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Middlesboro vacation rentals

We found 21 vacation rentals — enter your dates for availability

your current months are April, 2024 and May, 2024.
April 2024
May 2024
Scroll through and select from vacation rentals in Middlesboro to find one that's perfect for your trip. Vacation homes offer the best amenities for your family, friends, or furry companion, like WiFi and parking. At the end of the day, you'll be sure to find a rental that has what everyone needs, including accessible or non-smoking choices.

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Take in the majestic beauty of Middlesboro

Enjoy the churches and other features of Middlesboro. Renowned for its mountain views, hiking and wildlife, this city welcomes all visitors. Whether you're planning a family vacation, friends trip or romantic retreat, Vrbo has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Sightseeing in and around Middlesboro

Are you looking for things to do while you're in town? Venture out of your cozy vacation rental and experience everything that Middlesboro has to offer. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Lone Mountain Boat Dock (17.2 mi / 27.6 km)
  • Barbourville Water Park (20.7 mi / 33.3 km)
  • Middlesboro Country Club (1 mi / 1.6 km)
  • Wasioto Winds Golf Course (8.9 mi / 14.3 km)

Exploring the natural features in Middlesboro

Whether you're looking for adventure or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Middlesboro. Here are some of the area’s most enchanting features, all within 30 miles (48.2 km) of the city center:

  • Cumberland Gap National Historical Park (2.4 mi / 3.9 km)
  • Pine Mountain State Resort Park (9.5 mi / 15.4 km)
  • C.W. Gose Municipal Park (13.4 mi / 21.5 km)
  • Norris Lake (24.3 mi / 39.1 km)
  • Wilderness Road State Park (10.8 mi / 17.4 km)
  • The Pinnacle (2.8 mi / 4.6 km)

Frequently asked questions

What is the most popular type of vacation rental accommodation in Middlesboro?

Houses are the most popular kind of vacation rental in Middlesboro, according to our data. Even if you have something a little different in mind, Vrbo has properties in loads of shapes and sizes. Look over our options to find your ideal match.

How much does it cost to rent a vacation rental in Middlesboro?

Several factors can affect what you'll pay for a vacation rental in Middlesboro, like the length of stay, type of property and season. However, all of our vacation homes have something in common — unbeatable value. Just add your travel dates to find your ideal match.

How much does it cost to rent a beach house in Middlesboro?

When you travel and the style and size of the property will help determine the cost of your beachside vacation rental. Click on your Middlesboro travel dates to view your options on Vrbo. Did someone just say "private pool"? Use the filters to select the amenities and features you want in your rental.

What are popular rental amenities in Middlesboro?

When it comes to rental amenities that guests are looking for in Middlesboro, a nearby river, an oven and a porch are the most popular. With Vrbo vacation rentals, there are options to fit your style and taste, whether you're traveling with friends, family or even pets.

What are the top attractions for families in Middlesboro?

There's no time to get bored during your Middlesboro trip with these family-friendly attractions:

  • Bell County Historical Society Museum
  • Middlesboro Mall

How old do you have to be to rent a vacation rental in Middlesboro?

The minimum age can differ across properties on Vrbo, so be sure to look at the rules of the vacation home in Middlesboro you're considering. But typically, it's 16, 18 or 21.

How long can I rent a vacation rental in Middlesboro for?

The amount of time you can rent a Middlesboro vacation rental for depends on the property. Simply put in your preferred travel dates to find options offering longer term stays. They come with the things you need to make your extended vacation more enjoyable and convenient, such as air conditioning and kitchens. Some properties may also offer weekly or monthly discounted prices, so you can stay even longer for less.

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