Middlesboro Holiday Packages

Save when you book Middlesboro package deals

Choose two or more items and save on your trip:

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 Middlesboro

Sleep Inn & Suites Middlesboro

2.5 out of 5
1260 N, 12th Street Middlesboro KY
Fully refundable
The price is AU$155 per night from 16 Feb to 17 Feb
AU$155
per night
16 Feb - 17 Feb
Sleep Inn & Suites Middlesboro: Pet-friendly hotel with free breakfast and free WiFi. Located in the city centre.
Belinda at the desk is amazing She made our stay excellent , she made us feel like we were old friends . We will be staying here on each visit .

Reviewed on 24 Jan 2026

Opens in a new windowSleep Inn & Suites Middlesboro
Holiday Inn Express Williamsburg by IHG

Holiday Inn Express Williamsburg by IHG

2.5 out of 5
56 West Highway 92 Williamsburg KY
Fully refundable
The price is AU$194 per night from 23 Feb to 24 Feb
AU$194
per night
23 Feb - 24 Feb
Holiday Inn Express Williamsburg by IHG: Pet-friendly hotel with free breakfast and free WiFi. Located in the mountains.
Pleasant front desk staff. Room was clean spacious room with comfortable bedding. Continental breakfast was decent and always comes in handy! Located close to Walmart and fast food restaurants for quick shopping and dining.

Reviewed on 7 Feb 2026

Opens in a new windowHoliday Inn Express Williamsburg by IHG
Boone Trail Inn

Boone Trail Inn

2 out of 5
2105 US HIGHWAY 25 E Middlesboro KY
Fully refundableReserve now, pay when you stay
The price is AU$119 per night from 11 Feb to 12 Feb
AU$119
per night
11 Feb - 12 Feb
Boone Trail Inn: Pet-friendly motel with free WiFi and free parking. Guests love the helpful staff!
The owners and staff were quite nice. The owner brought me a blanket without me having to ask since the temp was going to drop into the 40s. Inside,the owners have done an excellent update of the rooms.Excellent value for the money.

Reviewed on 21 Oct 2025

Opens in a new windowBoone Trail Inn
Don't see what you're looking for?
See all available properties in Middlesboro
View all properties
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.