Title: Middlesboro B&B: Find the Best Bed and Breakfast from CA $211 | 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) ![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.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 prices for these dates Next weekend [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) 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&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2026-02-20&endDate=2026-02-22&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2026-03-20&endDate=2026-03-22&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Middlesboro bed & breakfast ![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) ![Room (RV Campsite, 24' Electric) | Exterior](https://images.trvl-media.com/lodging/10000000/9090000/9083300/9083253/4d8c852a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, Ensuite (Studio 603) | Bathroom](https://images.trvl-media.com/lodging/10000000/9090000/9083300/9083253/e9deeab2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, Ensuite (Studio 603)](https://images.trvl-media.com/lodging/10000000/9090000/9083300/9083253/4637aef1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Olde Mill Inn Bed & Breakfast [](https://www.expedia.ca/Cumberland-Gap-Hotels-The-Olde-Mill-Inn-Bed-Breakfast.h9083253.Hotel-Information) Cumberland Gap 9.2/10 Wonderful (427 reviews) "Staff was very communicative, room was clean with all necessary amenities. Good location. Comfy beds. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer CA $187 CA $211 total includes taxes & fees Jan 20 - Jan 21 [](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=2026-02-02&endDate=2026-02-03®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 ![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) ![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 "Breakfast was great. " [](https://expedia.ca/Corbin-Hotels-Holiday-Inn-Express-Williamsburg.h23240809.Hotel-Information) ![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 "Clean room staff was kind the lodge for dinner or lunch is our favorite " [](https://expedia.ca/Corbin-Hotels-Pine-Mountain-State-Resort-Park.h1109434.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 "Room was SPOTLESS. So clean and so nice and soooo affordable! Front desk lady was so nice and helpful as well. Will be staying here again on our travels. " [](https://expedia.ca/Caryville-Hotels-Days-Inn-By-Wyndham-Jellico-Tennessee-State-Line.h279.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) ![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 "Beautiful place, very relaxing. The property has EVERYTHING you might need to entertain. Extremely impress with the space. We were 17 and had plenty of space. Loved the 2 kitchens, it made it so much easier for the big group. Definitely we want to come back, totally worth it!!!" [](https://expedia.ca/La-Follette-Hotels-Family-Affair.h33075394.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) ![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 "Staff was very communicative, room was clean with all necessary amenities. Good location. Comfy beds. " [](https://expedia.ca/Cumberland-Gap-Hotels-The-Olde-Mill-Inn-Bed-Breakfast.h9083253.Hotel-Information) ## Find out more about Middlesboro ## Middlesboro B&B information | Number of reviews | 178 | | ----------------- | ------- | | Accommodation | 1 B&B | | Lowest Price | CA $211 | | Highest Price | CA $211 | ## 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 - 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) - 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