32+ Vacation Rentals in Middlesboro |
  1. USA
  2. Kentucky
  3. Middlesboro

Middlesboro Vacation Rentals, Hotels, & Places to Stay

About Middlesboro Vacation Rentals

There are more than 32 places to stay that are available in Middlesboro. These choices include hotels as well as other short-term private accommodations (including vacation rentals, cabins, condos, RVs, and more), have a wide selection of amenities at great prices, providing you with all the comforts of home or a touch of luxury. We like to help you find more room with Varoom when booking your property in Middlesboro.

Varoom features many last-minute deals on hotels, resorts and places to stay including many that are nearby. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With Varoom's places in Middlesboro, you have the flexibility of comparing different options from multiple suppliers with a single click. Group deals, private pools, hot tubs, allows pets, or even those with huge master suite bedrooms with open-air showers? You can find vacation rentals and resorts as well as Airbnb-style properties in Middlesboro. Places to stay near Middlesboro are 863.66 ft² on average, with prices averaging US $217 a night.

Varoom helps you discover places to stay and suggests things to do to create great travel memories in Middlesboro. Prices listed are often found to be at a 30-40% discount versus the rack rates. Just search for your destination and secure your perfect place to stay today.

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Top Rental Accommodation Types in Middlesboro

Type Count
Vacation Homes 15
Holiday Apartments 3
Cottages 1
Villas 1

Use these Quick Filters to Find a Vacation Rental in Middlesboro

★ Pro Tip: Varoom is a meta travel and activities site, and as such we combine results from many of the leading travel websites, helping you compare the best places to stay and things to do in each market. Use the filter option to narrow down your selection and let us help you find more room to stay, play, and discover. Create new memories in Middlesboro today.

Weather in Middlesboro, KY

View the weather forecast for Middlesboro before booking your Middlesboro Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Middlesboro, KY

Varoom offers a large selection of top attractions around Middlesboro . Research things to do on your vacation before you visit Middlesboro.


Cumberland Gap National Historical Park
Middlesboro Mall
Bell County Historical Society Museum
Middlesboro ARH Hospital
Cherokee Reservoir
Norris Lake
Pine Mountain State Resort Park
C.W. Gose Municipal Park
Lone Mountain Boat Dock
Straight Creek Boat Dock
Harlan Appalachian Regional Healthcare Hospital
Barbourville Water Park
Martins Fork Lake - Smith Recreation Area
Dr Thomas Walker State Park
The Harlan Center
Dr. Thomas Walker State Historic Site
Indian Mountain State Park
Memorial Park
Wasioto Winds Golf Course
Wilderness Road State Park

Other Places to Stay in Middlesboro, KY


Middlesboro ARH Hospital 31 Properties
Cumberland Gap National Historical Park 31 Properties
Middlesboro Mall 28 Properties
Bell County Historical Society Museum 28 Properties

Complexes around Middlesboro, KY


Holiday Inn Express Middlesboro Ihg Hotel 2 Properties

Frequently Asked Questions About Middlesboro?

What are the top vacation rentals in Middlesboro?

We have scoured the web to find you options in Middlesboro. If you plan on staying near or in the Middlesboro area, consider one of the following places to stay for a week or more. Weekly stays are a great way to unwind and unplug. These places to stay have all been rated as one of the the Top Places to Stay in Middlesboro:

How many Varoom vacation rentals are available in Middlesboro?

Varoom updates its properties nightly to bring you a great selection of places to stay. Currently, the total number of properties listed by Varoom in 2025 is over 32 in the Middlesboro area, and still growing every day. When we combine listings from multiple websites and travel providers, Varoom can provide you with a diverse amount of choice of the best places to stay in Middlesboro. 


People Also Ask

There are 32 Middlesboro, KY Vacation Rentals

Recently Booked Vacation Rentals in Middlesboro