Title: Book the Best Middlesboro Ski Hotels in 2025 from CA $322 | 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 Ski Hotels in Middlesboro, KY from CA $322 - ![](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 Ski Hotels Tonight [Nov 3 - Nov 4](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-11-03&endDate=2025-11-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 4 - Nov 5](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-11-04&endDate=2025-11-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Middlesboro Ski Hotels ![Exterior](https://images.trvl-media.com/lodging/34000000/33940000/33938700/33938643/d79c9131.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) ![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) ### 1928 Home in the heart of Cumberland Gap Cumberland Gap 9.8/10 Exceptional (93) "In town but no near neighbors; comfy and fun for close friends/relatives. (1 bath) Some antiques and restaurants close but quiet and clean" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul D. CA $252 CA $322 total includes taxes & fees Nov 4 - Nov 5 [](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=2025-11-17&endDate=2025-11-18®ionId=8853&adults=2&location_highlights_explore=ski&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 "Great breakfast. Room was spacious, clean and the dove products in the bathroom were nice. Great stay. " [](https://expedia.ca/Middlesboro-Hotels-Holiday-Inn-Express-Middlesboro.h60850.Hotel-Information) ## Frequently asked questions ### How much does a ski hotel in Middlesboro cost? > Prices for ski hotels in Middlesboro can vary, but you can find a great deal from CA $322 on Expedia. All sorts of factors affect price, such as the hotel's proximity to the slopes and the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates. ### Which area of Middlesboro is best to stay in for skiing? > When visiting Middlesboro for skiing, the best area to stay is in the city centre, particularly around Cumberland Avenue. > > > > This area is the main commercial and activity hub of Middlesboro. Cumberland Avenue, the primary thoroughfare, is lined with various local shops, eateries, and hotels, making it convenient for visitors. It's also well-connected to the main routes that lead out of the city towards the skiing destinations. > > > > For couples looking for a comfortable stay with easy access to dining and local amenities after a day on the slopes, the hotels along Cumberland Avenue are a practical choice. They offer a central location with a good selection of restaurants nearby for evening meals, and you're just a short drive from the skiing locations. > > > > For solo travellers, staying in the city centre offers a convenient base. ### Is it cheaper to book flights and a ski hotel in Middlesboro as a package? > Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates, and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect travel package. ### What dining options are typically available in Middlesboro ski accommodations? > Dining options in Middlesboro ski accommodations typically include a mix of on-site restaurants, casual eateries, and often self-catering facilities. > > > > Most accommodations, particularly larger hotels or lodges, provide at least one on-site restaurant offering breakfast, lunch, and dinner. These can range from fine dining experiences with a focus on local ingredients to more relaxed, family-friendly eateries. You'll often find options for American cuisine, sometimes with a Southern twist given the location. > > > > For guests preferring more flexibility, many accommodations also feature rooms or suites with kitchenettes or full kitchens. This allows you to prepare your own meals, which can be a convenient and cost-effective option, especially for longer stays or for families with specific dietary needs. Nearby grocery stores are usually accessible for stocking up on supplies. > > > > Additionally, some resorts might offer grab-and-go options like delis or cafes for quick snacks, coffee, and light meals. ### What activities should we do in Middlesboro besides skiing? > While skiing is a popular draw, Middlesboro and the surrounding area offer a variety of activities beyond the slopes. > > > > For those interested in history and the unique geological features of the region, exploring the Cumberland Gap National Historical Park is a must. This park, straddling Kentucky, Tennessee, and Virginia, is home to the famous Cumberland Gap, a natural pass through the Appalachian Mountains that was crucial for westward expansion. You can drive through the Gap, visit the Hensley Settlement – a preserved mountain community – or take a ranger-led tour to learn about the area's rich past. There are also numerous trails for all levels of hikers, offering scenic views of the surrounding mountains. > > > > Nature enthusiasts will also enjoy a visit to Pine Mountain State Resort Park, Kentucky's first state park. It's an excellent spot for couples or families looking for a relaxing day outdoors. The park features well-maintained hiking trails, including one leading to the scenic Chained Rock, a large boulder seemingly suspended by a giant chain. You can also enjoy a round of golf on its 18-hole course or simply take in the natural beauty from one of its many overlooks. > > > > If you're looking for something a bit more adventurous, consider exploring some of the local caves. The region is known for its karst topography, meaning there are several fascinating cave systems to discover. Guided tours are often available, providing an insight into the geological formations and history of these underground wonders. ### How can I save on a ski hotel in Middlesboro with Expedia? > Members always get our best prices. Find our best Middlesboro ski hotel deals by joining Expedia's free travel rewards program—[One Key™](https://www.expedia.ca/welcome-one-key). As a member, you can unlock instant savings and member perks when you're logged in. Another tip is to book your ski hotel in advance as availability and prices are usually better. If you are feeling spontaneous, there are last-minute offers to explore too. ### Can I cancel my ski hotel reservation on Expedia? > If your plans change, it's easy to cancel your hotel with free cancellation on Expedia. Just use the "Fully refundable property" filter during your search to find the right ski hotel in Middlesboro. 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