middlesboro by IHG: Features buffet, an outdoor pool, and free self parking. Sleep Inn & Suites Middlesboro: Provides continental, a seasonal outdoor pool, and free self parking. Econo Lodge Middlesboro: Features free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Boone Trail Inn: Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Pine Mountain State Resort Park: Features 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 Country Club, Middlesboro Mall, and Cumberland Gap National Historical Park. 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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