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 Olde Mill Inn Bed & Breakfast: Bed & breakfast with free breakfast and free WiFi.
We enjoyed this cozy bed and breakfast. It's a great location - so beautiful! The staff was amazing - we had a meeting at LMU and were missing breakfast. So they packed us a breakfast and put it in the common area refrigerator for us to grab in the morning. It was also handy to fill our cups with ...

Reviewed on 2 Mar 2026

Opens in a new windowThe Olde Mill Inn Bed & Breakfast
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
The price is AU$144 per night from 17 Apr to 18 Apr
AU$144
17 Apr - 18 Apr
includes taxes & fees
Pine Mountain State Resort Park: Pet-friendly hotel with free WiFi and free parking. Located in the mountains.
Complementary breakfast

Reviewed on 5 Apr 2026

Opens in a new windowPine Mountain State Resort Park
Cumberland Gap Inn

Cumberland Gap Inn

2.5 out of 5
630 Brooklyn Street Cumberland Gap TN
Cumberland Gap Inn: Pet-friendly motel with free WiFi and free parking. Located in a state park.
Opens in a new windowCumberland Gap Inn
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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.