Cumberland Gap Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$134 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
Top hotels in Cumberland Gap
The Olde Mill Inn Bed & Breakfast
603 Pennlyn Avenue Cumberland Gap TN
The price is S$175 per night from 12 Feb to 13 Feb
S$175
12 Feb - 13 Feb
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 18 Jan, 2026
Sleep Inn & Suites Middlesboro
1260 N, 12th Street Middlesboro KY
Fully refundable
The price is S$137 per night from 16 Feb to 17 Feb
S$137
16 Feb - 17 Feb
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 24 Jan, 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 21 Jan, 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.
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
