Title: Middlesboro B&B: Find the Best Bed and Breakfast from CA $320 | 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) ![mountain view](https://images.trvl-media.com/place/8853/4dcad675-90c8-4311-844e-cc929dfd2557.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/8853/4dcad675-90c8-4311-844e-cc929dfd2557.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 [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2026-03-13&endDate=2026-03-15&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [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) In one month [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2026-04-03&endDate=2026-04-05&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2026-05-01&endDate=2026-05-03&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) ![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) ![Superior Suite, Ensuite (a The Suite)](https://images.trvl-media.com/lodging/10000000/9090000/9083300/9083253/bfc931de.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) ### 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 (428 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 $282 CA $320 total includes taxes & fees Apr 7 - Apr 8 [](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=2026-03-21&endDate=2026-03-22®ionId=8853&adults=2&lodging=BED_AND_BREAKFAST&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AA_SPRING_PROMO_8853) ![](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 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 "Was the best breakfast buffet, i had from any hotel!" [](https://expedia.ca/Corbin-Hotels-Holiday-Inn-Express-Williamsburg.h23240809.Hotel-Information) ![Super 8 by Wyndham Williamsburg](https://images.trvl-media.com/lodging/1000000/10000/7000/6940/a5cd488f_y.jpg) ### Super 8 by Wyndham Williamsburg 2/10 Terrible "Microwave didn't work, they didn't have one in the lobby or kitchen. Room was dirty. The place was smelly. Breakfast was coffee and a waffle or raisen bran. No juice or tea .I WILL NEVER STAY AT SUPER 8 AGAIN!!!! " [](https://expedia.ca/Corbin-Hotels-Super-8-By-Wyndham-Williamsburg.h6940.Hotel-Information) ![Days Inn by Wyndham Jellico - Tennessee State Line](https://images.trvl-media.com/lodging/1000000/10000/300/279/ad47702e_y.jpg) ### Days Inn by Wyndham Jellico - Tennessee State Line 6/10 Okay "It was a quick stop on our way to Florida. Close to interstate. " [](https://expedia.ca/Caryville-Hotels-Days-Inn-By-Wyndham-Jellico-Tennessee-State-Line.h279.Hotel-Information) ![The Olde Mill Inn Bed & Breakfast](https://images.trvl-media.com/lodging/10000000/9090000/9083300/9083253/5d5e1e35_y.jpg) ### The Olde Mill Inn Bed & Breakfast 10/10 Excellent "We enjoyed this cozy bed and breakfast. It's a great location - so beautiful! The staff was amazing - we had a meeting at LMU and were missing breakfast. So they packed us a breakfast and put it in the common area refrigerator for us to grab in the morning. It was also handy to fill our cups with ice water. " [](https://expedia.ca/Cumberland-Gap-Hotels-The-Olde-Mill-Inn-Bed-Breakfast.h9083253.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 "We stayed in one of the cottages..it was a nice weekend break..Staff was friendly & helpful at check in & check out..Also ate at the lodge (catfish & cheeseburger & salad bar..catfish was some of the best ive had & the salad bar was nice also.) Also had their continental breakfast was nice..eggs, sausage, biscuits, gravy, waffles cereal, oatmeal,bagels, bread, danishes & drinks..Restaurant staff where very friendly & helpful also" [](https://expedia.ca/Corbin-Hotels-Pine-Mountain-State-Resort-Park.h1109434.Hotel-Information) ![Sleep Inn & Suites Middlesboro](https://images.trvl-media.com/lodging/4000000/3930000/3929600/3929546/86beaca2_y.jpg) ### Sleep Inn & Suites Middlesboro 6/10 Okay "The staff is attentive and helpful. The room is large and clean. Now the bad. Tv and wifi are a joke!! The TVs are so old you can’t stream on them. I constantly have to go to my truck to get proper internet access. This is extremely annoying and corporate doesn’t care from what I hear. This makes it impossible to consistently do work here.. Get into the 21st century please! I will not stay here again and suggest to anyone traveling for business do the same. If corporate doesn’t care about it’s customers then I will move on to someplace that does!" [](https://expedia.ca/Middlesboro-Hotels-Sleep-Inn-Suites.h3929546.Hotel-Information) ![Quality Inn Harlan](https://images.trvl-media.com/lodging/1000000/20000/17000/16941/b003bff0_y.jpg) ### Quality Inn Harlan 4/10 Poor "Room was dirty " [](https://expedia.ca/Harlan-Hotels-Quality-Inn.h16941.Hotel-Information) ![Holiday Inn Express Middlesboro by IHG](https://images.trvl-media.com/lodging/1000000/70000/60900/60850/fba51913_y.jpg) ### Holiday Inn Express Middlesboro by IHG 10/10 Excellent "Very nice and clean. " [](https://expedia.ca/Middlesboro-Hotels-Holiday-Inn-Express-Middlesboro.h60850.Hotel-Information) ![Cumberland Gap Inn](https://images.trvl-media.com/lodging/15000000/14800000/14794500/14794465/58cb8c99_y.jpg) ### Cumberland Gap Inn 10/10 Excellent "The lady that checked us in was very nice and welcoming. The room was clean and comfortable. It had a nice patio overlooking a creek; what a nice suprise. The bed was comfortable. The shower had good water pressure and plenty of hot water. I would stay here again. " [](https://expedia.ca/Cumberland-Gap-Hotels-Cumberland-Gap-Inn.h14794465.Hotel-Information) ## Find out more about Middlesboro ## Middlesboro B&B information | Number of reviews | 428 | | ----------------- | ------- | | Accommodation | 1 B&B | | Lowest Price | CA $320 | | Highest Price | CA $320 | ## 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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