32+ Private Villas and Holiday Rentals in Middlesboro |
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  3. Middlesboro

Middlesboro Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Middlesboro

Discover more than 32 vacation rentals available in Middlesboro. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Middlesboro.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Middlesboro, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Middlesboro. On average, places to stay near Middlesboro offer 863.66 ft², with nightly prices averaging US $217.

With Casai, finding and comparing holiday rentals in Middlesboro is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Middlesboro

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

Use these Quick Filters to Find a Holiday Rental in Middlesboro

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Middlesboro.

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

Casai 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

Frequently Asked Questions About Middlesboro?

What are the top holiday rentals in Middlesboro?

With numerous options available in Middlesboro, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Middlesboro:

How many Casai.nz holiday rentals are available in Middlesboro?

As of 2025, Casai boasts over 32 properties listed in the Middlesboro area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Middlesboro.


People Also Ask

There are 32 Middlesboro, KY Holiday Rentals

Recently Booked Holiday Rentals in Middlesboro