Search Villas in Cumberland Gap

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Find holiday rentals that suit your style

Apartment image
Apartments
Apartments
Cottage image
Cottages
Cottages

Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Learn more about Cumberland Gap

Hike the historic mountain pass where Daniel Boone blazed the Wilderness Road at Cumberland Gap National Historical Park. Rangers at the visitor centre offer guided tours of Gap Cave and Hensley Settlement, where you'll discover pioneer life.

See all hotels in Cumberland Gap
A mountainous landscape with a valley shrouded in clouds, rocky outcrops, and autumn-colored foliage.

Top reviews in Cumberland Gap

A Sleep Inn & Suites building with a covered entrance, stone pillars, and a clear blue sky.
Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro
Middlesboro

10/10 Excellent

Clean and great service
United Kingdom
Lar
Reviewed May 16, 2025
Sleep Inn & Suites Middlesboro