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$235 per night from 3 Aug to 4 Aug
AU$235
3 Aug - 4 Aug
includes taxes & fees
The Olde Mill Inn Bed & Breakfast: Bed & breakfast with free breakfast and free WiFi.
"Very accommodating, delicious food and friendly environment, beautiful area"

Reviewed on 14 Jul. 2025

The Olde Mill Inn Bed & Breakfast
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$181 per night from 1 Sept to 2 Sept
AU$181
1 Sept - 2 Sept
includes taxes & fees
Sleep Inn & Suites: Pet-friendly hotel with free breakfast and free WiFi. Located in the city centre.
"The hotel is off the main road and was so quiet despite being fully booked. The staff was so incredibly friendly. I loved my stay here!"

Reviewed on 25 Jul. 2025

Sleep Inn & Suites
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$199 per night from 23 Aug to 24 Aug
AU$199
23 Aug - 24 Aug
includes taxes & fees
Pine Mountain State Resort Park: Pet-friendly hotel with free WiFi and free parking. Located in a state park.
"Setting was stunning. Staff nice. Food was okay. Prefer healthy menu options. I purchased two candy bars from the front desk and they were both grey when I opened them. They were supposed to be chocolate. When I went back the next morning the lady at the front desk said ‘oh, sorry’ not offering me ..."

Reviewed on 29 Jul. 2025

Pine 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.