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
Fully refundable
The price is AU$210 per night from 21 Sept to 22 Sept
AU$210
21 Sept - 22 Sept
includes taxes & fees
Holiday Inn Express Middlesboro by IHG: Business-friendly hotel with free breakfast and free WiFi. Located in the mountains.
"Very clean and loved that Dove products were supplied"

Reviewed on 31 Aug. 2025

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

Sleep Inn & Suites

2.5 out of 5
1260 N, 12th Street, Middlesboro, KY
Fully refundableReserve now, pay when you stay
The price is AU$153 per night from 9 Oct to 10 Oct
AU$153
9 Oct - 10 Oct
includes taxes & fees
Sleep Inn & Suites: Pet-friendly hotel with free breakfast and free WiFi. Located in the city centre.
"Staff were terrific. We rode motorcycles and it was pouring rain. They gave us each garbage bags to cover our bags. The elevator was down and I know they were getting some complaints but they were still very helpful and pleasant."

Reviewed on 4 Sep. 2025

Opens in a new windowSleep Inn & Suites
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$140 per night from 14 Sept to 15 Sept
AU$140
14 Sept - 15 Sept
includes taxes & fees
Econo Lodge Middlesboro: Pet-friendly motel with free breakfast and free WiFi. Located in the mountains.
"Stopped up drain in tub. Otherwise okay for overnight stay."

Reviewed on 28 Aug. 2025

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.