Title: Book the Best Middlesboro MOUNTAIN Hotels & Resorts 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) ![#Adventure #CumberlandGap #High #Trees #Highway](https://images.trvl-media.com/place/8853/b202c2ca-a802-49c4-b0c7-db992700a740.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Alexis Wyrick # Find Mountain Hotels in Middlesboro, KY from CA $101 - ![](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 Mountain Hotels Tonight [Nov 19 - Nov 20](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-11-19&endDate=2025-11-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 20 - Nov 21](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-11-20&endDate=2025-11-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-11-21&endDate=2025-11-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-11-28&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Middlesboro Mountain Hotels ![Front of property](https://images.trvl-media.com/lodging/1000000/10000/300/279/b362fe26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/300/279/55a3ab12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Laundry room](https://images.trvl-media.com/lodging/1000000/10000/300/279/08173c4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/300/279/6adc7a76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn by Wyndham Jellico - Tennessee State Line Jellico 7.2/10 Good (1004) "Very clean and quiet I loved and enjoyed my 3 nights and 4 day stay!!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Antoninette CA $88 CA $101 total includes taxes & fees Nov 27 - Nov 28 [](https://www.expedia.ca/Caryville-Hotels-Days-Inn-By-Wyndham-Jellico-Tennessee-State-Line.h279.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/24000000/23250000/23240900/23240809/7b78ad82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/24000000/23250000/23240900/23240809/7f7a598a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/24000000/23250000/23240900/23240809/4cc09473.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/24000000/23250000/23240900/23240809/cf8d091b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Williamsburg by IHG Williamsburg 9.0/10 Wonderful (1002) "We really enjoyed our stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea Strode CA $168 CA $190 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Corbin-Hotels-Holiday-Inn-Express-Williamsburg.h23240809.Hotel-Information) ![Standard Room](https://images.trvl-media.com/lodging/1000000/70000/60900/60850/3963de73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/70000/60900/60850/d8f164b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/70000/60900/60850/2eaf3737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/70000/60900/60850/fba51913.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Middlesboro by IHG Middlesboro 9.6/10 Exceptional (690) "Clean hotel, good breakfast options." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Harold CA $165 CA $182 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Middlesboro-Hotels-Holiday-Inn-Express-Middlesboro.h60850.Hotel-Information) ![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) ![Interior entrance](https://images.trvl-media.com/lodging/2000000/1110000/1109500/1109434/4ec8d24c.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 (657) "Staff were amazing! Very unique experience in the cottage and the fireplace was really special highly recommended!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrew CA $137 CA $151 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Corbin-Hotels-Pine-Mountain-State-Resort-Park.h1109434.Hotel-Information) ![Standard Room, 2 Double Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/20000/15200/15146/853995b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 10:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/15200/15146/c38450c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Snack bar](https://images.trvl-media.com/lodging/1000000/20000/15200/15146/5b2610cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/15200/15146/c30cd65d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Econo Lodge Middlesboro Middlesboro 7.2/10 Good (442) "Clean place with friendly staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $102 CA $113 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Middlesboro-Hotels-Econo-Lodge.h15146.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) ![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 | Living area](https://images.trvl-media.com/lodging/15000000/14800000/14794500/14794465/e0dcd922.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 (583) "The views around the area are beautiful and the town is peaceful and quiet " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $137 CA $155 total includes taxes & fees Nov 21 - Nov 22 [](https://www.expedia.ca/Cumberland-Gap-Hotels-Cumberland-Gap-Inn.h14794465.Hotel-Information) ![Comfort House | Private kitchen](https://images.trvl-media.com/lodging/105000000/104290000/104287200/104287199/fb66dac6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort House | Bathroom](https://images.trvl-media.com/lodging/105000000/104290000/104287200/104287199/43f54380.