Title: Middlesboro B&B: Find the Best Bed and Breakfast from CA $212 | 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 # Find a Bed and Breakfast in Middlesboro from CA $212 - ![](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 prices for these dates Next weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-12-12&endDate=2025-12-14&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2026-01-30&endDate=2026-02-01&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Middlesboro B&B ![Suite, Accessible, Ensuite (Thomas Walker Annex)](https://images.trvl-media.com/lodging/10000000/9090000/9083300/9083253/d129b690.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite, Ensuite (a The Suite)](https://images.trvl-media.com/lodging/10000000/9090000/9083300/9083253/ff3382f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/10000000/9090000/9083300/9083253/78c6bb28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite, Ensuite (a The Suite)](https://images.trvl-media.com/lodging/10000000/9090000/9083300/9083253/5d5e1e35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Olde Mill Inn Bed & Breakfast Cumberland Gap 9.0/10 Wonderful (425) "Nice place in historic Cumberland Gap, walkable to hiking trail and pave local trail. The room is spacious, very clean, and comfortable bed. Homemade breakfast was delicious." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ry CA $187 CA $212 total includes taxes & fees Dec 5 - Dec 6 [](https://www.expedia.ca/Cumberland-Gap-Hotels-The-Olde-Mill-Inn-Bed-Breakfast.h9083253.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=2025-12-18&endDate=2025-12-19®ionId=8853&adults=2&lodging=BED_AND_BREAKFAST&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FMiddlesboro-Bed-And-Breakfast.d8853-aaBedAndBreakfast.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FMiddlesboro-Bed-And-Breakfast.d8853-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Middlesboro 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 "The staff here is amazing. Everyone was really nice and helpful:)" [](https://expedia.ca/Corbin-Hotels-Pine-Mountain-State-Resort-Park.h1109434.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 "Entire facility was spotless. Great staff. Breakfast was a normal hotel breakfast but was well organized and stocked. Didn’t feel like a gross buffet as it does at some hotels. " [](https://expedia.ca/Middlesboro-Hotels-Sleep-Inn-Suites.h3929546.Hotel-Information) ![Quality Inn](https://images.trvl-media.com/lodging/1000000/20000/17000/16941/b003bff0_y.jpg) ### Quality Inn 10/10 Excellent "Nice." [](https://expedia.ca/Harlan-Hotels-Quality-Inn.h16941.Hotel-Information) ![Family Affair, room 4 30, 15 Beds, 2 FULL Kitchens!!! Huge dock w 2 boat slips](https://images.trvl-media.com/lodging/34000000/33080000/33075400/33075394/87720b5d_y.jpg) ### Family Affair, room 4 30, 15 Beds, 2 FULL Kitchens!!! Huge dock w 2 boat slips 10/10 Excellent "Our family had the most amazing vacation at Family Affair home!! There is so much space. We had more than enough space for our family. The bedrooms are all spacious. There is so much to do that we hardly ever left the house. With 2 kitchens and dining areas we had everything we needed for our family chef to do his thing. The kids had a blast playing and running around the area hiking and exploring.We will be back in the summer time and take a trip to the jumping bridge!!The double decks on the boat dock was awesome for sitting and enjoying the beautiful views!" [](https://expedia.ca/La-Follette-Hotels-Family-Affair.h33075394.Hotel-Information) ![Holiday Inn Express Williamsburg by IHG](https://images.trvl-media.com/lodging/24000000/23250000/23240900/23240809/7b78ad82_y.jpg) ### Holiday Inn Express Williamsburg by IHG 10/10 Excellent "Every part of this hotel was outstanding for travelers such as us" [](https://expedia.ca/Corbin-Hotels-Holiday-Inn-Express-Williamsburg.h23240809.Hotel-Information) ![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 "Very clean room, fantastic pieces inside with lots of history and a magnificent breakfast!!" [](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 "We did not visit the pool,but it looked nice. Staff was very friendly and helpful. Especially the front desk people. Our housekeeper was very helpful. Also,very convenient to the highway." [](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 "Very comfortable and clean." [](https://expedia.ca/Middlesboro-Hotels-Holiday-Inn-Express-Middlesboro.h60850.Hotel-Information) ![Rodeway Inn](https://images.trvl-media.com/lodging/9000000/8450000/8445600/8445506/b7b25f30_y.jpg) ### Rodeway Inn 10/10 Excellent "Clean and staff was good The bathroom is putting out a bad smell like it was from the septic and we tried three different microwaves that did not work that was my only complaint" [](https://expedia.ca/Harlan-Hotels-Mount-Aire-Motel.h8445506.Hotel-Information) ## Find out more about Middlesboro ## Middlesboro B&B information | Number of reviews | 177 | | ----------------- | ------- | | Accommodation | 1 B&B | | Lowest Price | CA $212 | | Highest Price | CA $212 | ## Frequently asked questions ### Searching for B&Bs in Middlesboro? ### How do you know if a B&B is the right choice for your stay? ### What are the best bed and breakfasts in Middlesboro? ### When is the best time to book my B&B in Middlesboro? ### What is there to do in Middlesboro? ## Explore a world of travel with Expedia - 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