Cumberland Gap Holidays

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Cumberland Gap Holiday

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

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Cumberland Gap TN
9.4/10 Exceptional! (48 reviews)
"Great place to stay."

Reviewed on 21 June 2026

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Cozy Cumberland Gap Cottage Near LMU & Nat’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 AU$170 per night from 20 Aug to 21 Aug
AU$170
20 Aug - 21 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 AU$98 per night from 25 Aug to 26 Aug
AU$98
25 Aug - 26 Aug
includes taxes & fees
7.2/10 Good! (1,000 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 473 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
All Inclusive Holidays
Cheap Holidays
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beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Cumberland Gap holiday package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a holiday 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 holiday packages. Opting to travel in less busy months means you can usually find reduced prices on flights and accommodation.
How many days is enough for Cumberland Gap?
Typically, a handful of days is enough to explore the major attractions during your Cumberland Gap holiday. 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 personalise 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 holiday as a package?
Expedia holiday 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 customised Cumberland Gap holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday 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 favourite season can help you decide when to go.
  2. Budget wisely: As well as the price of your accommodation, 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 holiday package that brings all your bookings together.

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