Visit Cumberland Gap: 2026 Travel Guide for Cumberland Gap, Tennessee

The Olde Mill Inn Bed & Breakfast

603 Pennlyn Avenue Cumberland Gap TN

Stay at this B&B in Cumberland Gap. Enjoy free breakfast, free parking, and conference space. Our guests praise the breakfast in our reviews. Popular attractions ...

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Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Cumberland Gap TN

$181 nightly

$203 total

Nov 19 - Nov 20

Total with taxes and fees

Stay at this cottage in Cumberland Gap. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions The Pinnacle and Cumberland Gap National Historical ...

9.4/10 Exceptional! (52 reviews)

"This is my fourth stay at this property. We love the Cumberland Gap area. We will definitely be returning and specifically to this lovely house. The location is ideal. The hosts communication is great. Can’t say enough good things about our stay here."

Reviewed on Oct 6, 2026

Pine Mountain State Resort Park

1050 State Park Road Pineville KY

$99 nightly

$109 total

Nov 3 - Nov 4

Total with taxes and fees

Book a stay at this golf hotel in Pineville. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...

9/10 Wonderful! (778 reviews)

"Beautiful location. Great value for excellent lodging and food."

Reviewed on Oct 30, 2026

See all 469 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.

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Cumberland Gap TN

Stay at this cottage in Cumberland Gap. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions The Pinnacle and Cumberland Gap National Historical ...

9.4/10 Exceptional! (52 reviews)

"This is my fourth stay at this property. We love the Cumberland Gap area. We will definitely be returning and specifically to this lovely house. The location is ideal. The hosts communication is great. Can’t say enough good things about our stay here."

Reviewed on Oct 6, 2026

Break Away - NEW Lakefront Modern Farmhouse 6BR-Outdoor Bar and Kitchen

LaFollette TN

Stay at this vacation home in La Follette. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Sugar Hollow Marina and Fork Bend are located ...

9.4/10 Exceptional! (48 reviews)

"House was gorgeous everything was clean and the host was very responsive with questions . Will be back again!"

Reviewed on Sep 7, 2026

Serene cabin with dock/swim platform in charming Speedwell

Speedwell TN

Stay at this cabin in Speedwell. Enjoy free WiFi, an in-room coffeemaker, and in-room fireplaces. Popular attractions Kincaid Historical Monument and Chuck Swan ...

See all 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.

Frequently asked questions

When is the best time to visit Cumberland Gap?

The best time to visit Cumberland Gap is from May through September. For travelers seeking fewer crowds and better value, the quieter months from November through February are a good bet, offering a cooler season to explore the area.

Can I book a refundable hotel in Cumberland Gap?

Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Cumberland Gap by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.

Why book a trip to Cumberland Gap with Expedia?

Expedia makes it easier to plan your Cumberland Gap trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.

Should I stay in a hotel or vacation rental in Cumberland Gap?

The best choice depends on your travel style. Hotels in Cumberland Gap can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.

How can I manage my Cumberland Gap trip on Expedia?

Once you've booked your Cumberland Gap trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.

What if I need help during my Cumberland Gap trip?

Expedia offers customer support before, during, and after your Cumberland Gap trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.

How can Expedia help me plan my first trip to Cumberland Gap?

If it's your first trip to Cumberland Gap, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.

How can I save on my Cumberland Gap hotel booking with Expedia?

Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Cumberland Gap hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.