Cumberland Gap Holidays

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    Save up to S$134 when you book a flight and hotel together*
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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 S$217 per night from 23 Jun to 24 Jun
S$217
23 Jun - 24 Jun
includes taxes & fees
9.6/10 Exceptional! (160 reviews)
"Amazing!!!! The room was gorgeous and very clean. Much love and care has obviously been put into this B&B. Breakfast was wonderful. Staff was thoughtful and friendly. Their attention to detail is unmatched! We will definitely be back!!!"

Reviewed on 20 Jun, 2025

The Olde Mill Inn Bed & Breakfast
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 S$121 per night from 25 Jun to 26 Jun
S$121
25 Jun - 26 Jun
includes taxes & fees
7.2/10 Good! (958 reviews)
"The lawn needed to be mowed, more chairs at the pool, trash in the grassy areas, ants in the room next to ours. Staff was very friendly."

Reviewed on 25 May, 2025

Days Inn by Wyndham Jellico - Tennessee State Line
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 S$172 per night from 28 Jun to 29 Jun
S$172
28 Jun - 29 Jun
includes taxes & fees
8.8/10 Excellent! (567 reviews)
"Great cabin in a beautiful state park"

Reviewed on 17 Jun, 2025

Pine Mountain State Resort Park
See all 415 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.