Cumberland Gap Vacations from $845

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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.

The Latest Cumberland Gap vacation packages

Price found within the past 48 hours. Click for updated prices.
Americourt Extended Stays

Americourt Extended Stays

2 out of 5
Price was $875, price is now $845 per person
$845
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Tri-Cities (TRI)
4.2/10 (430 reviews)

The Downtown Post The Brady Suite

The Downtown Post The Brady Suite

4 out of 5
Price was $1,264, price is now $1,200 per person
$1,200
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Tri-Cities (TRI)
10/10 Exceptional! (3 reviews)
This was the perfect location. Close to restaurants, shopping and the covered bridge. The room was big and comfortable and it felt more like an apartment rather than a "hotel" room. Check-in was so easy as was the access to our room and parking. We will absolutely be back again in the spring to visit our daughter at Milligan University.

Reviewed on Oct 8, 2026

The Downtown Post The Gracie Suite

The Downtown Post The Gracie Suite

4 out of 5
Price was $1,192, price is now $1,137 per person
$1,137
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Tri-Cities (TRI)
No reviews
Loved The Gracie Suite! We absolutely loved our stay at The Downtown Post in The Gracie Suite! From the moment we arrived, it felt comfortable, welcoming, and peaceful. The suite was beautifully done, very clean, and had so much charm and character. It was one of those places where you immediately feel at home. Everything was thoughtfully put together, and we really appreciated the little details that made our stay extra enjoyable. We couldn't have asked for a better experience. We will definitely stay here again and won't hesitate to recommend "The Downtown Post" to family and friends. If you're considering booking it—do it! You won't be disappointed. ❤️ Thank you for such a wonderful stay!

Reviewed on Sep 7, 2026

The Downtown Post

The Downtown Post

2 out of 5
Price was $1,295, price is now $1,247 per person
$1,247
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Tri-Cities (TRI)
10/10 Exceptional! (1 review)

Motel 6 Kingsport, TN

Motel 6 Kingsport, TN

2 out of 5
Price was $914, price is now $882 per person
$882
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Tri-Cities (TRI)
8.2/10 Very Good! (1,003 reviews)
We had a nice stay. I travel with my boxer, Gibson, and it's not always easy to find a pet friendly place. While the motel is pet friendly, there are absolutely no outdoor accommodations for dogs. The room is the only thing that's pet friendly. We walked through the Arby's parking lot to a grassy knoll behind a local burger joint for the outdoor part. And it is a very basic room. Unless you consider microwave/mini fridge/color tv amenities there are no amenities. Not even a clock. Fresh towels, clean sheets, decent pillows, and two bars of soap. It's a Jack Reacher kind of room.

Reviewed on Nov 7, 2026

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Cumberland Gap Hotel Deals

The Olde Mill Inn Bed & Breakfast

The Olde Mill Inn Bed & Breakfast

2.5 out of 5
603 Pennlyn Avenue Cumberland Gap TN
Get rates
The Olde Mill Inn Bed & Breakfast
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Cumberland Gap TN
$176 nightly
The price is $198 total per night from Nov 19 to Nov 20
$198 total
Nov 19 - Nov 20
Total with taxes and fees
9.4/10 Exceptional! (52 reviews)
"This is my fourth stay at this property. We love the Cumberland Gap area. We will definitely be returning and specifically to this lovely house. The location is ideal. The hosts communication is great. Can’t say enough good things about our stay here."

Reviewed on Oct 6, 2026

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
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
$99 nightly
The price is $109 total per night from Nov 9 to Nov 10
$109 total
Nov 9 - Nov 10
Total with taxes and fees
Pine Mountain State Resort Park
See all 469 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.

Find the Best Cumberland Gap Vacation Packages

Cumberland Gap Essential Information

Language
English
Currency
U.S dollars
Population
490
Max Temp Winter
45ºF
Max Temp Summer
85ºF

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Frequently asked questions

What's included in a Cumberland Gap vacation package?
A Cumberland Gap vacation package lets you combine round-trip flights, hotel stays, and a rental car, providing a convenient way to explore this outdoor and nature destination. Many hotels in Cumberland Gap offer amenities like free breakfast, and some properties provide airport shuttle service to and from Knoxville, TN (TYS-McGhee Tyson).

Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
How can I save money on a Cumberland Gap vacation package?
When you bundle, you can save up to 30%*. To save money on a Cumberland Gap package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What are the top things to do in Cumberland Gap?
Cumberland Gap is an outdoor and nature destination, offering a mix of history, scenic beauty, and family fun for your Cumberland Gap vacation:

Browse and book things to do in Cumberland Gap on Expedia.
Do you need to rent a car in Cumberland Gap, or is public transport enough?
For a Cumberland Gap vacation package, a rental car offers the most flexibility for exploring this outdoor and nature destination. While Cumberland Gap National Historical Park is about a 10-minute walk from central Cumberland Gap, many other natural sights and family attractions are spread across the region.

A car allows you to easily reach places like Pine Mountain State Resort Park (about 6 miles away) for outdoor recreation, or family-friendly destinations such as Dollywood (about 18 miles). For travelers booking Cumberland Gap vacation packages with flights into airports like Knoxville, TN (TYS-McGhee Tyson) or Tri-Cities, TN (TRI-Tri-Cities Regional), picking up a rental car at the airport provides convenient access to the area and allows you to explore at your own pace. Your Cumberland Gap vacation package can be customized around these activities.
Can I change or cancel my Cumberland Gap vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Cumberland Gap vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Cumberland Gap vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Cumberland Gap vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Cumberland Gap?
To find last-minute vacation packages to Cumberland Gap, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Cumberland Gap vacation packages?
Free cancellation on a Cumberland Gap vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Cumberland Gap vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Cumberland Gap getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Cumberland Gap vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

Explore a world of travel with Expedia

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