Photo by Alexis Wyrick

Hotels with Pool & Resorts in Middlesboro from NZ$113

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

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Middlesboro Hotels with Pool

Tonight
29 Dec - 30 Dec
Tomorrow
30 Dec - 31 Dec
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Middlesboro hotels with a pool

Property amenity
Holiday Inn Express Middlesboro by IHG

Holiday Inn Express Middlesboro by IHG

Holiday Inn Express Middlesboro by IHG
2.5 star property
Middlesboro
9.6 out of 10, Exceptional, (694)
"Only stayed one night but the hotel was quiet, considering the amount of people that seemed to be there, very clean and the breakfast was great!"
United States
Kevin
The price is NZ$236
includes taxes & fees
11 Jan - 12 Jan 2026
Holiday Inn Express Middlesboro by IHG
Double Room, Smoking
Boone Trail Inn

Boone Trail Inn

Boone Trail Inn
2.0 star property
Middlesboro
7.2 out of 10, Good, (111)
"So the room seemed clean and the owners were vry kind the price was low all in all it was ok for a cheap motel but yall theres roaches i woke up with 1 crawling on the headboard. "
United States
Amy
The price is NZ$143
includes taxes & fees
31 Dec - 1 Jan 2026
Boone Trail Inn
Seasonal outdoor pool
Suburban Studios Middlesboro

Suburban Studios Middlesboro

Suburban Studios Middlesboro
2.0 star property
Middlesboro
8.0 out of 10, Very good, (67)
"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
The price is NZ$147
includes taxes & fees
5 Jan - 6 Jan 2026
Suburban Studios Middlesboro
Seasonal outdoor pool, open 10:00 AM to 10:00 PM, pool loungers
Econo Lodge Middlesboro

Econo Lodge Middlesboro

Econo Lodge Middlesboro
2.0 star property
Middlesboro
7.4 out of 10, Good, (446)
"Clean place with friendly staff. "
United States
James
The price is NZ$169
includes taxes & fees
31 Dec - 1 Jan 2026
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

Pine Mountain State Resort Park
3.0 star property
Pineville
9.0 out of 10, Wonderful, (673)
"Great place to stay!"
United States
William
The price is NZ$242
includes taxes & fees
2 Jan - 3 Jan 2026
Pine Mountain State Resort Park
Front of property
Days Inn by Wyndham Jellico - Tennessee State Line

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, (1002)
"Nice location, nice room, friendly staff and recent remodeling rooms "
United States
Ashley
The price is NZ$145
includes taxes & fees
4 Jan - 5 Jan 2026
Days Inn by Wyndham Jellico - Tennessee State Line
Indoor pool
Holiday Inn Express Williamsburg by IHG

Holiday Inn Express Williamsburg by IHG

Holiday Inn Express Williamsburg by IHG
2.5 star property
Williamsburg
9.0 out of 10, Wonderful, (1004)
"Staff was nice and breakfast was good"
United States
nicole
The price is NZ$223
includes taxes & fees
13 Jan - 14 Jan 2026
Holiday Inn Express Williamsburg by IHG
Business centre
Quality Inn

Quality Inn

Quality Inn
2.5 star property
Barbourville
8.2 out of 10, Very good, (267)
"Room was clean and clerk was nice especially since it was early morning "
United States
Billy
The price is NZ$196
includes taxes & fees
18 Jan - 19 Jan 2026
Quality Inn
Property grounds
Woodlake Lodge Golf and Country Club

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 NZ$250
includes taxes & fees
1 Jan - 2 Jan 2026
Woodlake Lodge Golf and Country Club
BBQ/picnic Area
Super 8 by Wyndham Williamsburg

Super 8 by Wyndham Williamsburg

Super 8 by Wyndham Williamsburg
2.5 star property
Williamsburg
5.8 out of 10, (774)
"Price was right room was clean. Many choices to eat. Staff was pleasant. "
United States
Susan
The price is NZ$113
includes taxes & fees
11 Jan - 12 Jan 2026
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

Econo Lodge Middlesboro

Econo Lodge Middlesboro

10/10 Excellent
"Everything fine "
Daniel 1-night trip
Posted 2 days ago
Econo Lodge Middlesboro

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 daily, a seasonal outdoor pool and free self parking. Super 8 by Wyndham Williamsburg: 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.