Title: Book the Best Hotels with POOL in Middlesboro in 2025 | Expedia.ca [Hotels in Middlesboro](https://expedia.ca/Middlesboro-Hotels.d8853.Travel-Guide-Hotels)[Vacation Rentals in Middlesboro](https://expedia.ca/Middlesboro-Vacation-Rentals.d8853.Travel-Guide-VacationRentals)[Flights to Middlesboro](https://expedia.ca/Cheap-Flights-To-Middlesboro.d8853.Travel-Guide-Flights)[Middlesboro Car Rentals](https://expedia.ca/Car-Rentals-In-Middlesboro.d8853.Car-Rental-Guide)[Middlesboro Vacation Packages](https://expedia.ca/Middlesboro.d8853.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/aaf95e2362319d0be23171c8a72261cf.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Alexis Wyrick # Find Hotels with a Pool in Middlesboro, KY from CA $100 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Middlesboro Hotels with a Pool Tonight [Sep 26 - Sep 27](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-09-26&endDate=2025-09-27&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 27 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-09-27&endDate=2025-09-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-09-26&endDate=2025-09-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-10-03&endDate=2025-10-05&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Middlesboro Hotels with a Pool ![Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/2000000/1110000/1109500/1109434/549f41ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, Balcony, Mountain View | Aerial view](https://images.trvl-media.com/lodging/2000000/1110000/1109500/1109434/d38a5bd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/2000000/1110000/1109500/1109434/4ec8d24c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1110000/1109500/1109434/4a64fadc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pine Mountain State Resort Park Pineville 9.0/10 Wonderful (620) "Great place to stay on a weekend trip" CA $110 CA $121 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Corbin-Hotels-Pine-Mountain-State-Resort-Park.h1109434.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/10000/300/279/b362fe26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/300/279/201264a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/300/279/4f0e0a80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Queen Beds, Non Smoking | Room amenity](https://images.trvl-media.com/lodging/1000000/10000/300/279/1f7ba691.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn by Wyndham Jellico - Tennessee State Line Jellico 7.2/10 Good (998) "The area, nice scenery " CA $88 CA $100 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Caryville-Hotels-Days-Inn-By-Wyndham-Jellico-Tennessee-State-Line.h279.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/1000000/70000/60900/60850/27ee2711.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/70000/60900/60850/d8f164b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/70000/60900/60850/2eaf3737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Mountain View](https://images.trvl-media.com/lodging/1000000/70000/60900/60850/2d181d81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Middlesboro by IHG Middlesboro 9.6/10 Exceptional (677) "Very clean and great breakfast. Staff is very helpful. " CA $169 CA $186 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Middlesboro-Hotels-Holiday-Inn-Express-Middlesboro.h60850.Hotel-Information) ![Business centre](https://images.trvl-media.com/lodging/1000000/20000/17100/17023/150349c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/17100/17023/93f0a861.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Barbourville 8.2/10 Very good (260) "Staff member who checked me in was very friendly and helpful. " CA $152 CA $172 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Corbin-Hotels-Best-Western-Wilderness-Trail-Inn.h17023.Hotel-Information) ![Double Room, Smoking](https://images.trvl-media.com/lodging/35000000/34980000/34978900/34978817/6bf5898c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Single Room, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/35000000/34980000/34978900/34978817/e0f53b15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34980000/34978900/34978817/cbceebb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Single Room, 1 Queen Bed, Smoking](https://images.trvl-media.com/lodging/35000000/34980000/34978900/34978817/df5282ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Boone Trail Inn Middlesboro 7.2/10 Good (101) "Everything was ok just needed more blankets on the bed….. A thin blanket isn’t enough! " CA $87 CA $120 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Middlesboro-Hotels-Boone-Trail-Inn.h34978817.Hotel-Information) ![Seasonal outdoor pool, open 10:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/15200/15146/c38450c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/15200/15146/c30cd65d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/15200/15146/e2e08685.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Snack bar](https://images.trvl-media.com/lodging/1000000/20000/15200/15146/5b2610cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Econo Lodge Middlesboro Middlesboro 7.2/10 Good (435) "We stayed here " CA $112 CA $123 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Middlesboro-Hotels-Econo-Lodge.h15146.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/70000000/69400000/69390100/69390006/a277b250.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/70000000/69400000/69390100/69390006/d57febbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave](https://images.trvl-media.com/lodging/70000000/69400000/69390100/69390006/bb8a8e6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/70000000/69400000/69390100/69390006/88c4c8c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Suburban Studios Middlesboro Middlesboro 8.0/10 Very good (59) "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! " CA $112 CA $123 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Middlesboro-Hotels-Suburban-Extended-Stay-Hotel.h69390006.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/17000/16941/94a0b136.