Title: Middlesboro Cottages from CA $292 | 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 ![](https://images.trvl-media.com/place/8853/b202c2ca-a802-49c4-b0c7-db992700a740.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 In two weeks [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Middlesboro cottages ![Exterior](https://images.trvl-media.com/lodging/84000000/83790000/83783900/83783898/14621cf9.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) ![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) ![Dining](https://images.trvl-media.com/lodging/84000000/83790000/83783900/83783898/abdc1ca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Cumberland Gap [](https://www.expedia.ca/Cumberland-Gap-Hotels-Cozy-Cumberland-Gap-Cottage.h83783898.Hotel-Information) 9.2/10 Wonderful (42 reviews) "Great location. Easy walk to town and close to hiking areas. Highly recommend. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda O. CA $137 CA $292 total includes taxes & fees Jan 23 - Jan 24 [](https://www.expedia.ca/Cumberland-Gap-Hotels-Cozy-Cumberland-Gap-Cottage.h83783898.Hotel-Information) ![House (2 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/122000000/121200000/121199100/121199061/7b8fb7b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121200000/121199100/121199061/3ebc65a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121200000/121199100/121199061/d2d84abe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121200000/121199100/121199061/e44cf9e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Williamsburg [](https://www.expedia.ca/Williamsburg-Hotels-Peaceful-Private-Pet-Friendly-Williamsburg-Home.h121199061.Hotel-Information) CA $136 CA $426 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Williamsburg-Hotels-Peaceful-Private-Pet-Friendly-Williamsburg-Home.h121199061.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/84000000/83700000/83695800/83695713/c3ca0191.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83700000/83695800/83695713/8c08cce2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/84000000/83700000/83695800/83695713/dbd9d55f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/84000000/83700000/83695800/83695713/23f18363.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Speedwell [](https://www.expedia.ca/Speedwell-Hotels-The-Cottage-At-Silver-Creek-Farms.h83695713.Hotel-Information) 9.4/10 Exceptional (22 reviews) "The hosts was great to communicate with. Everything was so smooth. There is a Dollar General down the road if you need quick groceries. House was clean and in good shape. We loved the creek behind the house. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Autumn CA $151 CA $364 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Speedwell-Hotels-The-Cottage-At-Silver-Creek-Farms.h83695713.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/125000000/124490000/124488800/124488708/65855ac8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/125000000/124490000/124488800/124488708/49eb2f4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/125000000/124490000/124488800/124488708/w3024h3872x0y0-05648119.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/125000000/124490000/124488800/124488708/b8a627bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Hinkle [](https://www.expedia.ca/Robertson-Ridge-Hideaway-Cottage.h124488708.Hotel-Information) CA $156 CA $203 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Robertson-Ridge-Hideaway-Cottage.h124488708.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/104000000/103940000/103938700/103938609/569aa3f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103940000/103938700/103938609/d880e84f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103940000/103938700/103938609/944b87f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/104000000/103940000/103938700/103938609/08ff3b78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Pineville [](https://www.expedia.ca/Pineville-Hotels-The-House-On-Park-Avenue-Minutes-To-Music-Venues-Laurel-Cove-And-Bell-Theater.h103938609.Hotel-Information) 9.0/10 Wonderful (2 reviews) "The home was just perfect for what we needed. Looking forward to seeing how it comes out when all construction is finished! Host was very responsive. Will stay again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kami L. CA $217 CA $448 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Pineville-Hotels-The-House-On-Park-Avenue-Minutes-To-Music-Venues-Laurel-Cove-And-Bell-Theater.h103938609.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=2026-01-27&endDate=2026-01-28®ionId=8853&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.ca/Hotel-Search?destination=Middlesboro%2C+Kentucky%2C+United+States+of+America®ionId=8853&latLong=36.608416%2C-83.716582&adults=2&startDate=2026-04-13&d1=2026-04-13&endDate=2026-04-16&d2=2026-04-16&lodging=CABIN) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Middlesboro%2C+Kentucky%2C+United+States+of+America®ionId=8853&latLong=36.608416%2C-83.716582&adults=2&startDate=2026-04-13&d1=2026-04-13&endDate=2026-04-16&d2=2026-04-16&lodging=VACATION_HOME) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Middlesboro%2C+Kentucky%2C+United+States+of+America®ionId=8853&latLong=36.608416%2C-83.716582&adults=2&startDate=2026-04-13&d1=2026-04-13&endDate=2026-04-16&d2=2026-04-16&lodging=COTTAGE) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Middlesboro%2C+Kentucky%2C+United+States+of+America®ionId=8853&latLong=36.608416%2C-83.716582&adults=2&startDate=2026-04-13&d1=2026-04-13&endDate=2026-04-16&d2=2026-04-16&lodging=APARTMENT) Houseboats [](https://www.expedia.ca/Hotel-Search?destination=Middlesboro%2C+Kentucky%2C+United+States+of+America®ionId=8853&latLong=36.608416%2C-83.716582&adults=2&startDate=2026-04-13&d1=2026-04-13&endDate=2026-04-16&d2=2026-04-16&lodging=HOUSE_BOAT) Condos [](https://www.expedia.ca/Hotel-Search?destination=Middlesboro%2C+Kentucky%2C+United+States+of+America®ionId=8853&latLong=36.608416%2C-83.716582&adults=2&startDate=2026-04-13&d1=2026-04-13&endDate=2026-04-16&d2=2026-04-16&lodging=CONDO) Villas [](https://www.expedia.ca/Hotel-Search?destination=Middlesboro%2C+Kentucky%2C+United+States+of+America®ionId=8853&latLong=36.608416%2C-83.716582&adults=2&startDate=2026-04-13&d1=2026-04-13&endDate=2026-04-16&d2=2026-04-16&lodging=VILLA) ![](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-Cottages.d8853-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FMiddlesboro-Cottages.d8853-aaCottages.Travel-Guide-Accommodation) ## Top Middlesboro Hotel Reviews ![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) ![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 "Amazing guest they made it feel like home! Wonderful staff, amazing food . Great customer service ! I Highly recommend staying here. Most likely every-time we come down to visit family we will stay there. " [](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/a3c8a3ba_y.jpg) ### Cumberland Gap Inn 10/10 Excellent "The beds were comfy, it was quiet and clean. We will book here again in the future!" [](https://expedia.ca/Cumberland-Gap-Hotels-Cumberland-Gap-Inn.h14794465.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) ![Econo Lodge Middlesboro](https://images.trvl-media.com/lodging/1000000/20000/15200/15146/853995b8_y.jpg) ### Econo Lodge Middlesboro 10/10 Excellent "Everything fine " [](https://expedia.ca/Middlesboro-Hotels-Econo-Lodge.h15146.Hotel-Information) ## Find out more about Middlesboro ## Middlesboro Cottages information | Number of reviews | 63 | | ----------------- | ----------- | | Accommodation | 12 Cottages | | Lowest Price | CA $292 | | Highest Price | CA $448 | ## Frequently asked questions ### Why book your cottage in Middlesboro with Expedia? ### How can I find cheap cottages in Middlesboro? ### What is there to do in Middlesboro near my cottage? ## 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) - 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