Cumberland Gap Holidays

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Your Cumberland Gap Holiday

Select a Cumberland Gap holiday package and focus on what matters — enjoying yourself. This means no more stressful planning, just lots more time to savour 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 holiday is only clicks away with Expedia.

Cumberland Gap Essential Information

Language
English
Currency
U.S dollars
Population
490
Max Temp Winter
7ºC
Max Temp Summer
29ºC
Top Sights
Pine Mountain State Resort Park, Bell County Historical Society Museum and Middlesboro Mall

Our pick of the best 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
Stay at this B&B in Cumberland Gap. Enjoy free breakfast, free parking and conference space. Our guests praise the breakfast in their reviews. Popular attractions ...
9.6/10 Exceptional! (160 reviews)
"Amazing!!!! The room was gorgeous and very clean. Much love and care has obviously been put into this B&B. Breakfast was wonderful. Staff was thoughtful and friendly. Their attention to detail is unmatched! We will definitely be back!!!"

Reviewed on 20 Jun 2025

The Olde Mill Inn Bed & Breakfast
Days Inn by Wyndham Jellico - Tennessee State Line
Days Inn by Wyndham Jellico - Tennessee State Line
2 out of 5
1417 5th Street, Jellico, TN
Stay at this spa hotel in Jellico. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms in their reviews. ...
7.2/10 Good! (959 reviews)
"The lawn needed to be mowed, more chairs at the pool, trash in the grassy areas, ants in the room next to ours. Staff was very friendly."

Reviewed on 25 May 2025

Days Inn by Wyndham Jellico - Tennessee State Line
Pine Mountain State Resort Park
Pine Mountain State Resort Park
3 out of 5
1050 State Park Road, Pineville, KY
Stay at this 3-star golf hotel in Pineville. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular ...
8.8/10 Excellent! (568 reviews)
"Love this park. Every time I want to come to Kentucky I want to go there. Have a wonderful pool. The staff is always friendly. We have never had any problems. We have stayed here a couple of times"

Reviewed on 22 Jun 2025

Pine Mountain State Resort Park
See all 415 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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Cumberland Gap travel package cost?
Our Cumberland Gap travel packages, which begin at just , are an awesome way to save money. Pick and choose your preferred hotels, flights and rental car to create a personalized escape.
If I'm not able to travel, can I cancel my Cumberland Gap travel package?
Plans can change in a flash, so yes. You may be able to cancel and rebook your Cumberland Gap travel package for free within 24 hours of booking. For bookings made more than 24 hours ago, you can still cancel and rebook, but your airline, hotel or car rental company may charge a fee. Looking for more information? Visit our Customer Service Portal. We'll help make sure your getaway goes off without a hitch.
How do I get a cheap travel package to Cumberland Gap?
Bundle your flights and hotels, add extras such as tours, and save with a Cumberland Gap travel package. You won't just pick up impressive discounts on your adventure --- you'll have loads of choice at your fingertips too. When you book through Expedia, you'll have your pick of over 550 airlines and 1,000,000 properties all over the world. Your next grand adventure starts right here, right now!
Does Expedia offer Book Now, Pay Later Cumberland Gap holidays?
Expedia has teamed up with online lender Klarna to make booking your next break easier on your wallet. Paying by instalment means you can spread the costs of your dream holiday, leaving you with more cash to play with while you're away. Klarna has several payment plans to pick from, so you're sure to find one that works with your budget. Consider these flexible payment options:

  • Pay monthly holidays: If paying bite-sized amounts each month sounds right for you, Klarna offers just that! Paying in convenient monthly instalments will make your getaway dreams come true.
  • Pay in instalments holidays: Like the idea of paying off your holiday in multiple transactions? Then check out this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: Pressing the "book now" button is easier with this plan. Put down a small deposit on your booking and then start working on your travel itinerary.

What are the top hotels in Cumberland Gap?
Best Western Plus Music Row and Gaylord Opryland Resort & Convention Centre are among the most sought-after properties in Cumberland Gap. Why not look up the facilities and rates at each and then decide?
How far in advance should I book my Cumberland Gap holiday?
To score cheap prices, book early. Airlines generally advertise flights, along with some of the lowest fares, around 12 months in advance. Hotels, car rental and experiences should also be booked well in advance to avoid disappointment. If you've decided on a last-minute getaway to Cumberland Gap, there are always lots of great bargains to be had on Expedia. Book your escape today!
What does an Expedia Cumberland Gap travel package include?
Hotels, flights and rental cars, or any combination of the three --- it's your choice. Whether you're headed to Cumberland Gap on a family road trip or travelling by yourself, there's a bundle to fit your style and budget. Once you've made your booking, why not add on some tours and experiences?
What should I know before booking a Cumberland Gap travel package?
You can save a tidy sum by combining your flights, hotels and rental cars. Once you've made your booking, you can add on things like sightseeing tours or experiences. Your next awesome holiday is only a few clicks away.
Can I choose my airline with a Cumberland Gap Expedia travel package?
With a travel package, you're the boss. Whether you'd prefer to fly to Cumberland Gap in economy or business class, simply choose from the available airline options. Expedia has access to over 550 partner airlines worldwide.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.