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Middlesboro Hotels with Swimming Pool

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Check availability on Middlesboro Hotels with Swimming Pools

Tonight
30 Nov - 1 Dec
Tomorrow
1 Dec - 2 Dec
Next weekend
5 Dec - 7 Dec
In two weeks
12 Dec - 14 Dec

Top Middlesboro Hotels with Swimming Pools

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, (690)
"Clean hotel, good breakfast options."
United States
Harold
The price is RM475
RM524 total
includes taxes & fees
21 Dec - 22 Dec
Holiday Inn Express Middlesboro by IHG
Desk, blackout curtains, free WiFi, bed sheets
Boone Trail Inn

Boone Trail Inn

2.0 star property
Middlesboro
7.2 out of 10, Good, (109)
"Place was clean. AC worked good. "
United States
David
The price is RM279
RM376 total
includes taxes & fees
1 Dec - 2 Dec
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)
"Didn't stay as we found a better location in Cumberland Gap. "
United States
Alan
The price is RM312
RM344 total
includes taxes & fees
6 Dec - 7 Dec
Suburban Studios Middlesboro
Seasonal outdoor pool, open 10:00 AM to 10:00 PM, pool loungers
Econo Lodge Middlesboro

Econo Lodge Middlesboro

2.0 star property
Middlesboro
7.4 out of 10, Good, (443)
"Clean place with friendly staff. "
United States
James
The price is RM330
RM364 total
includes taxes & fees
1 Dec - 2 Dec
Econo Lodge Middlesboro
Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, pool loungers
Pine Mountain State Resort Park

Pine Mountain State Resort Park

3.0 star property
Pineville
9.0 out of 10, Wonderful, (662)
"Staff were amazing! Very unique experience in the cottage and the fireplace was really special highly recommended!"
United States
Andrew
The price is RM451
RM497 total
includes taxes & fees
9 Dec - 10 Dec
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, (1003)
"We really enjoyed our stay! "
United States
Andrea Strode
The price is RM410
RM464 total
includes taxes & fees
2 Dec - 3 Dec
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, (1007)
"Very clean and quiet I loved and enjoyed my 3 nights and 4 day stay!!! "
United States
Antoninette
The price is RM306
RM349 total
includes taxes & fees
1 Dec - 2 Dec
Days Inn by Wyndham Jellico - Tennessee State Line
Business centre
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
The price is RM428
RM485 total
includes taxes & fees
7 Dec - 8 Dec
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
The price is RM579
RM649 total
includes taxes & fees
31 Dec - 1 Jan 2026
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, (764)
"Love the Mint.."
United States
Tracy
The price is RM246
RM274 total
includes taxes & fees
1 Dec - 2 Dec
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.
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Top Middlesboro Hotel Reviews

Days Inn by Wyndham Jellico - Tennessee State Line

Days Inn by Wyndham Jellico - Tennessee State Line

10/10 Excellent
"We did not visit the pool,but it looked nice. Staff was very friendly and helpful. Especially the front desk people. Our housekeeper was very helpful. Also,very convenient to the highway."
Mindell 1-night trip
Posted 13 days ago
Days Inn by Wyndham Jellico - Tennessee State Line
Quality Inn

Quality Inn

10/10 Excellent
"I recently stayed 2 nights here. My stay was wonderful. Everything was clean and fresh. I actually felt at home here. Great job!!!"
Tonya 1-night trip
Posted 3 months ago
Quality Inn

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 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, visit 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 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.