Middlesboro Holiday Packages

Save when you book Middlesboro package deals

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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

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$164 per night from 16 Feb to 17 Feb
AU$164
includes taxes & fees
16 Feb - 17 Feb
Sleep Inn & Suites: Pet-friendly hotel with free breakfast and free WiFi. Located in the city centre.
"Saw (and smelled) a few fragrance plugins, no hotel should have these. I unplugged the one in my room."

Reviewed on 27 Jan. 2025

Sleep Inn & Suites
Holiday Inn Express Williamsburg, an IHG Hotel

Holiday Inn Express Williamsburg, an IHG Hotel

2.5 out of 5
56 West Highway 92, Williamsburg, KY
Fully refundable
The price is AU$169 per night from 10 Feb to 11 Feb
AU$169
includes taxes & fees
10 Feb - 11 Feb
Holiday Inn Express Williamsburg, an IHG Hotel: Pet-friendly hotel with free breakfast and free WiFi. Located in the mountains.
"Conveniently located near I-75 and was a nice stop while traveling."

Reviewed on 31 Jan. 2025

Holiday Inn Express Williamsburg, an IHG Hotel
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$159 per night from 9 Feb to 10 Feb
AU$159
includes taxes & fees
9 Feb - 10 Feb
Econo Lodge Middlesboro: Pet-friendly motel with free breakfast and free WiFi. Located in the mountains.
Good for the price
"Great cozy rooms..pillows suck"

Reviewed on 5 Jan. 2025

Econo 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.