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort House](https://images.trvl-media.com/lodging/105000000/104290000/104287200/104287199/edafc421.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort House | Living area](https://images.trvl-media.com/lodging/105000000/104290000/104287200/104287199/ceaca54c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The House on Park Avenue Pineville CA $394 CA $545 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Pineville-Hotels-The-House-On-Park-Avenue.h104287199.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=2025-12-03&endDate=2025-12-04®ionId=8853&adults=2&location_highlights_explore=mountain&sort=RECOMMENDED&openPlayBack=true) ## Top Middlesboro Hotel Reviews ![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 "The staff was friendly, the room was clean and well stocked, the TV and internet worked great. I would definitely recommend this Days Inn." [](https://expedia.ca/Caryville-Hotels-Days-Inn-By-Wyndham-Jellico-Tennessee-State-Line.h279.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 have been to a lot of State Parks over the years and this one might be the best. Great views. The staff and service were amazing, and our cabin was nice and clean. We ate breakfast and dinner at the lodge several times and it was always fantastic. The alcohol menu is really nice, plenty of variety and reasonably priced. They offer more amenities than other parks like borrowing a fishing pole and tackle box for the lake. You can also borrow board games from the game room to take to your room/cabin. The game room also has a ping pong table, a table-size Connect4 game and other cool things. Pet friendly. The hiking trails were clear and labeled well with plenty of signs. We will be visiting again." [](https://expedia.ca/Corbin-Hotels-Pine-Mountain-State-Resort-Park.h1109434.Hotel-Information) ![Sleep Inn & Suites Middlesboro](https://images.trvl-media.com/lodging/4000000/3930000/3929600/3929546/1cf62fd0_y.jpg) ### Sleep Inn & Suites Middlesboro 10/10 Excellent "The breakfast was very fresh with good flavor." [](https://expedia.ca/Middlesboro-Hotels-Sleep-Inn-Suites.h3929546.Hotel-Information) ![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 "Very comfortable and clean." [](https://expedia.ca/Middlesboro-Hotels-Holiday-Inn-Express-Middlesboro.h60850.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - [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) - [Motels in Barbourville](https://www.expedia.ca/Barbourville-Motels.d6267-aaMotels.Travel-Guide-Accommodation) - [Bimble Hotels](https://www.expedia.ca/Bimble-Hotels.d3000347273.Travel-Guide-Hotels) - [Hotels near Black Mountain](https://www.expedia.ca/Black-Mountain-Hotels.0-l6091535-0.Travel-Guide-Filter-Hotels) - [Hotels near Boone's Ridge Wildlife Park](https://www.expedia.ca/Boones-Ridge-Wildlife-Park-Hotels.0-l814992773973426176-0.Travel-Guide-Filter-Hotels) - [Apartments in Calvin](https://www.expedia.ca/Calvin-Apartments.d3000347285-aaApartments.Travel-Guide-Accommodation) - 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[Flights to Barbourville](https://www.expedia.ca/Cheap-Flights-To-Barbourville.d6267.Travel-Guide-Flights) - [Flights to Corbin](https://www.expedia.ca/Cheap-Flights-To-Corbin.d6059437.Travel-Guide-Flights) - [Flights to Harlan](https://www.expedia.ca/Cheap-Flights-To-Harlan.d8279.Travel-Guide-Flights) - [Flights to Williamsburg](https://www.expedia.ca/Cheap-Flights-To-Williamsburg.d7856.Travel-Guide-Flights) - [Flights from Calvin](https://www.expedia.ca/lp/flights/3000347285/flights-from-calvin) - [Flights from Rockholds](https://www.expedia.ca/lp/flights/3000347450/flights-from-rockholds) - [Flights from Harlan County](https://www.expedia.ca/lp/flights/553248635976433995/flights-from-harlan-county) - [Flights from Barbourville](https://www.expedia.ca/lp/flights/6267/flights-from-barbourville) - [Bimble Vacations](https://www.expedia.ca/Bimble.d3000347273.Destination-Travel-Guides) - [Corbin Vacations](https://www.expedia.ca/Corbin.d6059437.Destination-Travel-Guides) - [Visit Harlan](https://www.expedia.ca/Harlan.dx8279) - [Visit North Corbin](https://www.expedia.ca/North-Corbin.dx553248634999089098) - [Rapid River Lodge & Water Park](https://www.expedia.ca/Rapid-River-Lodge-Water-Park-Kentucky.d553248621532651998.Vacation-Attraction) - [Car rental Corbin](https://www.expedia.ca/Car-Rentals-In-Corbin.d6059437.Car-Rental-Guide) - [Car rental Harlan](https://www.expedia.ca/Car-Rentals-In-Harlan.d8279.Car-Rental-Guide) - [Car rental Williamsburg](https://www.expedia.ca/Car-Rentals-In-Williamsburg.d7856.Car-Rental-Guide) - [Corbin Vacation Rentals](https://www.expedia.ca/Corbin-Vacation-Rentals.d6059437.Travel-Guide-VacationRentals) - [Gray Vacation Rentals](https://www.expedia.ca/Gray-Vacation-Rentals.d889086718113042432.Travel-Guide-VacationRentals)