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.

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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 $185 per night from Aug 3 to Aug 4
CA $185
CA $209 total
Aug 3 - Aug 4
includes taxes & fees
9.6/10 Exceptional! (160 reviews)
"Very accommodating, delicious food and friendly environment, beautiful area"

Reviewed on Jul. 14, 2025

The 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 CA $136 per night from Aug 17 to Aug 18
CA $136
CA $150 total
Aug 17 - Aug 18
includes taxes & fees
9/10 Wonderful! (585 reviews)
Comfortable Family Stay
"We stayed in one of the cottages with our son and his 5 year old son. There were 2 bedrooms, each with 2 queen size beds, and a tv and bathroom for each bedroom. It had a large area to include the kitchen, eating area and living room. It had a balcony overlooking the woods with table and chairs."

Reviewed on Jul. 22, 2025

Pine Mountain State Resort Park
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
Fully refundableReserve now, pay when you stay
The price is CA $90 per night from Aug 3 to Aug 4
CA $90
CA $103 total
Aug 3 - Aug 4
includes taxes & fees
7.2/10 Good! (973 reviews)
"A quick overnight visit on the way to vacation destination. It was quiet and comfortable although there’s major remodeling going on the front desk clerk was super nice and helpful."

Reviewed on Jul. 22, 2025

Days Inn by Wyndham Jellico - Tennessee State Line
See all 423 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?
You'll find cheap prices on Expedia for your Cumberland Gap escape. However, factors like the season, length of stay and your choice of hotel will determine how much your vacation to Cumberland Gap costs.
What are the cheapest months to go to Cumberland Gap?
If you'd like to book a cheap Cumberland Gap vacation package, consider visiting in January, August and December. You're likely to find lower rates on airfares and hotels during these months — ideal for budget-conscious travellers.
How many days is enough for Cumberland Gap?
The ideal duration of your Cumberland Gap vacation depends on what you'd like to do. Usually, a handful of days to a week will give you enough time to tick off all the top sights and explore some hidden gems along the way.
How to find the best Cumberland Gap package deals?
Start your search for a Cumberland Gap package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select some filters, like "Popular locations" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Cumberland Gap package deal right away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Cumberland Gap escape off to a flying start.
Is it cheaper to book a Cumberland Gap vacation as a package?
You can enjoy significant savings on your next Cumberland Gap getaway by booking a customized vacation package. Check the "Package" heading, then enter your destination and travel dates to browse the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Cumberland Gap?
If you're considering an impromptu Cumberland Gap trip, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score incredible deals on your flights and hotels by booking ahead.
How to plan a trip to Cumberland Gap?

  1. Choose when to travel: Check your schedule and pack your bags. Your favourite season and the activities available will also help you decide when to visit Cumberland Gap.
  2. Set a budget: Consider costs like flights, food and transportation when working out how much to save for your trip to Cumberland Gap. Then, select a property that suits your budget, whether that's an affordable stay or a high-end getaway.
  3. Decide how long to go for: Now that you know more about Cumberland Gap, you can work out the right length of your break. Put together a rough itinerary and give yourself enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a personalized Cumberland Gap vacation package.

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