Title: Middlesboro B&B: Find the Best Bed and Breakfast from CA $213 | 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 a Bed and Breakfast in Middlesboro from CA $213 ![](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 [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [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) ## 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) ![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) ![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) ### The Olde Mill Inn Bed & Breakfast Cumberland Gap 9.0/10 Wonderful (420) "loved the historical setting, walking distance to shops, parks, hiking trails." CA $188 CA $213 total includes taxes & fees Oct 19 - Oct 20 [](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=2025-10-27&endDate=2025-10-28®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](//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) ![Holiday Inn Express Williamsburg by IHG](//images.trvl-media.com/lodging/24000000/23250000/23240900/23240809/7b78ad82_y.jpg) ### Holiday Inn Express Williamsburg by IHG 10/10 Excellent "Staff were amazing. Everything was very clean. Would certainly stay again. " [](https://expedia.ca/Corbin-Hotels-Holiday-Inn-Express-Williamsburg.h23240809.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) ![Beautiful Norris Lake Front A-Frame with Private Dock in Speedwell, Tn .](//images.trvl-media.com/lodging/67000000/66940000/66936200/66936119/58b13863_y.jpg) ### Beautiful Norris Lake Front A-Frame with Private Dock in Speedwell, Tn . 10/10 Excellent "Best ever will be back" [](https://expedia.ca/Speedwell-Hotels-Beautiful-Norris-Lake-Front-A-Frame-With-Private-Dock-And-Jet-Skit-Lift.h66936119.Hotel-Information) ![Boone Trail Inn](//images.trvl-media.com/lodging/35000000/34980000/34978900/34978817/347cf131_y.jpg) ### Boone Trail Inn 10/10 Excellent "Fine." [](https://expedia.ca/Middlesboro-Hotels-Boone-Trail-Inn.h34978817.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) ## Find out more about Middlesboro ## Middlesboro B&B information | Number of reviews | 172 | | --- | --- | | Accommodation | 1 B&B | | Lowest Price | CA $213 | | Highest Price | CA $213 | ## Frequently asked questions ### Searching for B&Bs in Middlesboro? > If you're looking for something a little more offbeat than your standard hotel experience, a stay at a bed and breakfast could be a great option for your getaway. If you're interested in playing some golf on your trip, Middlesboro Country Club is a good spot to tee off. ### How do you know if a B&B is the right choice for your stay? > With attentive service, opportunities to mingle with other guests, and breakfast served on site, B&Bs all have a truly one-of-a-kind environment. ### What are the best bed and breakfasts in Middlesboro? > Below is a B&B in the area: [The Olde Mill Inn Bed & Breakfast](https://www.expedia.ca/Cumberland-Gap-Hotels-The-Olde-Mill-Inn-Bed-Breakfast.h9083253.Hotel-Information): 8 rooms. 2.7 mi (4.4 km) from the heart of Middlesboro. ### When is the best time to book my B&B in Middlesboro? > When you're dreaming of a stay in Middlesboro, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 40°F. Average annual precipitation for Middlesboro is 62 inches. ### What is there to do in Middlesboro? > When you want to explore some things to do in town, Middlesboro Mall and Cumberland Gap National Historical Park are some notable sights to visit. 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