Cumberland Gap Vacations

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Find the Best Cumberland Gap Vacation Packages

Cumberland Gap Hotel Deals

Cumberland Gap Inn
Cumberland Gap Inn
2.5 out of 5
630 Brooklyn Street, Cumberland Gap, TN
Fully refundableReserve now, pay when you stay
The price is AED 360 per night from Apr 1 to Apr 2
AED 360
AED 408 total
includes taxes & fees
1 Apr - 2 Apr
7.8/10 Good! (560 reviews)
"The man at the front desk was very polite and helpful. He attended to all our needs. We will definitely stay there the next time we come to town."

Reviewed on 26 March 2025

Cumberland Gap Inn
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 AED 547 per night from Apr 1 to Apr 2
AED 547
AED 620 total
includes taxes & fees
1 Apr - 2 Apr
9.6/10 Exceptional! (152 reviews)
"It's great"

Reviewed on 21 March 2025

The Olde Mill Inn Bed & Breakfast
Sleep Inn & Suites
Sleep Inn & Suites
2.5 out of 5
1260 N, 12th Street, Middlesboro, KY
Fully refundableReserve now, pay when you stay
The price is AED 343 per night from Apr 13 to Apr 14
AED 343
AED 379 total
includes taxes & fees
13 Apr - 14 Apr
9/10 Wonderful! (697 reviews)
"No big amenities but it is a quiet and nicely appointed hotel. Hot breakfast was very good. Front desk staff were nice. Would definitely stay again."

Reviewed on 24 March 2025

Sleep Inn & Suites
See all 407 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 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.