Cumberland Gap Vacation Packages 2025/2026

Top Cumberland Gap hotels deals

The Olde Mill Inn Bed & Breakfast

603 Pennlyn Avenue, Cumberland Gap, TN

$145 nightly

$165 total

Nov 7 - Nov 8

Total with taxes and fees

This bed & breakfast doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace and wedding services are also provided.

Breakfast included

Parking included

Pine Mountain State Resort Park

1050 State Park Road, Pineville, KY

Free Cancellation

Reserve now, pay when you stay

$102 nightly

$113 total

Oct 27 - Oct 28

Total with taxes and fees

A golf course and an outdoor pool are featured at this smoke-free hotel. Enjoy a meal from the restaurant and perks like free self parking and free WiFi. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and concierge services.

Pool

Pet friendly

Sleep Inn & Suites

1260 N, 12th Street, Middlesboro, KY

Free Cancellation

Reserve now, pay when you stay

$99 nightly

$109 total

Nov 2 - Nov 3

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. There's a gym on site, and laundry facilities and free newspapers are also offered.

Breakfast included

Pet friendly

Holiday Inn Express Middlesboro by IHG

1252 N 12th St, Middlesboro, KY

Free Cancellation

$121 nightly

$133 total

Oct 12 - Oct 13

Total with taxes and fees

This hotel features an outdoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Pool

Breakfast included

Days Inn by Wyndham Jellico - Tennessee State Line

1417 5th Street, Jellico, TN

Free Cancellation

Reserve now, pay when you stay

$63 nightly

$72 total

Nov 3 - Nov 4

Total with taxes and fees

A full-service spa and an outdoor pool are featured at this smoke-free hotel. Business travelers can take advantage of the free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like on-the-go breakfast and free self parking.

Pool

Hot Tub

Econo Lodge Middlesboro

1623 Cumberland Avenue, Middlesboro, KY

Free Cancellation

Reserve now, pay when you stay

$85 nightly

$93 total

Oct 9 - Oct 10

Total with taxes and fees

A restaurant and a seasonal outdoor pool are featured at this motel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. The front desk is staffed around-the-clock and laundry facilities are on offer.

Pool

Breakfast included

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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.

Frequently asked questions

How much are vacation packages to Cumberland Gap?

Exciting adventures await you in Cumberland Gap, with Travelocity vacation packages starting from as low as . Providing both flights and hotels, these awesome deals make it really easy to discover all corners of the world.

How long should my Cumberland Gap vacation be?

If you need some guidance, most visitors spend around 2 nights vacationing in Cumberland Gap. But to discover the true spirit of this place, stay a few extra nights. You'll be able to tick off more attractions and really immerse yourself in the local culture.

Where can I get the best vacation package deals for Cumberland Gap?

Your dream vacation can be booked through Travelocity. With access to 400 airline partners and a whopping 1,000,000 hotels all over the world, selecting the ultimate Cumberland Gap package deal couldn't be easier.

Why should I purchase my Cumberland Gap vacation bundle via Travelocity?

With our Price Match Guarantee, we'll match any cheaper price you find. Add on our 24/7 customer support and top-quality service and your dream vacation is closer than ever before.

Will I save money on my Cumberland Gap car rental if I combine it with a hotel or flight?

With a Cumberland Gap vacation package, you can bundle your flight, car and hotel bookings and save a tidy sum. If you want to explore the best of this awesome city, why not start with Dollywood? This well-known sight is 55 mi from Cumberland Gap. With your own set of wheels, you'll be there soon enough.

Which airport is best for Cumberland Gap?

McGhee Tyson Airport (TYS), the major terminal in Cumberland Gap, is where you'll step off the plane. It's situated 60 mi south of the center of town.

Where should I stay when visiting Cumberland Gap?

The Cumberland Gap Inn is popular with many visitors. Book now to avoid missing out.