Cumberland Gap Holiday Packages

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You work so hard for your money, so don't let it go down the plughole — Wotif is here to help.

It doesn't get easier than one of our flight and accommodation packages.

This way, you'll have some extra funds for your trip to Cumberland Gap.

So, what's holding you back? Book soon and save up to . Simply pick and choose from more than 550 partner airlines and 665,000 worldwide properties.

Don't waste time staring at a screen when you really should be hitting the tarmac. Wotif offers some of the top prices anywhere.

Cumberland Gap Accommodation

Looking forward to your well-earned holiday? Wotif currently offers some wonderful places to rest your head at night. But with just 3 accommodations in Cumberland Gap, the best deals are reserved for those who book in early.

Should have booked your accommodation by now? Left it to the last moment? Don't panic — we've got your back. Check out The Olde Mill Inn Bed & Breakfast (603 Pennlyn Avenue) or the Sleep Inn & Suites (1260 N, 12th Street).

Car Hire in Cumberland Gap

It's an easy taxi drive from Moore-Murrell Airport to Enterprise (4871 W Andrew Johnson Hwy). You'll have your luggage in the back and your gang on the road before you know it.

Holidays to Cumberland Gap

Enjoy going to places you've never been before? Us too. But there's no need to get yourself lost along the way. Look over our guide to Cumberland Gap and you'll be strolling around like a proper local before you know it.

Cumberland Gap has a couple of cities on its doorstep. From the centre, Middlesboro is 10 kilometres away to the north. You can also easily get to Williamsburg, which is 45 kilometres to the northwest.

Whether you're interested in statistics or not, it never hurts to know how many people inhabit the place you're going to. In this area of Eastern Tennessee, the population is approximately 500.

Top Cumberland Gap hotels

The Olde Mill Inn Bed & Breakfast

The Olde Mill Inn Bed & Breakfast

2.5 out of 5
603 Pennlyn Avenue Cumberland Gap TN
The price is AU$198 per night from 27 Feb to 28 Feb
AU$198
27 Feb - 28 Feb
includes taxes & fees
The Olde Mill Inn Bed & Breakfast: Bed & breakfast with free breakfast and free WiFi.
The staff was excellent. They are wonderful people. They made sure everything was perfect. We enjoyed having breakfast with the other guests. They addressed any allergy concerns and tailored your breakfast for all. I would recommend this bed and breakfast it is the best one we have ever stayed ...

Reviewed on 18 Jan 2026

Opens in a new windowThe Olde Mill Inn Bed & Breakfast
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$157 per night from 23 Feb to 24 Feb
AU$157
23 Feb - 24 Feb
includes taxes & fees
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
Pine Mountain State Resort Park

Pine Mountain State Resort Park

3 out of 5
1050 State Park Road Pineville KY
Fully refundableReserve now, pay when you stay
Pine Mountain State Resort Park: Pet-friendly hotel with free WiFi and free parking. Located in a state park.
Cabin was clean and well furnished

Reviewed on 21 Jan 2026

Opens in a new windowPine Mountain State Resort Park
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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.