Title: Book the Best BUSINESS Hotels in Middlesboro in 2026 | 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) ![#Adventure #CumberlandGap #High #Trees #Highway](https://images.trvl-media.com/place/8853/b202c2ca-a802-49c4-b0c7-db992700a740.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Alexis Wyrick ![](https://images.trvl-media.com/place/8853/b202c2ca-a802-49c4-b0c7-db992700a740.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 Business Hotels Tonight [Jan 25 - Jan 26](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2026-01-25&endDate=2026-01-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=business_friendly) Tomorrow [Jan 26 - Jan 27](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2026-01-26&endDate=2026-01-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=business_friendly) Next weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=business_friendly) In two weeks [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=business_friendly) ## Our top choices for Middlesboro business-friendly hotels ![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/1000000/70000/60900/60850/2eaf3737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/70000/60900/60850/e6d48611.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/70000/60900/60850/ab02f897.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Middlesboro by IHG [](https://www.expedia.ca/Middlesboro-Hotels-Holiday-Inn-Express-Middlesboro.h60850.Hotel-Information) Middlesboro 9.6/10 Exceptional (700 reviews) "Only stayed one night but the hotel was quiet, considering the amount of people that seemed to be there, very clean and the breakfast was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin CA $171 CA $189 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Middlesboro-Hotels-Holiday-Inn-Express-Middlesboro.h60850.Hotel-Information) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/4000000/3930000/3929600/3929546/86beaca2.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) ![Exterior](https://images.trvl-media.com/lodging/4000000/3930000/3929600/3929546/5f493061.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 [](https://www.expedia.ca/Middlesboro-Hotels-Sleep-Inn-Suites.h3929546.Hotel-Information) Middlesboro 9.2/10 Wonderful (819 reviews) "Room was clean and comfortable. Staff was courteous. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tommy CA $128 CA $141 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Middlesboro-Hotels-Sleep-Inn-Suites.h3929546.Hotel-Information) ![Suite, 2 Queen Beds, Non Smoking | Bathroom](https://images.trvl-media.com/lodging/1000000/10000/300/279/ad47702e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/300/279/c209de71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 9 AM to 10 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/300/279/85bd7419.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/300/279/6adc7a76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn by Wyndham Jellico - Tennessee State Line [](https://www.expedia.ca/Caryville-Hotels-Days-Inn-By-Wyndham-Jellico-Tennessee-State-Line.h279.Hotel-Information) Jellico 7.2/10 Good (1,001 reviews) "Nice location, nice room, friendly staff and recent remodeling rooms " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ashley CA $91 CA $104 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Caryville-Hotels-Days-Inn-By-Wyndham-Jellico-Tennessee-State-Line.h279.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/17000000/16540000/16536400/16536329/544d1b99.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) ![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) ### Woodlake Lodge Golf and Country Club [](https://www.expedia.ca/Morristown-Hotels-Woodlake-Lodge-Golf-And-Country-Club.h16536329.Hotel-Information) Tazewell 9.4/10 Exceptional (143 reviews) "Friendly staff and clean accommodations " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rachel CA $178 CA $200 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Morristown-Hotels-Woodlake-Lodge-Golf-And-Country-Club.h16536329.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) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/20000/17000/16941/511d1b15.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) ![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 [](https://www.expedia.ca/Harlan-Hotels-Quality-Inn.h16941.Hotel-Information) Harlan 8.6/10 Excellent (344 reviews) "Room was nice and clean, staff very courteous, breakfast very good." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gary CA $128 CA $145 total includes taxes & fees Feb 1 - Feb 2 [](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=2026-02-08&endDate=2026-02-09®ionId=8853&adults=2&travelerType=business_friendly&sort=RECOMMENDED&openPlayBack=true) ## Top Middlesboro Hotel Reviews ![The Olde Mill Inn Bed & Breakfast](https://images.trvl-media.com/lodging/10000000/9090000/9083300/9083253/d129b690_y.jpg) ### The Olde Mill Inn Bed & Breakfast 10/10 Excellent "The staff was excellent. They are wonderful people. They made sure everything was perfect. We enjoyed having breakfast with the other guests. They addressed any allergy concerns and tailored your breakfast for all. I would recommend this bed and breakfast it is the best one we have ever stayed at" [](https://expedia.ca/Cumberland-Gap-Hotels-The-Olde-Mill-Inn-Bed-Breakfast.h9083253.Hotel-Information) ![Days Inn by Wyndham Jellico - Tennessee State Line](https://images.trvl-media.com/lodging/1000000/10000/300/279/b362fe26_y.jpg) ### Days Inn by Wyndham Jellico - Tennessee State Line 10/10 Excellent "It was clean" [](https://expedia.ca/Caryville-Hotels-Days-Inn-By-Wyndham-Jellico-Tennessee-State-Line.h279.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 "Clean room" [](https://expedia.ca/Middlesboro-Hotels-Holiday-Inn-Express-Middlesboro.h60850.Hotel-Information) ![Sleep Inn & Suites Middlesboro](https://images.trvl-media.com/lodging/4000000/3930000/3929600/3929546/1cf62fd0_y.jpg) ### Sleep Inn & Suites Middlesboro 10/10 Excellent "Room and all public areas very clean Breakfast was great Elevator was down but staff went above and beyond to accommodate any inconvenience including discounts arranged with local restaurants. Completely unnecessary but very appreciated. We will stay there again" [](https://expedia.ca/Middlesboro-Hotels-Sleep-Inn-Suites.h3929546.Hotel-Information) ![Super 8 by Wyndham Williamsburg](https://images.trvl-media.com/lodging/1000000/10000/7000/6940/fe1198d1_y.jpg) ### Super 8 by Wyndham Williamsburg 10/10 Excellent "Clean room, friendly- helpful staff " [](https://expedia.ca/Corbin-Hotels-Super-8-By-Wyndham-Williamsburg.h6940.Hotel-Information) ![Quality Inn](https://images.trvl-media.com/lodging/1000000/20000/17000/16941/b003bff0_y.jpg) ### Quality Inn 10/10 Excellent "They were kind check out and in was swift and smooth and the room was well kept and clean and bed was comfy " [](https://expedia.ca/Harlan-Hotels-Quality-Inn.h16941.Hotel-Information) ## Frequently asked questions ### How much do business-friendly hotels in Middlesboro cost? ### What are the best business-friendly hotels in Middlesboro? ### How many business-friendly hotels are there in Middlesboro? ### What are the best cheap business-friendly hotels in Middlesboro? ### Are there any family-friendly hotels in Middlesboro that are also business friendly? ### Why book your business-friendly hotel in Middlesboro with Expedia? ### How can I find cheap business-friendly hotels in Middlesboro? ### What is there to do in Middlesboro near my business-friendly hotel? ## Explore a world of travel with Expedia - 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