Title: Book the Best Middlesboro Ski Hotels in 2026 from CA $315 | Expedia.ca

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![#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

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## Check availability on Middlesboro Ski Hotels

Tonight

[Jan 16 - Jan 17](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2026-01-16&endDate=2026-01-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Jan 17 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2026-01-17&endDate=2026-01-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2026-01-16&endDate=2026-01-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2026-01-23&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Middlesboro ski hotels

![Interior](https://images.trvl-media.com/lodging/122000000/121680000/121672900/121672802/5d1e81f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/122000000/121680000/121672900/121672802/747e600e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121680000/121672900/121672802/d2efa0c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121680000/121672900/121672802/4083eae8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Highlands Cabin Retreat at Norris Lake

[](https://www.expedia.ca/New-Tazewell-Hotels-The-Highlands-Cabin-Retreat-At-Norris-Lake.h121672802.Hotel-Information)

New Tazewell

10/10

Exceptional

(2 reviews)

"The cabin was clean, cozy, and overall amazing! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Fannie

CA $181

CA $315 total

includes taxes & fees

Jan 18 - Jan 19

[](https://www.expedia.ca/New-Tazewell-Hotels-The-Highlands-Cabin-Retreat-At-Norris-Lake.h121672802.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/123000000/122730000/122721800/122721728/f82afa15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122730000/122721800/122721728/5622756e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/123000000/122730000/122721800/122721728/90de5c90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/123000000/122730000/122721800/122721728/0e9f14a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Jackson MTN Retreat 3-bedroom entire HOME in Harrogate-Near LMU & Bowling alley

[](https://www.expedia.ca/Harrogate-Hotels-Jackson-MTN-Retreat-3-Bedroom-Entire-HOME-In-Harrogate-Near-LMU-Bowling-Alley.h122721728.Hotel-Information)

Harrogate

CA $276

CA $630 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Harrogate-Hotels-Jackson-MTN-Retreat-3-Bedroom-Entire-HOME-In-Harrogate-Near-LMU-Bowling-Alley.h122721728.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=2026-01-30&endDate=2026-01-31&regionId=8853&adults=2&location_highlights_explore=ski&sort=RECOMMENDED&openPlayBack=true)

## Top Middlesboro Hotel Reviews

![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

"Clean room"

[](https://expedia.ca/Middlesboro-Hotels-Holiday-Inn-Express-Middlesboro.h60850.Hotel-Information)

## Frequently asked questions

### How much does a ski hotel in Middlesboro cost?

### Which area of Middlesboro is best to stay in for skiing?

> 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?

### What dining options are typically available in Middlesboro ski accommodations?

> 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?

> 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?

### Can I cancel my ski hotel reservation on Expedia?

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