Middlesboro Holiday Packages

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Book your Middlesboro holiday

Want to save a little cash with Wotif?

Our neat little package deals combine your hotels and flights to make life easy.

Your Middlesboro vacation is about to get way more fun.

You could gain savings of up to . And with more than 550 partner airlines and 665,000 worldwide properties, it's easy to craft your dream holiday.

With some of the most attractive deals online, you'll be soaring through the skies before you know it. So, grab your passport and get a wriggle on.

Middlesboro Accommodation

With only 3 accommodations in Middlesboro, securing a place to stay should be right at the top of your to-do list. Wotif has some awesome deals available right now, so what are you waiting for?

Really should have organised somewhere to stay by now? Left it to the last second? No probs — we've got your back. Try out The Olde Mill Inn Bed & Breakfast (603 Pennlyn Avenue) or the Sleep Inn & Suites (1260 N, 12th Street).

Car Hire in Middlesboro

Are you looking for the closest car rental outlet to the city? Enterprise (300 N 12th Street) is the best place to get your hands on some keys and an awesome ride.

Holidays to Middlesboro

Forgot that day at school when you were taught some basic info about Middlesboro? There's no need to throw a tanty over your lack of geography skills — we've got your back.

Middlesboro is just down the road from a couple of major cities that should help you get your bearings. Just 40 kilometres to the west is Williamsburg. The town isn't far from Corbin either. You only need to drive northwest for 50 kilometres before you hit it.

Travelling's about meeting heaps of new people and sharing fantastic experiences. With roughly 11 000 residents in this area of Eastern Kentucky, you're sure to encounter a few like-minded folk.

Top Middlesboro hotels

Holiday Inn Express Middlesboro by IHG

Holiday Inn Express Middlesboro by IHG

2.5 out of 5
1252 N 12th St Middlesboro KY
The price is AU$226 per night from 24 May to 25 May
AU$226
24 May - 25 May
includes taxes & fees
Holiday Inn Express Middlesboro by IHG: Business-friendly hotel with free breakfast and free WiFi. Located in a national park.
"Convenient location to Cumberland Gap National Park. Was a quiet hotel. Our room looked out to a section of the hillside. Restaurants within walking distance and Walmart was across the street."

Reviewed on 5 May 2026

Opens in a new windowHoliday Inn Express Middlesboro by IHG
Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro

2.5 out of 5
1260 N, 12th Street Middlesboro KY
Fully refundable
The price is AU$161 per night from 31 May to 1 June
AU$161
31 May - 1 June
includes taxes & fees
Sleep Inn & Suites Middlesboro: Pet-friendly hotel with free breakfast and free WiFi. Located in the city centre.
"It was good"

Reviewed on 18 May 2026

Opens in a new windowSleep Inn & Suites Middlesboro
Econo Lodge Middlesboro

Econo Lodge Middlesboro

2 out of 5
1623 Cumberland Avenue Middlesboro KY
Fully refundableReserve now, pay when you stay
The price is AU$120 per night from 2 June to 3 June
AU$120
2 June - 3 June
includes taxes & fees
Econo Lodge Middlesboro: Pet-friendly motel with free breakfast and free WiFi. Located in the mountains.
"Very nice people working there. Will stay again. Room we rented was nice and clean"

Reviewed on 13 May 2026

Opens in a new windowEcono Lodge Middlesboro
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.