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

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$163 per night from 20 Apr to 21 Apr
AU$163
includes taxes & fees
20 Apr - 21 Apr
Sleep Inn & Suites: Pet-friendly hotel with free breakfast and free WiFi. Located in the city centre.
"Is good if the facility bring coffe al day."

Reviewed on 30 Mar. 2025

Sleep 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$150 per night from 20 Apr to 21 Apr
AU$150
includes taxes & fees
20 Apr - 21 Apr
Econo Lodge Middlesboro: Pet-friendly motel with free breakfast and free WiFi. Located in the mountains.
"Easy check in. Very quiet. Convenient to resteraunts"

Reviewed on 31 Mar. 2025

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

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

Middlesboro
The price is AU$340 per night from 7 Apr to 8 Apr
AU$340
includes taxes & fees
7 Apr - 8 Apr
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky, : Holiday home with free WiFi and parking.
Uncle Ernie's lovely Lustron
"Perfect! Owner was awesome and incredibly responsive. The house was immaculate and ideal for us. Wish we could have enjoyed the fire pit too but we were able to stay high and dry and cozy in the house and avoid the torrential downpours. There is even a nice covered area to get to the carport from ..."

Reviewed on 18 Mar. 2025

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