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 [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-10-13&endDate=2025-10-14&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-10-14&endDate=2025-10-15&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-10-24&endDate=2025-10-26&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Middlesboro Hotels with Free Parking ![Exterior](https://images.trvl-media.com/lodging/24000000/23250000/23240900/23240809/7b78ad82.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) ![Indoor pool](https://images.trvl-media.com/lodging/24000000/23250000/23240900/23240809/7f7a598a.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) ### Holiday Inn Express Williamsburg by IHG Williamsburg 9.0/10 Wonderful (1007) "We really enjoyed our stay! " CA $140 CA $158 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Corbin-Hotels-Holiday-Inn-Express-Williamsburg.h23240809.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/1000000/70000/60900/60850/2eaf3737.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) ### Holiday Inn Express Middlesboro by IHG Middlesboro 9.6/10 Exceptional (681) "Clean room Great breakfast Staff friendly and helpful " CA $165 CA $182 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Middlesboro-Hotels-Holiday-Inn-Express-Middlesboro.h60850.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) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/300/279/d6ff4f38.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) ![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) ### Days Inn by Wyndham Jellico - Tennessee State Line Jellico 7.2/10 Good (1003) "The area, nice scenery " CA $88 CA $101 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Caryville-Hotels-Days-Inn-By-Wyndham-Jellico-Tennessee-State-Line.h279.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) ![Suite, 2 Queen Beds, Accessible, Non Smoking](https://images.trvl-media.com/lodging/4000000/3930000/3929600/3929546/80a66b59.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 9.2/10 Wonderful (787) "Great stay. Good breakfast. Friendly staff. Fabulous coffee!" CA $131 CA $144 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Middlesboro-Hotels-Sleep-Inn-Suites.h3929546.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) ![Exterior](https://images.trvl-media.com/lodging/114000000/113970000/113960300/113960224/68e298aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/114000000/113970000/113960300/113960224/11021c25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Imperial Inn by OYO Tazewell Tazewell 9.2/10 Wonderful (35) "Great hotel" CA $80 CA $104 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Tazewell-Hotels-Imperial-Inn.h113960224.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) ![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) ### Econo Lodge Middlesboro Middlesboro 7.2/10 Good (437) "We stayed here " CA $118 CA $131 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Middlesboro-Hotels-Econo-Lodge.h15146.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) ![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) ![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 (106) "The man was extra friendly and gave me two bottles of water free of charge." CA $87 CA $120 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Middlesboro-Hotels-Boone-Trail-Inn.h34978817.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) ![Exterior](https://images.trvl-media.com/lodging/70000000/69400000/69390100/69390006/88c4c8c9.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) ### Suburban Studios Middlesboro Middlesboro 8.0/10 Very good (61) "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 $106 CA $117 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Middlesboro-Hotels-Suburban-Extended-Stay-Hotel.h69390006.Hotel-Information) ![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) ![Interior entrance](https://images.trvl-media.com/lodging/2000000/1110000/1109500/1109434/4ec8d24c.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) ### Pine Mountain State Resort Park Pineville 9.0/10 Wonderful (632) "Great views, and wonderful trails, and pet-friendly." CA $106 CA $116 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Corbin-Hotels-Pine-Mountain-State-Resort-Park.h1109434.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) ![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) ![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) ### Quality Inn Harlan 8.6/10 Excellent (323) "Wonderful stay and amenities " CA $137 CA $155 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Harlan-Hotels-Quality-Inn.h16941.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=2025-10-27&endDate=2025-10-28®ionId=8853&adults=2&amenities=FREE_PARKING&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 "Great views, and wonderful trails, and pet-friendly." [](https://expedia.ca/Corbin-Hotels-Pine-Mountain-State-Resort-Park.h1109434.Hotel-Information) ![Sleep Inn & Suites](//images.trvl-media.com/lodging/4000000/3930000/3929600/3929546/1cf62fd0_y.jpg) ### Sleep Inn & Suites 10/10 Excellent "We only stayed on night here on a quick trip to Colorado. Our room was clean, quiet, & comfy with nice bedding & towels. We liked the security of the facility. My husband wasn’t feeling well and when I started to take his breakfast to our room, the staff gave me a nice box to carry it in. They were friendly & helpful. The breakfast was good. " [](https://expedia.ca/Middlesboro-Hotels-Sleep-Inn-Suites.h3929546.Hotel-Information) ![Quality Inn](//images.trvl-media.com/lodging/1000000/20000/17000/16941/b003bff0_y.jpg) ### Quality Inn 10/10 Excellent "Fabulous staff and service" [](https://expedia.ca/Harlan-Hotels-Quality-Inn.h16941.Hotel-Information) ![Rodeway Inn](//images.trvl-media.com/lodging/9000000/8450000/8445600/8445506/b7b25f30_y.jpg) ### Rodeway Inn 8/10 Good "It is a simple but decent room. " [](https://expedia.ca/Harlan-Hotels-Mount-Aire-Motel.h8445506.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 "Clean room Great breakfast Staff friendly and helpful " [](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 "Ok" [](https://expedia.ca/Corbin-Hotels-Super-8-By-Wyndham-Williamsburg.h6940.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) ## 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) - 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