Cumberland Gap Vacation Packages
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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.
Top Cumberland Gap Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Motel 6 Kingsport, TN
Price was CA $695, price is now CA $626 per person
CA $626
per person
Apr 2 - Apr 6
found 12 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Tri-Cities (TRI)
8/10 Very Good! (1,002 reviews)
The only place that my son and I stay at in Kingsport :) The staff is wonderful and the rooms are always welcoming.
Reviewed on Dec 28, 2025
Comfort Suites Kingsport South
Price was CA $880, price is now CA $789 per person
CA $789
per person
Apr 2 - Apr 6
found 12 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Tri-Cities (TRI)
9/10 Wonderful! (955 reviews)
Great room, service, and breakfast. Thank you each and everyone for a fantastic stay. I will be back!
Reviewed on Jan 22, 2026
Quality Inn Downtown
Price was CA $856, price is now CA $769 per person
CA $769
per person
Apr 2 - Apr 6
found 12 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Tri-Cities (TRI)
7.4/10 Good! (542 reviews)
Everything was in order, right off the highway but quiet. Good beds, decent breakfast.
Reviewed on Jan 6, 2026
Super 8 by Wyndham Kingsport
Price was CA $1,019, price is now CA $921 per person
CA $921
per person
Apr 2 - Apr 6
found 12 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Tri-Cities (TRI)
6.8/10 (400 reviews)
Place is quiet. They don't tolerate bs so it's a whole lot better than what's around. Staff is always nice
Reviewed on Feb 6, 2026
Quality Inn Johnson City I-26 exit 17
Price was CA $744, price is now CA $678 per person
CA $678
per person
Apr 2 - Apr 6
found 12 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Tri-Cities (TRI)
7.4/10 Good! (256 reviews)
Room was clean and convenient to I-26. Front desk folks were very friendly.
Reviewed on Feb 5, 2026
Cumberland Gap Hotel Deals
The Olde Mill Inn Bed & Breakfast
603 Pennlyn Avenue Cumberland Gap TN
The price is CA $174 per night from Feb 28 to Mar 1
CA $174
CA $198 total
Feb 28 - Mar 1
includes taxes & fees
9.6/10 Exceptional! (179 reviews)
The staff was excellent. They are wonderful people. They made sure everything was perfect. We enjoyed having breakfast with the other guests. They addressed any allergy concerns and tailored your breakfast for all. I would recommend this bed and breakfast it is the best one we have ever stayed ...
Reviewed on Jan 18, 2026
Sleep Inn & Suites Middlesboro
1260 N, 12th Street Middlesboro KY
Fully refundable
The price is CA $132 per night from Feb 16 to Feb 17
CA $132
CA $148 total
Feb 16 - Feb 17
includes taxes & fees
9/10 Wonderful! (820 reviews)
Belinda at the desk is amazing She made our stay excellent , she made us feel like we were old friends . We will be staying here on each visit .
Reviewed on Jan 24, 2026
Pine Mountain State Resort Park
1050 State Park Road Pineville KY
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (680 reviews)
Cabin was clean and well furnished
Reviewed on Jan 21, 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.
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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.
