Photo by Alexis Wyrick

Hotels with Pool & Resorts in Middlesboro from NZ$127

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

Best Middlesboro Hotels with Pool

Double Room, Smoking
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.
The price is NZ$151
includes taxes & fees
11 Dec - 12 Dec
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.
The price is NZ$231
includes taxes & fees
23 Nov - 24 Nov
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.
The price is NZ$148
includes taxes & fees
7 Dec - 8 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
  • 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.
The price is NZ$147
includes taxes & fees
16 Nov - 17 Nov
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
  • 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 flavourful American cuisine at Mountain View restaurant.
The price is NZ$214
includes taxes & fees
25 Nov - 26 Nov
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 spa pool before retreating to clean, comfortable rooms.
The price is NZ$127
includes taxes & fees
8 Dec - 9 Dec
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.
The price is NZ$182
includes taxes & fees
7 Dec - 8 Dec
Quality Inn
Business centre
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.
The price is NZ$203
includes taxes & fees
16 Nov - 17 Nov
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 accommodation. Premium bedding with pillowtop mattresses awaits after invigorating laps, while the consistently excellent breakfast earns rave reviews from satisfied guests.
The price is NZ$232
includes taxes & fees
10 Dec - 11 Dec
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.
The price is NZ$289
includes taxes & fees
12 Nov - 13 Nov
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.
View all properties

Top Middlesboro Hotel Reviews

Quality Inn

Quality Inn

10/10 Excellent
"The staff was really friendly and the beds were very comfortable. "
Marla 2-night trip
Posted 2 days ago
Quality Inn

Explore a world of travel with Expedia

Frequently asked questions

What are some accommodation options 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, visit 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 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.