Title: Book the Best HISTORIC Hotels 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 Historic Hotels in Middlesboro, KY from CA $117 - ![](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 Historic Hotels Tonight [Nov 3 - Nov 4](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-11-03&endDate=2025-11-04&adults=2&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&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&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&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Middlesboro Historic Hotels We don't have any properties that match your exact search [See all properties in Middlesboro](https://expedia.ca/Hotel-Search?startDate=2025-11-17&endDate=2025-11-18®ionId=8853&adults=2) ## Recommended hotels in Middlesboro ![Standard Room](https://images.trvl-media.com/lodging/1000000/70000/60900/60850/3963de73.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/70000/60900/60850/fba51913.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 (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) ![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, 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 (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, 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) ![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) ![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 (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) ![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) ![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) ### 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, 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) ![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 (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) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113130000/113124900/113124803/a21e0b91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113130000/113124900/113124803/6668ab96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/114000000/113130000/113124900/113124803/3ea56b6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113130000/113124900/113124803/2b33c7e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky, Middlesboro 10/10 Exceptional (20) "Our group had a wonderful time staying at Uncle Ernie's! Everything was neat, tidy, and felt like home. We definitely will be back next time we are in the area!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Savannah P. CA $167 CA $326 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Middlesboro-Hotels-Cozy-2-Bedroom-Lustron-Home-Located-In-Middlesboro.h113124803.Hotel-Information) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/111000000/110870000/110864800/110864705/c11669c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/111000000/110870000/110864800/110864705/a0ca2385.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/111000000/110870000/110864800/110864705/cde6bef3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110870000/110864800/110864705/439f4fac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals. Middlesboro 9.2/10 Wonderful (5) "We enjoyed our stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emily S. CA $178 CA $434 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Middlesboro-Hotels-Charming-3-Bedroom-House-In-The-Crater-City-Near-State-Parks.h110864705.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/120000000/119650000/119642400/119642383/2f2cc548.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/120000000/119650000/119642400/119642383/d0cfcd54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/120000000/119650000/119642400/119642383/c9fc43d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/120000000/119650000/119642400/119642383/509d4ba3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Welcoming 3-bedroom house with AC in charming Middlesboro Middlesboro CA $166 CA $342 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Middlesboro-Hotels-Welcoming-3-Bedroom-House-With-AC-In-Charming-Middlesboro.h119642383.Hotel-Information) ![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117740000/117736400/117736392/w2000h2797x0y0-ff41d957.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117740000/117736400/117736392/a482c2a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117740000/117736400/117736392/w1997h2800x0y0-b5dc7fe0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117740000/117736400/117736392/4228b014.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU Middlesboro CA $465 CA $762 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Middlesboro-Hotels-Spacious-Renovated-Ranch-Retreat-Near-Tackett-Creek-Cumberland-Gap-Park.h117736392.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) ![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) 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&specialized_stays_group_explore=historic_property&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) ![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) ## Frequently asked questions ### What should a history buff expect from a stay in Middlesboro? > A trip to the historical places in Middlesboro is probably first on your sightseeing itinerary. Why not appreciate the mountain landscape during your visit? ### How many historical hotels will I find in Middlesboro? > In Middlesboro, there are 10 hotel accommodations bookable on Expedia but not many designated as historic hotels. ### What are the top historical sites and other places to visit in Middlesboro? > Landmarks like Cumberland Gap National Historical Park and Bell County Historical Society Museum in Middlesboro might be worth a visit. A couple of additional sights to add to your agenda are Middlesboro Country Club and Middlesboro Mall. ### What is a historic hotel like in Middlesboro? > By choosing a historic hotel, you can enjoy a vacation in a building that has an official historic designation. A stately home, palace or even a lodge, old police station, or skyscraper can be transformed into a historic hotel as long as it has special significance. Traditional architecture and period features are typically preserved in the guestrooms or communal spaces of these historic hotels in Middlesboro, bringing the history to life. ### What is the difference between a historic hotel and a heritage hotel? > "Heritage hotel" is more common in Asia and Europe, while "historic hotel" is more common in the U.S. overall though the terms are similar. The architecture and actual building of historic hotels are generally the most significant aspect. For a heritage hotel, mainly, it's cultural value along with how it inspired the community. ### Do historic hotels in Middlesboro have modern facilities? > Hotel interiors feature the modern conveniences and safety features you've come to expect, but every effort is made to preserve the historic aspects and traditions. Smart TVs, WiFi, updated bathroom facilities, and the amenities found in most hotels will also be available in a historic hotel. Rest assured that when you select a historic hotel in Middlesboro, you won't find a place that's uncomfortable or rundown. ## 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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