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 $130 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 3 - Oct 4](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-10-03&endDate=2025-10-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 4 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-10-04&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-10-10&endDate=2025-10-12&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) ![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) ![Standard Room, Balcony, Mountain View | Aerial view](https://images.trvl-media.com/lodging/2000000/1110000/1109500/1109434/d38a5bd3.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) ### Pine Mountain State Resort Park Pineville 9.0/10 Wonderful (622) "Great place to stay on a weekend trip" CA $118 CA $130 total includes taxes & fees Oct 8 - Oct 9 [](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) ![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) ![Miscellaneous](https://images.trvl-media.com/lodging/10000000/9090000/9083300/9083253/b8a5ded6.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 $172 CA $195 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Cumberland-Gap-Hotels-The-Olde-Mill-Inn-Bed-Breakfast.h9083253.Hotel-Information) ![Honeymoon Suite, 1 King Bed](https://images.trvl-media.com/lodging/15000000/14800000/14794500/14794465/a3c8a3ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/15000000/14800000/14794500/14794465/e27de054.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sundeck](https://images.trvl-media.com/lodging/15000000/14800000/14794500/14794465/08c2b2f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Honeymoon Suite, 1 King Bed | Room amenity](https://images.trvl-media.com/lodging/15000000/14800000/14794500/14794465/a793dced.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cumberland Gap Inn Cumberland Gap 8.0/10 Very good (580) "Great stay" CA $137 CA $155 total includes taxes & fees Oct 4 - Oct 5 [](https://www.expedia.ca/Cumberland-Gap-Hotels-Cumberland-Gap-Inn.h14794465.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) ![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) ![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) ![TV, books, offices](https://images.trvl-media.com/lodging/84000000/83790000/83783900/83783898/d356b353.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 $138 CA $294 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Cumberland-Gap-Hotels-Cozy-Cumberland-Gap-Cottage.h83783898.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=2025-10-17&endDate=2025-10-18®ionId=8853&adults=2&nearby_group=recreation&sort=RECOMMENDED&openPlayBack=true) ## Top Middlesboro Hotel Reviews ![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) ![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 "Love it " [](https://expedia.ca/Corbin-Hotels-Pine-Mountain-State-Resort-Park.h1109434.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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