Middlesboro Holidays

Middlesboro Country Club

Established in 1889, Middlesboro Country Club is America's oldest continuously played nine-hole golf course. Challenge yourself on undulating greens while surrounded by breathtaking Appalachian Mountain vistas.

See properties

Bell County Historical Society Museum

Rating: 8.2/10 (13 reviews)

Housed in the historic 1915 Dr. J.D. Cawood House, the Bell County Museum preserves Kentucky's regional heritage. Explore artefacts and photographs telling local cultural stories within this National Register landmark.

See properties

Middlesboro Mall

Rating: 7.6/10 (62 reviews)

This regional shopping centre serves as a retail hub for Middlesboro with a mix of national and local stores. Browse fashion, home goods, and dining options in a straightforward, welcoming indoor environment.

See properties

Frequently Asked Questions

Why should I book my Middlesboro holiday with Expedia?

Expedia has you covered for all aspects of your upcoming Middlesboro trip. You'll always get the best prices, but when you bundle your flights, hotel and/or hire car into a holiday package, you'll get even bigger savings. Want to truly make the most of your adventure? Add some exciting tours and activities to your customised package. Expedia offers flexible cancellation policies on almost all bookings, so there's no need to worry if your travel plans change. Head over to our Customer Service Portal link to learn more.

When is the best time of year to holiday in Middlesboro?

Middlesboro gets busy in April, July and September. If you're not into big crowds and prefer a slower pace, lock in your escape for December, January and February. With daytime average temperatures of 1ºC, January is the coolest period in Middlesboro. The warmest month is July, when you can experience average temperatures of 24ºC throughout the day. Whatever the weather conditions, you'll find plenty of things to keep you entertained here.

What is the top hotel for my holiday in Middlesboro?

Offering many of the creature comforts of home, Sleep Inn & Suites will make the ideal base for your Middlesboro trip.

How do I get a cheap holiday to Middlesboro?

One of the simplest ways to save money (and time) is to combine your bookings with Expedia. Flights, hotels, activities and hire cars — we've got them all covered. Select a combination that suits you and watch your savings pile up. We know holidays are never a one-size-fits-all. That's why Expedia offers over 400 airlines and 321,000 hotel options worldwide, so you can customise your Middlesboro holiday your way. Learn more about how you can save money on your next holiday when you combine your hotel and flight bookings with Expedia.

What is the best area to stay in when on holiday in Middlesboro?

Middlesboro has many popular places to explore, like Cumberland Gap National Historical Park. Stay someplace nearby and make sightseeing a breeze.

Do I need a visa for my Middlesboro holiday?

Official government websites are the best source of information on visa requirements, application procedures and any supporting documentation. Your nationality and reason for travelling, whether it be for tourism or business, will determine if you need a visa for Middlesboro. Also double-check that your passport is up to date and has a minimum of six months validity remaining beyond your date of return. Do all your travel planning well ahead of time to avoid any last-minute surprises.

What should I wear on my Middlesboro holiday?

Do a little research into the sorts of things people in Middlesboro wear, and maybe even look up fashion pages on social media for inspiration. You'll want to create a versatile wardrobe full of pieces that work for your destination and showcase your personal style. Take a look at the local weather forecast so you can pack appropriately. The warmest month in Middlesboro is July, with average daily temperatures of 24ºC. If you're holidaying in the coolest month of January, the mercury averages 1ºC during the day.

What does an Expedia Middlesboro holiday include?

It depends on what sort of getaway you're planning. Middlesboro travel deals can include hotels, car hires and flights. You can mix and match to create the package that fits your needs. You can also add on activities and experiences after you've booked to land even bigger discounts. Explore a large range of property types and choose one that fits your group size. The most popular rentals here are hotels and private holiday homes. With Expedia, it's a breeze to tailor-make your Middlesboro escape however you want.

Does Expedia offer Book Now, Pay Later Middlesboro holidays?

Expedia has partnered with online lender Klarna to make booking your next trip a little easier on the wallet. Paying in instalments means you can spread the costs of your next dream escape, leaving you with more cash to play with while you're away. Klarna has several payment plans to choose from, so you're sure to find something that fits your budget. Browse these flexible payment options:

• Pay monthly holidays: If paying small amounts each month is something that would work for you, Klarna can help. Paying in convenient monthly instalments will make your getaway dreams come true.
• No-deposit holidays: Clicking the "book now" button is much easier with this option. With no deposit required for your getaway, you can Book Now, Pay Later and get on your way.

Can I choose my airline with a Middlesboro Expedia holiday?

You can. We have more than 400 airline partners worldwide, so choose the carrier that suits your budget needs.