Title: Book the Best ADVENTURE Hotels in Middlesboro in 2025 | 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 Hotels & Resorts for Couples in Middlesboro, KY from CA $116 ![](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 Hotels & Resorts for Couples Tonight [Oct 11 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-10-11&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 12 - Oct 13](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-10-12&endDate=2025-10-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Middlesboro Hotels & Resorts for Couples ![Outdoor wedding area](https://images.trvl-media.com/lodging/2000000/1110000/1109500/1109434/75b8d155.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1110000/1109500/1109434/4a64fadc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/2000000/1110000/1109500/1109434/4ec8d24c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/2000000/1110000/1109500/1109434/a5889142.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pine Mountain State Resort Park Pineville 9.0/10 Wonderful (630) "Great views, and wonderful trails, and pet-friendly." CA $106 CA $116 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Corbin-Hotels-Pine-Mountain-State-Resort-Park.h1109434.Hotel-Information) ![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/10000000/9090000/9083300/9083253/5d5e1e35.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/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) ![Exterior](https://images.trvl-media.com/lodging/84000000/83790000/83783900/83783898/1a7d1e20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/84000000/83790000/83783900/83783898/9e266762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/84000000/83790000/83783900/83783898/2703de40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83790000/83783900/83783898/fa489755.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Cumberland Gap Cottage Near LMU & Nat’l Park Cumberland Gap 9.2/10 Wonderful (39) "Just as advertised. Very quiet and enjoyable stay!" CA $139 CA $294 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Cumberland-Gap-Hotels-Cozy-Cumberland-Gap-Cottage.h83783898.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/34000000/33940000/33938700/33938643/d79c9131.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33940000/33938700/33938643/47ae19bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33940000/33938700/33938643/ab9d6df4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33940000/33938700/33938643/59a30a63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1928 Home in the heart of Cumberland Gap Cumberland Gap 9.8/10 Exceptional (91) "The host was easy to reach and the house was clean. Cumberland Gap has really nice trails to walk, and lots of antique stores. Shout out to the restaurant just down the street "1919" Great food We would definetly stay again." CA $280 CA $358 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Cumberland-Gap-Hotels-1928-Home-In-The-Heart-Of-Cumberland-Gap.h33938643.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=2025-10-25&endDate=2025-10-26®ionId=8853&adults=2&nearby_group=recreation&sort=RECOMMENDED&openPlayBack=true) ## 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 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) ## Frequently asked questions ### Why book your hotel for couples in Middlesboro with Expedia? > We believe that traveling with your sweetheart should be easy, so if you're on the lookout for a hotel for couples in Middlesboro at an affordable price, Expedia has you covered. Save those pennies and go for an inexpensive motel, or splurge and book a luxury hotel break to pamper the one you love the most. ### How can I find cheap hotels for couples in Middlesboro? > Expedia can help you track down cheap hotels for couples in Middlesboro. Make use of our filter tool to select star rating, budget and amenities to refine your search and reserve a wonderful place to get away with your sweetheart in just a few keystrokes. ### What is there to do in Middlesboro near my hotel for couples? > If you'd like to discover the best of Middlesboro, make your way to [Bell County Historical Society Museum](https://www.expedia.ca/Bell-County-Historical-Society-Museum-Middlesboro.d553248621561234927.Vacation-Attraction). 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