Cumberland Gap Vacations

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Find the Best Cumberland Gap Vacation Packages

Cumberland Gap Hotel Deals

Pine Mountain State Resort Park

Pine Mountain State Resort Park

1050 State Park Road Pineville KY
Fully refundableReserve now, pay when you stay
NT$4,552
NT$5,018 total
Sep 4 - Sep 5
includes taxes & fees
9/10 Wonderful! (753 reviews)
"We enjoyed our stay in a clean and comfortable cabin. The park is beautiful."

Reviewed on 2026/8/28

Pine Mountain State Resort Park
Holiday Inn Express Middlesboro by IHG

Holiday Inn Express Middlesboro by IHG

1252 N 12th St Middlesboro KY
NT$4,139
NT$4,563 total
Aug 30 - Aug 31
includes taxes & fees
Holiday Inn Express Middlesboro by IHG
Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro

1260 N, 12th Street Middlesboro KY
Fully refundable
NT$3,198
NT$3,593 total
Sep 27 - Sep 28
includes taxes & fees
9.2/10 Wonderful! (922 reviews)
"Very friendly staff, great location. Perfect for our family trip."

Reviewed on 2026/8/27

Sleep Inn & Suites Middlesboro
See all 472 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.

Frequently asked questions

How much does a Cumberland Gap vacation package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a vacation to Cumberland Gap costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Cumberland Gap?
January, August and December are the best times to search for cheap Cumberland Gap vacation packages. Opting to travel in less busy months means you can usually find reduced prices on flights and accommodations.
How many days is enough for Cumberland Gap?
Typically, a handful of days is enough to explore the major attractions during your Cumberland Gap vacation. But if you'd like to have some time to chill out or go on day tours, consider extending your itinerary.
How to find the best Cumberland Gap package deals?
Finding a cheap Cumberland Gap package deal is a cinch with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, apply some filters and see what's available. You can personalize your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to view the most pocket-friendly Cumberland Gap package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Cumberland Gap vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll usually land a better deal than booking each component individually. And you'll still have the freedom to create a customized Cumberland Gap vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Cumberland Gap?
If you're considering an impromptu Cumberland Gap trip, check out 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 find terrific deals on your flights and hotels by booking ahead.
How to plan a trip to Cumberland Gap?
  1. Pick your dates: What you'd like to do in Cumberland Gap and your favorite season can help you decide when to go.
  2. Budget wisely: As well as the price of your accommodations, you'll need to consider other expenses too. These include transportation, flights and food. Also, set aside some extra funds for unexpected costs that may arise during your trip to Cumberland Gap.
  3. Decide your trip length: Consider how much time you'd like to spend exploring Cumberland Gap. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to pick a Cumberland Gap vacation package that brings all your bookings together.

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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.