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/20000/17000/16941/0451853f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/20000/17000/16941/43d53c9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/17000/16941/e1327cb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Harlan 8.6/10 Excellent (319) "Wonderful stay and amenities " CA $162 CA $183 total includes taxes & fees Oct 3 - Oct 4 [](https://www.expedia.ca/Harlan-Hotels-Quality-Inn.h16941.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/24000000/23250000/23240900/23240809/7f7a598a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/24000000/23250000/23240900/23240809/7b78ad82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/24000000/23250000/23240900/23240809/4cc09473.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/24000000/23250000/23240900/23240809/cf8d091b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Williamsburg by IHG Williamsburg 9.0/10 Wonderful (1004) "We really enjoyed our stay! " CA $174 CA $197 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Corbin-Hotels-Holiday-Inn-Express-Williamsburg.h23240809.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/17000000/16540000/16536400/16536329/32a090b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/17000000/16540000/16536400/16536329/55fb9b6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/17000000/16540000/16536400/16536329/fed88dd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/17000000/16540000/16536400/16536329/544d1b99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Woodlake Lodge Golf and Country Club Tazewell 9.4/10 Exceptional (141) "Gym was closed, restaurant was closed... pool was nice. Course is beautiful." CA $223 CA $250 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Morristown-Hotels-Woodlake-Lodge-Golf-And-Country-Club.h16536329.Hotel-Information) 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](https://expedia.ca/Hotel-Search?startDate=2025-10-11&endDate=2025-10-12®ionId=8853&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Middlesboro Hotel Reviews ![Pine Mountain State Resort Park](//images.trvl-media.com/lodging/2000000/1110000/1109500/1109434/75b8d155_y.jpg) ### Pine Mountain State Resort Park 10/10 Excellent "Wonderful staff" [](https://expedia.ca/Corbin-Hotels-Pine-Mountain-State-Resort-Park.h1109434.Hotel-Information) ![Days Inn by Wyndham Jellico - Tennessee State Line](//images.trvl-media.com/lodging/1000000/10000/300/279/b362fe26_y.jpg) ### Days Inn by Wyndham Jellico - Tennessee State Line 10/10 Excellent "Clean newly remodeled spacious room. Comfortable bed. Parked at our door. Quiet. Friendly staff. Comfortable tub. Hot water plentiful. Serene surroundings. Cute small town. Could use more lighting around mirror at the sink. Good value. Highly recommended." [](https://expedia.ca/Caryville-Hotels-Days-Inn-By-Wyndham-Jellico-Tennessee-State-Line.h279.Hotel-Information) ![Econo Lodge Middlesboro](//images.trvl-media.com/lodging/1000000/20000/15200/15146/853995b8_y.jpg) ### Econo Lodge Middlesboro 10/10 Excellent "Great" [](https://expedia.ca/Middlesboro-Hotels-Econo-Lodge.h15146.Hotel-Information) ![Quality Inn](//images.trvl-media.com/lodging/1000000/20000/17000/16941/b003bff0_y.jpg) ### Quality Inn 10/10 Excellent "Wonderful hotel. Friendly staff, well-maintained facilities, clean & comfy room. Nice hot breakfast." [](https://expedia.ca/Harlan-Hotels-Quality-Inn.h16941.Hotel-Information) ![Holiday Inn Express Middlesboro by IHG](//images.trvl-media.com/lodging/1000000/70000/60900/60850/3963de73_y.jpg) ### Holiday Inn Express Middlesboro by IHG 10/10 Excellent "Very clean and loved that Dove products were supplied" [](https://expedia.ca/Middlesboro-Hotels-Holiday-Inn-Express-Middlesboro.h60850.Hotel-Information) ![Super 8 by Wyndham Williamsburg](//images.trvl-media.com/lodging/1000000/10000/7000/6940/fe1198d1_y.jpg) ### Super 8 by Wyndham Williamsburg 10/10 Excellent "That it was clean, convenient, and quiet. Im from Toledo, Ohio and come here to Williamsburg to see my mom in the nursing home and this hotel was also affordable. " [](https://expedia.ca/Corbin-Hotels-Super-8-By-Wyndham-Williamsburg.h6940.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Middlesboro? > [Sleep Inn & Suites](https://www.expedia.ca/Middlesboro-Hotels-Sleep-Inn-Suites.h3929546.Hotel-Information): Offers buffet, an outdoor pool, and free self parking. [Holiday Inn Express Middlesboro by IHG](https://www.expedia.ca/Middlesboro-Hotels-Holiday-Inn-Express-Middlesboro.h60850.Hotel-Information): Provides continental, a seasonal outdoor pool, and free self parking. [Econo Lodge Middlesboro](https://www.expedia.ca/Middlesboro-Hotels-Econo-Lodge.h15146.Hotel-Information): Features free self parking, a seasonal outdoor pool, and complimentary wireless internet access. [Pine Mountain State Resort Park](https://www.expedia.ca/Corbin-Hotels-Pine-Mountain-State-Resort-Park.h1109434.Hotel-Information): Offers daily, an indoor pool, and free self parking. [Holiday Inn Express Williamsburg by IHG](https://www.expedia.ca/Corbin-Hotels-Holiday-Inn-Express-Williamsburg.h23240809.Hotel-Information): Features a full-service spa, a seasonal outdoor pool, and daily. ### 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. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Artemus Hotels](https://www.expedia.ca/Artemus-Hotels.d3000347263.Travel-Guide-Hotels) - [Cheap Hotels in Barbourville](https://www.expedia.ca/Barbourville-Hotels-Cheap-Hotels.0-0-d6267-tCheapHotels.Travel-Guide-Filter-Hotels) - [Barbourville Hotels](https://www.expedia.ca/Barbourville-Hotels.d6267.Travel-Guide-Hotels) - [Motels in Barbourville](https://www.expedia.ca/Barbourville-Motels.d6267-aaMotels.Travel-Guide-Accommodation) - [Bimble Hotels](https://www.expedia.ca/Bimble-Hotels.d3000347273.Travel-Guide-Hotels) - [Hotels near Black Mountain](https://www.expedia.ca/Black-Mountain-Hotels.0-l6091535-0.Travel-Guide-Filter-Hotels) - [Hotels near Boone's Ridge Wildlife Park](https://www.expedia.ca/Boones-Ridge-Wildlife-Park-Hotels.0-l814992773973426176-0.Travel-Guide-Filter-Hotels) - 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