Middlesboro, Kentucky holiday accommodation: short-term house rentals & properties

Scroll through and select from holiday rentals in Middlesboro to find one that's perfect for your trip. Holiday homes provide the best amenities for you and your friends, family or even pets, such as cable TV and a washer and dryer. Whatever you're looking for, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Middlesboro

4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,

Sleeps 4 · 2 bedrooms · 1 bathroom

Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.

Sleeps 10 · 3 bedrooms · 2 bathrooms

Gorgeous 4-bedroom house in Middlesboro KY with WiFi, AC. Minutes from LMU

Sleeps 9 · 4 bedrooms · 2 bathrooms

A beautiful colonial house with breathtaking views of the Cumberland Gap Mnts!

Sleeps 14 · 5 bedrooms · 2 bathrooms

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

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 holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday 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

Do you want to find attractions to visit in the city? Venture out of your holiday home and experience everything that makes Middlesboro a fun place to get away to. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

Lone Mountain Boat Dock (17.2 mi / 27.6 km)
Middlesboro Country Club (1 mi / 1.6 km)
Wasioto Winds Golf Course (8.9 mi / 14.3 km)
Woodlake Lodge, Golf, and Country Club (16.8 mi / 27.1 km)
Barbourville Water Park (20.7 mi / 33.3 km)

Exploring the natural features in Middlesboro

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Middlesboro is a great place to get outside. Here are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

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)
The Pinnacle (2.8 mi / 4.6 km)
Kentucky Ridge State Forest (7.3 mi / 11.8 km)

Frequently asked questions

What is the most popular type of holiday home accommodation in Middlesboro?

Houses are the most popular kind of holiday home in Middlesboro, according to our data. Even if you have something a little different in mind, Stayz 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 holiday home in Middlesboro?

Several factors can affect what you’ll pay for a holiday home in Middlesboro, like the length of stay, type of property and season. However, all of our holiday 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 holiday home. Click on your Middlesboro travel dates to view your options on Stayz. Did someone just say “private pool”? Use the filters to select the amenities and features you want in your home.

What are popular home amenities in Middlesboro?

When it comes to home amenities that guests are looking for in Middlesboro, a nearby river, an oven and a porch are the most popular. With Stayz holiday homes, there are options to fit your style and taste, whether you’re travelling 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 holiday home in Middlesboro?

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

How long can I rent a holiday home in Middlesboro for?

The amount of time you can rent a Middlesboro holiday home 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 holiday 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.