Cumberland Gap Vacation Packages

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Your Cumberland Gap Vacation

Select a Cumberland Gap vacation package and focus on what matters — enjoying yourself. This means no more stressful planning, just lots more time to savor the delights of this lively city, such as its rich history and spectacular views. If your trip to Cumberland Gap includes a little sightseeing, visit popular attractions like Cumberland Gap National Historical Park, Middlesboro Mall and Bell County Historical Society Museum. Whoever you're heading away with and whatever you want to spend, your dream Cumberland Gap vacation is only clicks away with Expedia.

Cumberland Gap Hotel Deals

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 CA $193 per night from Jun. 12 to Jun. 13
CA $193
CA $219 total
includes taxes & fees
Jun 12 - Jun 13
9.4/10 Exceptional! (126 reviews)
Beautiful private window with a view.
"The room was lovely and the view from the bed has a huge window looking toward the mountain. The window is totally private so you can leave the curtains open and wake up to a beautiful day."

Reviewed on May 30, 2024

The Olde Mill Inn Bed & Breakfast
Cumberland Gap Inn
Cumberland Gap Inn
2.5 out of 5
630 Brooklyn Street, Cumberland Gap, TN
7.8/10 Good! (540 reviews)
"This was a great place tucked away in the hills. We are grateful they were pwt friendly and even had a back door to our room with a patio"

Reviewed on Apr. 21, 2024

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Cumberland Gap Inn
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 CA $148 per night from Jun. 23 to Jun. 24
CA $148
CA $163 total
includes taxes & fees
Jun 23 - Jun 24
9/10 Wonderful! (566 reviews)
"Great place to stay when traveling on our motorcycle"

Reviewed on May 26, 2024

Sleep Inn & Suites
See all 403 properties in Cumberland Gap
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.

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Frequently asked questions

How much does a Cumberland Gap vacation package cost?
The cheapest Cumberland Gap vacation package is , so your dream trip can become a reality — without spending an arm and a leg. Combine flights, hotels, car rentals and more to create a package that matches your traveling style.
How do I get a cheap travel package to Cumberland Gap?
One of the simplest ways to save money (and time) is to combine your bookings with Expedia. Hotels, rental cars, flights and activities — we’ve got them all covered. Select a combination that suits your style and watch your savings grow. We know a package deal is never one-size-fits-all. That’s why we offer over 550 airlines and 1,000,000 properties across the globe, which lets you customize your Cumberland Gap vacation.
Where should I stay in Cumberland Gap?
A getaway to Cumberland Gap isn’t complete without paying a visit to Middlesboro Mall. Why not stay near this interesting tourist attraction?
What are the top hotels in Cumberland Gap?
The Olde Mill Inn Bed And Breakfast and Cumberland Gap Inn are a couple of the most well-known properties in Cumberland Gap. Why not check out the rates and facilities at each and then make up your mind?
How far in advance should I book my Cumberland Gap vacation?
It depends on the airline, but you can generally look up international fares on Expedia nearly a year in advance. While it’s advisable to book ahead of time, lucky travelers occasionally nab a cheaper seat only weeks before the date of departure.
What does an Expedia Cumberland Gap travel package include?
Hotels, flights and rental cars, or any combination of the three — you decide! Whether you’re headed to Cumberland Gap with the family or traveling with your friends, there’s a bundle to match every style and budget. Once you’ve made your booking, why not add on a couple of tours as well?
What should I know before booking a Cumberland Gap travel package?
A package can be easier on the credit card than separately booking everything you need for your adventure. For example, combine your hotels, flights and rental cars and save big. Whatever kind of vacation you’re planning, you’ll find a package that suits your budget.
Can I choose my airline with a Cumberland Gap Expedia vacation package?
Yes, definitely. Expedia has more than 550 airline partners to select from all over the world. With such a big range of choice, finding the perfect carrier to take you to Cumberland Gap will be easy.
If I'm not able to travel, can I cancel my Cumberland Gap vacation package?
Yes, it’s possible to cancel your Cumberland Gap booking if your plans have been upended. Whether you’ll incur a fee or not depends on your hotel, airline or car rental company. You may be able to cancel or change for free if you booked in the last 24 hours. Visit our Customer Service Portal for more information.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.