Cumberland Gap Vacations from $430

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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.
Motel 6 Bristol, VA

Motel 6 Bristol, VA

2 out of 5
Price was $474, price is now $430 per person
$430
per person
Oct 25 - Oct 28
found 3 hours ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Tri-Cities (TRI)
8.6/10 Excellent! (1,005 reviews)
Beatiful place and very efficient personal. Very cozy and comfortable place. Will stay only here, and highly recommend it to all of my friends.

Reviewed on Aug 24, 2025

Mountain Harbour B&B and Hiker Hostel

Mountain Harbour B&B and Hiker Hostel

3.5 out of 5
Price was $727, price is now $553 per person
$553
per person
Nov 21 - Nov 25
found 5 hours ago
Roundtrip non-stop flight included
Syracuse (SYR) to Tri-Cities (TRI)
9.2/10 Wonderful! (112 reviews)
As always, it’s a pleasure to stay a bit at Miuntain Harbour. Friendly, restful, and the food is exceptional. Can’t visit Tennessee without (at least) one night here.

Reviewed on Aug 11, 2025

Hard Rock Hotel & Casino Bristol

Hard Rock Hotel & Casino Bristol

2.5 out of 5
Price was $908, price is now $735 per person
$735
per person
Nov 21 - Nov 25
found 5 hours ago
Roundtrip non-stop flight included
Syracuse (SYR) to Tri-Cities (TRI)
9.2/10 Wonderful! (217 reviews)
I have to be honest. My husband and I have been waiting for this hotel and casino to open for a very long time! Couldn't wait to see Billy Bob Thornton and the Boxmasters! They were fabulous! We wanted to LOVE this venue! However.....the smoking in the casino absolutely RUINED it for us! I realize there is a non-smoking casino option, but they shove it in the basement corner, with some less than stellar games, gaming tables that are never open, and no bar! Also, if you have to walk through the smoking section to get to it, doesn't it kind of defeat the purpose?? Come on Hard Rock. Keep your beautiful hotel and casino beautiful and stop the smoking! Put the smoking section downstairs! Let us walk to our hotel room without walking through that fog! And to the concert venue (which is non-smoking) It is pointless to have a huge smoking section directly in the middle of everything and force your non-smokers to deal with it. And to offer less than best quality gaming to your non-smokers.

Reviewed on Aug 24, 2025

Americourt Extended Stays

Americourt Extended Stays

2 out of 5
Price was $547, price is now $465 per person
$465
per person
Nov 21 - Nov 25
found 5 hours ago
Roundtrip non-stop flight included
Syracuse (SYR) to Tri-Cities (TRI)
4.2/10 (385 reviews)
Great location , cheap price.

Reviewed on May 9, 2025

The Bristol Hotel

The Bristol Hotel

4 out of 5
Price was $830, price is now $741 per person
$741
per person
Nov 21 - Nov 25
found 5 hours ago
Roundtrip non-stop flight included
Syracuse (SYR) to Tri-Cities (TRI)
9.8/10 Exceptional! (1,002 reviews)
Very clean. Friendly. And dog friendly

Reviewed on Aug 17, 2025

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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
$130 nightly
The price is $148 total per night from Sep 2 to Sep 3
$148 total
Sep 2 - Sep 3
Total with taxes and fees
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
$61 nightly
The price is $70 total per night from Sep 1 to Sep 2
$70 total
Sep 1 - Sep 2
Total with taxes and fees
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
$95 nightly
The price is $105 total per night from Sep 1 to Sep 2
$105 total
Sep 1 - Sep 2
Total with taxes and fees
Pine Mountain State Resort Park
See all 427 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.

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Frequently asked questions

How much does a Cumberland Gap vacation package cost?
Offering great value package deals from $430 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?
You can generally find lower prices and better availability in January, June and December. Take a look at our cheap Cumberland Gap vacation packages and you could score some excellent off-season deals.
How many days is enough for Cumberland Gap?
Generally, a handful of days is enough to go to the major sights during your Cumberland Gap vacation. But if you want to have more time to unwind 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.
Does Expedia offer Book Now, Pay Later Cumberland Gap vacation packages?
Your Cumberland Gap trip should be a relaxing escape from your busy life, not a reason for money worries. So to give you that extra flexibility, we've teamed up with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.

Explore a world of travel with Expedia

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.