Cumberland Gap Vacations

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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
$130 nightly
The price is $148 total per night from Oct 29 to Oct 30
$148 total
Oct 29 - Oct 30
Total with taxes and fees
9.6/10 Exceptional! (173 reviews)
best

Reviewed on Oct 15, 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
$88 nightly
The price is $97 total per night from Oct 29 to Oct 30
$97 total
Oct 29 - Oct 30
Total with taxes and fees
9/10 Wonderful! (639 reviews)
Th views are amazing, great service and property. We will be back!

Reviewed on Oct 23, 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
$63 nightly
The price is $72 total per night from Oct 29 to Oct 30
$72 total
Oct 29 - Oct 30
Total with taxes and fees
7/10 Good! (1,000 reviews)
Pool was green

Reviewed on Oct 17, 2025

Days Inn by Wyndham Jellico - Tennessee State Line
See all 447 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.

Find the Best Cumberland Gap Vacation Packages

Cumberland Gap Essential Information

Language
English
Currency
U.S dollars
Population
490
Max Temp Winter
45ºF
Max Temp Summer
85ºF

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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?
You can generally find lower prices and better availability in January, June and December. Take a look at our cheap Cumberland Gap vacation packages and you could score some excellent off-season deals.
How many days is enough for Cumberland Gap?
Generally, a handful of days is enough to go to the major sights during your Cumberland Gap vacation. But if you want to have more time to unwind 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.
Does Expedia offer Book Now, Pay Later Cumberland Gap vacation packages?
Your Cumberland Gap trip should be a relaxing escape from your busy life, not a reason for money worries. So to give you that extra flexibility, we've teamed up with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.

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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.