Title: Middlesboro Cottages from CA $295 | 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 # Search Middlesboro Cottage Rentals from CA $295 - ![](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 [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-11-28&endDate=2025-11-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Middlesboro Cottages ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121200000/121199100/121199061/5f60b3d0.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/ebf9cd54.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/cbbad019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121200000/121199100/121199061/7175025c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful & Private! Pet-friendly Williamsburg Home Williamsburg CA $151 CA $395 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Williamsburg-Hotels-Peaceful-Private-Pet-Friendly-Williamsburg-Home.h121199061.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) ![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) ![Dining](https://images.trvl-media.com/lodging/84000000/83790000/83783900/83783898/9e266762.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 (42) "Just as advertised. Very quiet and enjoyable stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $139 CA $295 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Cumberland-Gap-Hotels-Cozy-Cumberland-Gap-Cottage.h83783898.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/104000000/103940000/103938700/103938609/205d3a23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/104000000/103940000/103938700/103938609/89fe5d47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/104000000/103940000/103938700/103938609/19af1c21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103940000/103938700/103938609/e1250de4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater! Pineville 9.0/10 Wonderful (2) "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 $250 CA $402 total includes taxes & fees Dec 9 - Dec 10 [](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=2025-12-01&endDate=2025-12-02®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=2026-02-15&d1=2026-02-15&endDate=2026-02-18&d2=2026-02-18&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=2026-02-15&d1=2026-02-15&endDate=2026-02-18&d2=2026-02-18&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=2026-02-15&d1=2026-02-15&endDate=2026-02-18&d2=2026-02-18&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=2026-02-15&d1=2026-02-15&endDate=2026-02-18&d2=2026-02-18&lodging=APARTMENT) 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=2026-02-15&d1=2026-02-15&endDate=2026-02-18&d2=2026-02-18&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=2026-02-15&d1=2026-02-15&endDate=2026-02-18&d2=2026-02-18&lodging=VILLA) 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=2026-02-15&d1=2026-02-15&endDate=2026-02-18&d2=2026-02-18&lodging=HOUSE_BOAT) ![](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 ![Days Inn by Wyndham Jellico - Tennessee State Line](//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](//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 10/10 Excellent "The breakfast was very fresh with good flavor." [](https://expedia.ca/Middlesboro-Hotels-Sleep-Inn-Suites.h3929546.Hotel-Information) ![Quality Inn](//images.trvl-media.com/lodging/1000000/20000/17000/16941/b003bff0_y.jpg) ### Quality Inn 10/10 Excellent "The staff was really friendly and the beds were very comfortable. " [](https://expedia.ca/Harlan-Hotels-Quality-Inn.h16941.Hotel-Information) ### 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) ![Holiday Inn Express Williamsburg by IHG](//images.trvl-media.com/lodging/24000000/23250000/23240900/23240809/7b78ad82_y.jpg) ### Holiday Inn Express Williamsburg by IHG 10/10 Excellent "Nice comfortable and clean." [](https://expedia.ca/Corbin-Hotels-Holiday-Inn-Express-Williamsburg.h23240809.Hotel-Information) ### The Olde Mill Inn Bed & Breakfast 10/10 Excellent "Nice place in historic Cumberland Gap, walkable to hiking trail and pave local trail. The room is spacious, very clean, and comfortable bed. Homemade breakfast was delicious." [](https://expedia.ca/Cumberland-Gap-Hotels-The-Olde-Mill-Inn-Bed-Breakfast.h9083253.Hotel-Information) ### Beautiful Norris Lake Front A-Frame with Private Dock in Speedwell, Tn . 10/10 Excellent "Clean, nicely furnished, beautiful location. Very pleasant stay. " [](https://expedia.ca/Speedwell-Hotels-Beautiful-Norris-Lake-Front-A-Frame-With-Private-Dock-And-Jet-Skit-Lift.h66936119.Hotel-Information) ### Imperial Inn by OYO Tazewell 10/10 Excellent "Clean new room. Friendly family owned place. Only thing lacking was no coffee maker. " [](https://expedia.ca/Tazewell-Hotels-Imperial-Inn.h113960224.Hotel-Information) ## Find out more about Middlesboro ## Middlesboro Cottages information | Number of reviews | 39 | | --- | --- | | Accommodation | 11 Cottages | | Lowest Price | CA $295 | | Highest Price | CA $402 | ## Frequently asked questions ### Why book your cottage in Middlesboro with Expedia? > We think that a vacation should be hassle-free, so if you're searching for cottages in Middlesboro at a great price, Expedia has your back. Keep the budget under control and stay in an inexpensive option surrounded by nature, or splurge on a 5-star cottage to spoil your favorite people. ### How can I find cheap cottages in Middlesboro? > The simplest way to get cheap cottages in Middlesboro is with Expedia's convenient filter tool. Narrow down your search by star rating, amenities and budget to secure unbeatable deals in a couple of clicks. ### What is there to do in Middlesboro near my cottage? > The most useful travel accessory is a well-planned to-do list. 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