Cumberland Gap Vacations from $562

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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 Hotel

Americourt Hotel

2.5 out of 5
Price was $669, price is now $562 per person
$562
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Portland (PWM) to Tri-Cities (TRI)
6.6/10 (517 reviews)
Property clean. This Property is Old no frills. Clean and cheap. Vending machine, ice, coffee from give or take 6am till early afternoon. Pet friendly, quiet, safe, convenient area.

Reviewed on Nov 25, 2025

Hard Rock Hotel & Casino Bristol

Hard Rock Hotel & Casino Bristol

2.5 out of 5
Price was $1,073, price is now $905 per person
$905
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Portland (PWM) to Tri-Cities (TRI)
9.2/10 Wonderful! (262 reviews)
We really enjoyed ourselves at this property. Room was clean, bed was comfy. Casino was very lively with plenty of games. Overall we will definitely be back.

Reviewed on Dec 8, 2025

Home2 Suites by Hilton Johnson City, TN

Home2 Suites by Hilton Johnson City, TN

3 out of 5
Price was $846, price is now $752 per person
$752
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Portland (PWM) to Tri-Cities (TRI)
9.4/10 Exceptional! (271 reviews)
Clean room, friendly staff.

Reviewed on Dec 1, 2025

Comfort Suites Kingsport South

Comfort Suites Kingsport South

2.5 out of 5
Price was $752, price is now $673 per person
$673
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Portland (PWM) to Tri-Cities (TRI)
9/10 Wonderful! (955 reviews)
Stayed 3 nights, everything was great. Room was very clean, breakfast area was clean and well maintained. I would definitely stay here again.

Reviewed on Nov 18, 2025

Tru By Hilton West Bristol Tn

Tru By Hilton West Bristol Tn

2.5 out of 5
Price was $772, price is now $694 per person
$694
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Portland (PWM) to Tri-Cities (TRI)
8/10 Very Good! (5 reviews)
THis is a step down from a Hampton Inns, new timber construction where you can hear guests walking over your head, minimalist room arrangement, too close to interstate I81m (ditto Hampton Inns) next to car dealership and nothing else. Last choice.

Reviewed on Oct 22, 2025

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Cumberland Gap Hotel Deals

Cumberland Gap Inn

Cumberland Gap Inn

2.5 out of 5
630 Brooklyn Street Cumberland Gap TN
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $111 total per night from Dec 11 to Dec 12
$111 total
Dec 11 - Dec 12
Total with taxes and fees
8/10 Very Good! (583 reviews)
First floor room room perfect for us with our dog. Easy outside exit in back. Beside small creek. Very clean and comfortable bed. Will go back.

Reviewed on Oct 24, 2025

Cumberland Gap Inn
The Olde Mill Inn Bed & Breakfast

The Olde Mill Inn Bed & Breakfast

2.5 out of 5
603 Pennlyn Avenue Cumberland Gap TN
9.6/10 Exceptional! (177 reviews)
Very clean room, fantastic pieces inside with lots of history and a magnificent breakfast!!

Reviewed on Nov 21, 2025

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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
$74 nightly
The price is $85 total per night from Dec 28 to Dec 29
$85 total
Dec 28 - Dec 29
Total with taxes and fees
7.2/10 Good! (1,000 reviews)
We did not visit the pool,but it looked nice. Staff was very friendly and helpful. Especially the front desk people. Our housekeeper was very helpful. Also,very convenient to the highway.

Reviewed on Nov 16, 2025

Days Inn by Wyndham Jellico - Tennessee State Line
See all 475 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

How much does a Cumberland Gap vacation package cost?
Offering great value package deals from $562 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.

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