Title: Book the Best Middlesboro Hotels with FREE PARKING 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 Free Parking in Middlesboro, KY from CA $101 - ![](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 Middlesboro Hotels with Free Parking Tonight [Nov 3 - Nov 4](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-11-03&endDate=2025-11-04&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 4 - Nov 5](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-11-04&endDate=2025-11-05&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-11-14&endDate=2025-11-16&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Middlesboro Hotels with Free Parking ![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) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1110000/1109500/1109434/4a64fadc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/2000000/1110000/1109500/1109434/a5889142.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) ### Pine Mountain State Resort Park Pineville 9.0/10 Wonderful (647) "Nice accommodations, staff very friendly and helpful. Mountain View’s from the restaurant and room were beautiful. A hidden gem." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ron CA $157 CA $173 total includes taxes & fees Nov 8 - Nov 9 [](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) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/300/279/d6ff4f38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn by Wyndham Jellico - Tennessee State Line Jellico 7.2/10 Good (1002) "All the staff were very helpful. The room had been newly renovated and was extremely clean. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) J. Roger CA $88 CA $101 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Caryville-Hotels-Days-Inn-By-Wyndham-Jellico-Tennessee-State-Line.h279.Hotel-Information) ![Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/114000000/113970000/113960300/113960224/85457286.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/114000000/113970000/113960300/113960224/bcb90117.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Double Beds, Non Smoking | Bathroom](https://images.trvl-media.com/lodging/114000000/113970000/113960300/113960224/176ec9e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113970000/113960300/113960224/68e298aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Imperial Inn by OYO Tazewell Tazewell 9.2/10 Wonderful (42) "Great hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tahir CA $89 CA $115 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Tazewell-Hotels-Imperial-Inn.h113960224.Hotel-Information) ![Double Room, Smoking](https://images.trvl-media.com/lodging/35000000/34980000/34978900/34978817/347cf131.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) ![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, Non Smoking](https://images.trvl-media.com/lodging/35000000/34980000/34978900/34978817/e0f53b15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Boone Trail Inn Middlesboro 7.2/10 Good (108) "Place was clean. AC worked good. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $87 CA $120 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Middlesboro-Hotels-Boone-Trail-Inn.h34978817.Hotel-Information) ![Standard Room](https://images.trvl-media.com/lodging/1000000/70000/60900/60850/3963de73.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/fba51913.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/70000/60900/60850/27ee2711.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Middlesboro by IHG Middlesboro 9.6/10 Exceptional (686) "Great breakfast. Room was spacious, clean and the dove products in the bathroom were nice. Great stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rachel CA $163 CA $179 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Middlesboro-Hotels-Holiday-Inn-Express-Middlesboro.h60850.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/4000000/3930000/3929600/3929546/1cf62fd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3930000/3929600/3929546/650307df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/4000000/3930000/3929600/3929546/29498a28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3930000/3929600/3929546/78cde3c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleep Inn & Suites Middlesboro Middlesboro 9.2/10 Wonderful (799) "Clean, super nice staff, bed comfortable " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kay CA $126 CA $139 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Middlesboro-Hotels-Sleep-Inn-Suites.h3929546.Hotel-Information) ![Standard Room, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/70000000/69400000/69390100/69390006/1f420a69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![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 (64) "Ideal spot for music festival!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) joseph CA $106 CA $117 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Middlesboro-Hotels-Suburban-Extended-Stay-Hotel.h69390006.Hotel-Information) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/15200/15146/c30cd65d.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) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/15200/15146/e2e08685.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Econo Lodge Middlesboro Middlesboro 7.2/10 Good (441) "Clean place with friendly staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $112 CA $123 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Middlesboro-Hotels-Econo-Lodge.h15146.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/17000/16941/b003bff0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/17000/16941/94a0b136.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) ![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) ### Quality Inn Harlan 8.6/10 Excellent (328) "The breakfast was great and the parking lot felt safe and had plenty of lighting. Overall a good stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $131 CA $148 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Harlan-Hotels-Quality-Inn.h16941.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 (263) "I recently stayed 2 nights here. My stay was wonderful. Everything was clean and fresh. I actually felt at home here. Great job!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tonya CA $137 CA $156 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Corbin-Hotels-Best-Western-Wilderness-Trail-Inn.h17023.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=2025-11-17&endDate=2025-11-18®ionId=8853&adults=2&amenities=FREE_PARKING&sort=RECOMMENDED&openPlayBack=true) ## Top Middlesboro Hotel Reviews ![Sleep Inn & Suites](//images.trvl-media.com/lodging/4000000/3930000/3929600/3929546/1cf62fd0_y.jpg) ### Sleep Inn & Suites 10/10 Excellent "Excellent breakfast" [](https://expedia.ca/Middlesboro-Hotels-Sleep-Inn-Suites.h3929546.Hotel-Information) ![Econo Lodge Middlesboro](//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) ![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 "The staff were extremely nice and friendly. The Cabin was very clean, warm and had a full equipped kitchen. I would definitely recommend Pine Mountain State Park Resort to my friends. " [](https://expedia.ca/Corbin-Hotels-Pine-Mountain-State-Resort-Park.h1109434.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 "Great " [](https://expedia.ca/Corbin-Hotels-Super-8-By-Wyndham-Williamsburg.h6940.Hotel-Information) ![Rodeway Inn](//images.trvl-media.com/lodging/9000000/8450000/8445600/8445506/b7b25f30_y.jpg) ### Rodeway Inn 10/10 Excellent "pretty safe " [](https://expedia.ca/Harlan-Hotels-Mount-Aire-Motel.h8445506.Hotel-Information) ![Quality Inn](//images.trvl-media.com/lodging/1000000/20000/17000/16941/b003bff0_y.jpg) ### Quality Inn 10/10 Excellent "I was visiting family in the Harlan area. I really liked this motel, convenient, quiet, safe and the breakfast was great. I would not hesitate to stay there again. " [](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 "Great breakfast. Room was spacious, clean and the dove products in the bathroom were nice. Great stay. " [](https://expedia.ca/Middlesboro-Hotels-Holiday-Inn-Express-Middlesboro.h60850.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) ![Quality Inn](//images.trvl-media.com/lodging/1000000/20000/17100/17023/150349c9_y.jpg) ### 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!!!" [](https://expedia.ca/Corbin-Hotels-Best-Western-Wilderness-Trail-Inn.h17023.Hotel-Information) ## 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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