Title: Book the Best Hotels with POOL in Harlan in 2025 | Expedia.ca [Harlan Travel Guide](https://expedia.ca/Harlan.dx8279)[Hotels in Harlan](https://expedia.ca/Harlan-Hotels.d8279.Travel-Guide-Hotels)[Vacation Rentals in Harlan](https://expedia.ca/Harlan-Vacation-Rentals.d8279.Travel-Guide-VacationRentals)[Flights to Harlan](https://expedia.ca/Cheap-Flights-To-Harlan.d8279.Travel-Guide-Flights)[Harlan Car Rentals](https://expedia.ca/Car-Rentals-In-Harlan.d8279.Car-Rental-Guide)[Harlan Vacation Packages](https://expedia.ca/Harlan.d8279.Destination-Travel-Guides) ![Early fall colors at High Rock atop Pine Mountain in Kentucky.](https://images.trvl-media.com/place/8279/3306c596-91b1-408c-975c-10276bc9d15a.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Harlan, KY - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](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) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Harlan Hotels with a Pool Tonight [Nov 22 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=8279&startDate=2025-11-22&endDate=2025-11-23&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 23 - Nov 24](https://www.expedia.ca/Hotel-Search?regionId=8279&startDate=2025-11-23&endDate=2025-11-24&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=8279&startDate=2025-11-28&endDate=2025-11-30&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=8279&startDate=2025-12-05&endDate=2025-12-07&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Harlan 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) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1110000/1109500/1109434/4a64fadc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor wedding area](https://images.trvl-media.com/lodging/2000000/1110000/1109500/1109434/75b8d155.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pine Mountain State Resort Park Pineville 9.0/10 Wonderful (660) "Staff were amazing! Very unique experience in the cottage and the fireplace was really special highly recommended!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrew CA $138 CA $152 total includes taxes & fees Nov 26 - Nov 27 [](https://www.expedia.ca/Corbin-Hotels-Pine-Mountain-State-Resort-Park.h1109434.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/70000/60900/60850/2eaf3737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Middlesboro by IHG Middlesboro 9.6/10 Exceptional (690) "Clean hotel, good breakfast options." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Harold CA $158 CA $174 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Middlesboro-Hotels-Holiday-Inn-Express-Middlesboro.h60850.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) ![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) ![Single Room, 1 Queen Bed, Smoking](https://images.trvl-media.com/lodging/35000000/34980000/34978900/34978817/2a62b61c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Boone Trail Inn Middlesboro 7.2/10 Good (109) "Place was clean. AC worked good. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $88 CA $121 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Middlesboro-Hotels-Boone-Trail-Inn.h34978817.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) ![Fridge, microwave](https://images.trvl-media.com/lodging/70000000/69400000/69390100/69390006/bb8a8e6f.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) ![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 (65) "Didn't stay as we found a better location in Cumberland Gap. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alan CA $107 CA $118 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Middlesboro-Hotels-Suburban-Extended-Stay-Hotel.h69390006.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) ![Snack bar](https://images.trvl-media.com/lodging/1000000/20000/15200/15146/5b2610cc.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) ![Standard Room, 2 Double Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/20000/15200/15146/853995b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Econo Lodge Middlesboro Middlesboro 7.2/10 Good (442) "Clean place with friendly staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $106 CA $117 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Middlesboro-Hotels-Econo-Lodge.h15146.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=2025-12-07&endDate=2025-12-08®ionId=8279&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AFFINITY_BF_PROMO_8279) ## Top Harlan Hotel Reviews ![Pine Mountain State Resort Park](https://images.trvl-media.com/lodging/2000000/1110000/1109500/1109434/75b8d155_y.jpg) ### Pine Mountain State Resort Park 10/10 Excellent "We have been to a lot of State Parks over the years and this one might be the best. Great views. The staff and service were amazing, and our cabin was nice and clean. We ate breakfast and dinner at the lodge several times and it was always fantastic. The alcohol menu is really nice, plenty of variety and reasonably priced. They offer more amenities than other parks like borrowing a fishing pole and tackle box for the lake. You can also borrow board games from the game room to take to your room/cabin. The game room also has a ping pong table, a table-size Connect4 game and other cool things. Pet friendly. The hiking trails were clear and labeled well with plenty of signs. We will be visiting again." [](https://expedia.ca/Corbin-Hotels-Pine-Mountain-State-Resort-Park.h1109434.Hotel-Information) ![Quality Inn](https://images.trvl-media.com/lodging/1000000/20000/17000/16941/b003bff0_y.jpg) ### Quality Inn 10/10 Excellent "The staff was really friendly and the beds were very comfortable. " [](https://expedia.ca/Harlan-Hotels-Quality-Inn.h16941.Hotel-Information) ![Holiday Inn Express Middlesboro by IHG](https://images.trvl-media.com/lodging/1000000/70000/60900/60850/3963de73_y.jpg) ### Holiday Inn Express Middlesboro by IHG 10/10 Excellent "Very comfortable and clean." [](https://expedia.ca/Middlesboro-Hotels-Holiday-Inn-Express-Middlesboro.h60850.Hotel-Information) ![Econo Lodge Middlesboro](https://images.trvl-media.com/lodging/1000000/20000/15200/15146/853995b8_y.jpg) ### Econo Lodge Middlesboro 10/10 Excellent "Clean rooms" [](https://expedia.ca/Middlesboro-Hotels-Econo-Lodge.h15146.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Harlan? > [Quality Inn](https://www.expedia.ca/Harlan-Hotels-Quality-Inn.h16941.Hotel-Information): Features sun loungers, a pool, and kitchens. [Rodeway Inn](https://www.expedia.ca/Harlan-Hotels-Mount-Aire-Motel.h8445506.Hotel-Information): Provides free self parking, a seasonal outdoor pool, and complimentary wireless internet access. [Harlan, KY Modern Private Guesthouse 302 Historic Downtown (Vela's Villas)](https://www.expedia.ca/Harlan-Hotels-Harlan.h74587798.Hotel-Information): Offers continental, a seasonal outdoor pool, and free self parking. [Harlan, KY GuestHouse 300 Vacation/Weddings/Events (Cole Mansion)](https://www.expedia.ca/Harlan-Hotels-Harlan.h74587893.Hotel-Information): Offers buffet, an outdoor pool, and free self parking. [Beautiful Loft in the Woods](https://www.expedia.ca/Harlan-Hotels-Beautiful-Loft-In-The-Woods.h109452271.Hotel-Information): Features daily, a seasonal outdoor pool, and free self parking. ### What is there to see and do in Harlan? > The picturesque setting of Cumberland River showcases the area's natural beauty. Discover sights such as Cumberland Gap National Historical Park and Smith Recreation Area Beach during your stay. ### When is the best time to book a hotel with a pool in Harlan? > You may want to consider a place to stay that has an outdoor pool if you're planning to visit Harlan in the hottest months of July, August, or June when the average temp is 71°F. 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