Cumberland Gap Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Cumberland Gap Vacation
Select a Cumberland Gap vacation package and focus on what matters — enjoying yourself. This means no more stressful planning, just lots more time to savor the delights of this lively city, such as its rich history and spectacular views. If your trip to Cumberland Gap includes a little sightseeing, visit popular attractions like Cumberland Gap National Historical Park, Middlesboro Mall and Bell County Historical Society Museum. Whoever you're heading away with and whatever you want to spend, your dream Cumberland Gap vacation is only clicks away with Expedia.
Top Cumberland Gap Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Mountain Harbour B&B and Hiker Hostel
CA $1,085
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tri-Cities (TRI)
9.4/10 Exceptional! (117 reviews)
We always feel welcome at Mountain Harbour - the breakfast is exceptional, and the hosts are lovely people who go above and beyond for their guests. Thanks for another great stay!
Reviewed on Jan 21, 2026
The Bristol Hotel
CA $1,590
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Tri-Cities (TRI)
9.8/10 Exceptional! (1,011 reviews)
Very nicely appointed, clean and comfortable property. Would definitely stay again!! Rooftop bar was a plus! Great location
Reviewed on Sep 2, 2026
Ready to book your vacation to Cumberland Gap?
Cumberland Gap Hotel Deals
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
Cumberland Gap TN
9.4/10 Exceptional! (51 reviews)
"We had a great stay. The property was exactly as described: clean, comfortable, and well-maintained. Check-in was easy, and everything met our expectations. We would gladly stay here again."
Reviewed on Aug 18, 2026
Days Inn by Wyndham Jellico - Tennessee State Line
1417 5th Street Jellico TN
Fully refundableReserve now, pay when you stay
CA $82
CA $94 total
Sep 6 - Sep 7
includes taxes & fees
Sleep Inn & Suites Middlesboro
1260 N, 12th Street Middlesboro KY
Fully refundable
CA $140
CA $157 total
Sep 27 - Sep 28
includes taxes & fees
9.2/10 Wonderful! (927 reviews)
"Clean room, comfy bed…worked for us just passing through for the night. Staff was great."
Reviewed on Sep 2, 2026
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?
You'll find cheap prices from CA $1,085 on Expedia for your Cumberland Gap escape. However, factors like the season, length of stay and your choice of hotel will determine how much your vacation to Cumberland Gap costs.
What are the cheapest months to go to Cumberland Gap?
If you'd like to book a cheap Cumberland Gap vacation package, consider visiting in January, August and December. You're likely to find lower rates on airfares and hotels during these months — ideal for budget-conscious travellers.
How many days is enough for Cumberland Gap?
The ideal duration of your Cumberland Gap vacation depends on what you'd like to do. Usually, a handful of days to a week will give you enough time to tick off all the top sights and explore some hidden gems along the way.
How to find the best Cumberland Gap package deals?
Start your search for a Cumberland Gap package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select some filters, like "Popular locations" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Cumberland Gap package deal right away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Cumberland Gap escape off to a flying start.
Is it cheaper to book a Cumberland Gap vacation as a package?
You can enjoy significant savings on your next Cumberland Gap getaway by booking a customized vacation package. Check the "Package" heading, then enter your destination and travel dates to browse the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Cumberland Gap?
If you're considering an impromptu Cumberland Gap trip, browse 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 score incredible deals on your flights and hotels by booking ahead.
How to plan a trip to Cumberland Gap?
- Choose when to travel: Check your schedule and pack your bags. Your favourite season and the activities available will also help you decide when to visit Cumberland Gap.
- Set a budget: Consider costs like flights, food and transportation when working out how much to save for your trip to Cumberland Gap. Then, select a property that suits your budget, whether that's an affordable stay or a high-end getaway.
- Decide how long to go for: Now that you know more about Cumberland Gap, you can work out the right length of your break. Put together a rough itinerary and give yourself enough time to cover everything you want to do.
- Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a personalized Cumberland Gap vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
