Cumberland Gap Holidays

Book a Hotel + Flight or Car together to unlock savings

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 3.523.075 ₫ per night from 24 Aug to 25 Aug
3.523.075 ₫
3.989.928 ₫ total
24 Aug - 25 Aug
includes taxes & fees
9.6/10 Exceptional! (166 reviews)
"loved the historical setting, walking distance to shops, parks, hiking trails."

Reviewed on 10 Aug 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 3.067.519 ₫ per night from 22 Aug to 23 Aug
3.067.519 ₫
3.381.732 ₫ total
22 Aug - 23 Aug
includes taxes & fees
9/10 Wonderful! (592 reviews)
"Beautiful lodge. Wonderful room with view of the moutians. Dinner available on site. Went to the pool this time and very nice."

Reviewed on 10 Aug 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 2.456.619 ₫ per night from 31 Aug to 1 Sept
2.456.619 ₫
2.708.177 ₫ total
31 Aug - 1 Sept
includes taxes & fees
9/10 Wonderful! (761 reviews)
"a"

Reviewed on 14 Aug 2025

Sleep Inn & Suites
See all 423 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 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.