A mountainous landscape with autumn foliage and a valley shrouded in mist.

Cumberland Gap Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Cumberland Gap vacation rentals

A covered outdoor deck with wooden flooring and metal chairs.

1. Peaceful & Private! Pet-friendly Williamsburg Home

Peaceful & Private! Pet-friendly Williamsburg Home
3.0 star property
Williamsburg
$279 nightly
The price is $307
Oct 13 - Oct 14
Total with taxes and fees
Peaceful & Private! Pet-friendly Williamsburg Home
A spacious living room with wooden beams, leather sofas, a wooden coffee table, and a mounted deer head.

2. Peaceful Mountain Cabin w/ Views in Williamsburg

Peaceful Mountain Cabin w/ Views in Williamsburg
2.0 star property
Williamsburg
2.0 out of 10, (1 review)
"The owners were very polite. The only issue I had was that the listing online did not say anything about it being fully solar powered with no electricity. We left in the middle of the night the first night because there was no power at all."
United States
Chandler
$310 nightly
The price is $341
Oct 7 - Oct 8
Total with taxes and fees
Peaceful Mountain Cabin w/ Views in Williamsburg
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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Top Cumberland Gap Hotel Reviews

Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro

10/10 Excellent
"I fractured my foot before I came on this vacation. When I drove up in front of the Inn, the lady at the registration desk saw that I was in a boot and on a walker. She just immediately gave us a mobility handicap room. I thought that was very thoughtful of her. The room was clean neat the breakfast was fabulous. I would stay here again next time I’m in this area."
Stephen 1-night trip
Posted 14 hours ago
Sleep Inn & Suites Middlesboro

Find out more about Cumberland Gap

Everything you need to know about Cumberland Gap vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cumberland Gap vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cumberland Gap vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cumberland Gap vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cumberland Gap. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Cumberland Gap in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $175 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cumberland Gap rentals

At Expedia, we put the best Cumberland Gap vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Cumberland Gap rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cumberland Gap vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cumberland Gap. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Frequently asked questions

Are there vacation rentals in Cumberland Gap?

Yes, there are vacation rentals close to the most popular points of interest in Cumberland Gap, or you can go with a secluded option if you're looking for relaxation. Cumberland Gap is known for its riverfront and mountain views. Make sure you have time to check out the restaurants while you're in the area.

What are some of the best vacation rentals that Cumberland Gap has to offer?

Brand New, Spacious 9 bedroom, 9 1/2 bath Waterfront house in Lakeside Estates: Visitors like this Cumberland Gap vacation home rental. It offers a patio, a hot tub, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 9 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What can I see and do in Cumberland Gap?

Explore the area and family-friendly sights such as New Tazewell Municipal Park, or get out into nature at a spot like The Pinnacle. Cumberland Gap National Historical Park and Lincoln Memorial University are a couple of places you'll find in the larger area.

What are vacation rentals like in Cumberland Gap?

Vacation rentals are private accommodations you can stay in for several days or longer in Cumberland Gap. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from public hotel elevators and busy concierge desks while still allowing you to travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for a small group gathering.