Cumberland Gap Vacations

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Find the Best Cumberland Gap Vacation Packages

Cumberland Gap Hotel Deals

Cozy Cumberland Gap Cottage Near LMU & Natā€™l Park

Cozy Cumberland Gap Cottage Near LMU & Natā€™l Park

Cumberland Gap TN
The price is SARĀ 560 per night from Jul 22 to Jul 23
SARĀ 560
SARĀ 1,032 total
22 Jul - 23 Jul
includes taxes & fees
9.4/10 Exceptional! (48 reviews)
"Great place to stay."

Reviewed on 21 June 2026

Cozy Cumberland Gap Cottage Near LMU & Natā€™l Park
Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro

2.5 out of 5
1260 N, 12th Street Middlesboro KY
Fully refundable
The price is SARĀ 396 per night from Aug 19 to Aug 20
SARĀ 396
SARĀ 444 total
19 Aug - 20 Aug
includes taxes & fees
9.2/10 Wonderful! (905 reviews)
"Top rating in all regards. Quiet on top of a small hill by itself, surrounded by trees."

Reviewed on 18 July 2026

Sleep Inn & Suites Middlesboro
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 SARĀ 229 per night from Jul 28 to Jul 29
SARĀ 229
SARĀ 262 total
28 Jul - 29 Jul
includes taxes & fees
7.2/10 Good! (1,004 reviews)
"No towels in room when we arrived no pillow cases on pillows the pillows were stained. No hot water in the morning no cream and sugar for the coffee. Dust everywhere in the room. Pool non operational. Place was dirty gutters falling off building trash outside rooms blowing everywhere. Really sad ..."

Reviewed on 19 July 2026

Days Inn by Wyndham Jellico - Tennessee State Line
See all 475 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?
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 ā€” ideal for budget-conscious travelers.
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 favorite 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.