Cumberland Gap Trips (flight + hotel)

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Top hotels in Cumberland Gap

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 P7,693 per night from Aug 10 to Aug 11
P7,693
P8,712 total
Aug 10 - Aug 11
includes taxes & fees
9.6/10 Exceptional! (163 reviews)
"Very accommodating, delicious food and friendly environment, beautiful area"

Reviewed on Jul 14, 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
The price is P6,698 per night from Aug 23 to Aug 24
P6,698
P7,384 total
Aug 23 - Aug 24
includes taxes & fees
8.8/10 Excellent! (587 reviews)
"Setting was stunning. Staff nice. Food was okay. Prefer healthy menu options. I purchased two candy bars from the front desk and they were both grey when I opened them. They were supposed to be chocolate. When I went back the next morning the lady at the front desk said ‘oh, sorry’ not offering me ..."

Reviewed on Jul 29, 2025

Pine Mountain State Resort Park
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 P5,900 per night from Sep 1 to Sep 2
P5,900
P6,504 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (758 reviews)
"The hotel is off the main road and was so quiet despite being fully booked. The staff was so incredibly friendly. I loved my stay here!"

Reviewed on Jul 25, 2025

Sleep Inn & Suites
See all 421 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.

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