Photo by Alexis Wyrick

Find Hotels with a Pool in Middlesboro, KY

Start date: Check-in selected.
To Date
End date: Check-out

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Middlesboro Hotels with a Pool

Tonight
Dec 5 - Dec 6
Tomorrow
Dec 6 - Dec 7
This weekend
Dec 5 - Dec 7
Next weekend
Dec 12 - Dec 14

Top Middlesboro Hotels with a Pool

Property amenity
Holiday Inn Express Middlesboro by IHG

Holiday Inn Express Middlesboro by IHG

2.5 star property
Middlesboro
9.6 out of 10, Exceptional, (691)
"Clean hotel, good breakfast options."
United States
Harold
$115 nightly
The price is $127
Dec 21 - Dec 22
Total with taxes and fees
Holiday Inn Express Middlesboro by IHG
Double Room, Smoking | Desk, blackout drapes, free WiFi, bed sheets
Boone Trail Inn

Boone Trail Inn

2.0 star property
Middlesboro
7.2 out of 10, Good, (110)
"Place was clean. AC worked good. "
United States
David
$79 nightly
The price is $88
Dec 6 - Dec 7
Total with taxes and fees
Boone Trail Inn
Seasonal outdoor pool
Suburban Studios Middlesboro

Suburban Studios Middlesboro

2.0 star property
Middlesboro
8.0 out of 10, Very Good, (66)
"The newly renovated very clean room was comfortable and clean. All staff were very friendly and we had no issues with our stay. Would stay again when in this area! "
United States
Becky
$75 nightly
The price is $83
Dec 11 - Dec 12
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
7.4 out of 10, Good, (445)
"Clean place with friendly staff. "
United States
James
$80 nightly
The price is $88
Dec 7 - Dec 8
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
9.0 out of 10, Wonderful, (668)
"Staff were amazing! Very unique experience in the cottage and the fireplace was really special highly recommended!"
United States
Andrew
$98 nightly
The price is $108
Dec 10 - Dec 11
Total with taxes and fees
Pine Mountain State Resort Park
Indoor pool
Holiday Inn Express Williamsburg by IHG

Holiday Inn Express Williamsburg by IHG

2.5 star property
Williamsburg
9.0 out of 10, Wonderful, (1001)
"We really enjoyed our stay! "
United States
Andrea Strode
$117 nightly
The price is $130
Dec 22 - Dec 23
Total with taxes and fees
Holiday Inn Express Williamsburg by IHG
Front of property
Days Inn by Wyndham Jellico - Tennessee State Line

Days Inn by Wyndham Jellico - Tennessee State Line

2.0 star property
Jellico
7.2 out of 10, Good, (1000)
"Very clean and quiet I loved and enjoyed my 3 nights and 4 day stay!!! "
United States
Antoninette
$69 nightly
The price is $79
Dec 7 - Dec 8
Total with taxes and fees
Days Inn by Wyndham Jellico - Tennessee State Line
Business center
Quality Inn

Quality Inn

2.5 star property
Barbourville
8.2 out of 10, Very Good, (266)
"Room was clean and clerk was nice especially since it was early morning "
United States
Billy
$103 nightly
The price is $117
Jan 4 - Jan 5, 2026
Total with taxes and fees
Quality Inn
Property grounds
Woodlake Lodge Golf and Country Club

Woodlake Lodge Golf and Country Club

3.0 star property
Tazewell
9.4 out of 10, Exceptional, (142)
"Gym was closed, restaurant was closed... pool was nice. Course is beautiful."
United States
Daniel
$130 nightly
The price is $146
Jan 1 - Jan 2, 2026
Total with taxes and fees
Woodlake Lodge Golf and Country Club
BBQ/picnic area
Super 8 by Wyndham Williamsburg

Super 8 by Wyndham Williamsburg

2.5 star property
Williamsburg
5.8 out of 10, (766)
"Price was right room was clean. Many choices to eat. Staff was pleasant. "
United States
Susan
$58 nightly
The price is $64
Dec 8 - Dec 9
Total with taxes and fees
Super 8 by Wyndham Williamsburg
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.
View all properties

Top Middlesboro Hotel Reviews

Quality Inn

Quality Inn

10/10 Excellent
"It was short stay met our needs "
Karen 1-night trip
Posted 3 days ago
Quality Inn

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 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 Mall, Cumberland Gap National Historical Park, 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 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.

Explore a world of travel with Expedia