Holiday Rentals in Cumberland Gap

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Our top choices for Cumberland Gap holiday rentals

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
Cumberland Gap
9.2 out of 10, Wonderful, (42)
"Great location. Easy walk to town and close to hiking areas. Highly recommend. "
United States
Linda O.
The price is €183
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Peaceful & Private! Pet-friendly Williamsburg Home

Peaceful & Private! Pet-friendly Williamsburg Home
3.0 star property
Williamsburg
The price is €261
includes taxes & fees
29 Dec - 30 Dec
Peaceful & Private! Pet-friendly Williamsburg Home

Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!

Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!
Tazewell
10.0 out of 10, Exceptional, (4)
"Everything was clean and felt like home.host was really nice and I will definitely be staying again."
United States
Nicholas H.
The price is €141
includes taxes & fees
5 Jan - 6 Jan 2026
Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!

Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina

Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
Speedwell
9.4 out of 10, Exceptional, (19)
"It was exceptional "
United States
Dennis W.
The price is €139
includes taxes & fees
30 Dec - 31 Dec
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina

One Bedroom Rustic Cabin

One Bedroom Rustic Cabin
2.0 star property
Speedwell
The price is €77
includes taxes & fees
29 Dec - 30 Dec
One Bedroom Rustic Cabin

Harrogate Home Mountain View’s Dog Friendly

Harrogate Home Mountain View’s Dog Friendly
Harrogate
10.0 out of 10, Exceptional, (22)
"Great location with friendly neighbors!"
United States
Evan C.
The price is €260
includes taxes & fees
30 Dec - 31 Dec
Harrogate Home Mountain View’s Dog Friendly

4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,

4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
Middlesboro
10.0 out of 10, Exceptional, (23)
"Very nice and extra clean great time"
United States
Johnny C.
The price is €203
includes taxes & fees
29 Dec - 30 Dec
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,

Modern 20’ Travel Trailer with bunks and a queen bed

Modern 20’ Travel Trailer with bunks and a queen bed
2.0 star property
Speedwell
The price is €108
includes taxes & fees
29 Dec - 30 Dec
Modern 20’ Travel Trailer with bunks and a queen bed

RV/Camper Sites. No Electric

RV/Camper Sites. No Electric
2.0 star property
Speedwell
The price is €61
includes taxes & fees
29 Dec - 30 Dec
RV/Camper Sites. No Electric

2-bedroom apartment in adorable Pineville with AC for relaxing stays

2-bedroom apartment in adorable Pineville with AC for relaxing stays
2.0 star property
Pineville
2-bedroom apartment in adorable Pineville with AC for relaxing stays

Serenity Villa: Luxurious Retreat with Hot Tub, Rooftop Deck & Mountain View's

Serenity Villa: Luxurious Retreat with Hot Tub, Rooftop Deck & Mountain View's
Sharps Chapel
10.0 out of 10, Exceptional, (5)
"This was definitely the most romantic VRBO we’ve stayed at!!! Very clean, and the view from all of the balconies was incredible!!! "
United States
Stan N.
The price is €254
includes taxes & fees
5 Jan - 6 Jan 2026
Serenity Villa: Luxurious Retreat with Hot Tub, Rooftop Deck & Mountain View's

Peaceful & Private! Pet-Friendly Williamsburg Home

Peaceful & Private! Pet-Friendly Williamsburg Home
2.0 star property
Williamsburg
The price is €261
includes taxes & fees
29 Dec - 30 Dec
Peaceful & Private! Pet-Friendly Williamsburg Home

Charming 3-bedroom house with WiFi, AC in Pineville Kentucky

Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
Pineville
10.0 out of 10, Exceptional, (2)
"We stayed here for a wedding weekend in Pineville, KY, and it was absolutely perfect from start to finish. The home was spotless, cozy, and had everything we could possibly need. The beds were so comfortable, and we instantly felt at home the moment we walked in.What truly set this stay apart was the host’s kindness and above-and-beyond hospitality. We got lost in the middle of the night trying to find the property, and the host stayed on the phone with us, patiently guiding us right to the...
United States
Samantha P.
The price is €258
includes taxes & fees
29 Dec - 30 Dec
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky

Tranquil Haven MTN Retreat, 3-bedroom, 2-bath, WIFI, AC in Beautiful Tazewell

Tranquil Haven MTN Retreat, 3-bedroom, 2-bath, WIFI, AC in Beautiful Tazewell
2.0 star property
Tazewell
10.0 out of 10, Exceptional, (7)
"Great place that is well stocked and close to amenities as well. Spacious house with an awesome porch with a view!"
United States
Brendan W.
The price is €383
includes taxes & fees
31 Dec - 1 Jan 2026
Tranquil Haven MTN Retreat, 3-bedroom, 2-bath, WIFI, AC in Beautiful Tazewell

The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!

The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!
Pineville
9.0 out of 10, Wonderful, (2)
"The home was just perfect for what we needed. Looking forward to seeing how it comes out when all construction is finished! Host was very responsive. Will stay again"
United States
Kami L.
The price is €220
includes taxes & fees
21 Jan - 22 Jan 2026
The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!

Charming 2-bedroom bungalow with AC, WiFi in pleasant Pineville

Charming 2-bedroom bungalow with AC, WiFi in pleasant Pineville
Pineville
10.0 out of 10, Exceptional, (1)
"Well cared for property with nice upgrades! Perfect for our stay, everything we needed, and accommodating. "
United States
Hope C.
The price is €192
includes taxes & fees
4 Jan - 5 Jan 2026
Charming 2-bedroom bungalow with AC, WiFi in pleasant Pineville

Waterfront Retreat, Sleeps 12・Fireplace・Grill・Dock

Waterfront Retreat, Sleeps 12・Fireplace・Grill・Dock
2.0 star property
Rock Harbor
The price is €416
includes taxes & fees
5 Jan - 6 Jan 2026
Waterfront Retreat, Sleeps 12・Fireplace・Grill・Dock

Norris Lake home w/boat slip at Sugar Hollow Marina, close to golf and winery

Norris Lake home w/boat slip at Sugar Hollow Marina, close to golf and winery
La Follette
9.2 out of 10, Wonderful, (17)
"Nice stay"
United States
Courtney A.
The price is €559
includes taxes & fees
28 Jan - 29 Jan 2026
Norris Lake home w/boat slip at Sugar Hollow Marina, close to golf and winery

Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.

Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
Middlesboro
9.2 out of 10, Wonderful, (5)
"We enjoyed our stay. "
United States
Emily S.
The price is €324
includes taxes & fees
29 Dec - 30 Dec
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.

Spacious Lakefront Home, Sleeps 8・Dock・Pool Table

Spacious Lakefront Home, Sleeps 8・Dock・Pool Table
2.0 star property
Sharps Chapel
The price is €486
includes taxes & fees
4 Jan - 5 Jan 2026
Spacious Lakefront Home, Sleeps 8・Dock・Pool Table
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

Find out more about Cumberland Gap

Everything you need to know about Cumberland Gap holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cumberland Gap holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Cumberland Gap holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cumberland Gap holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cumberland Gap holiday rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cumberland Gap rentals

At Expedia, we put the best Cumberland Gap holiday 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 holiday.

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. 

Frequently asked questions

Are there holiday rentals in Cumberland Gap?

Yes, there are holiday rentals close to the most popular sights in Cumberland Gap, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Cumberland Gap has to offer?

Norris Lake Home with Heated Saltwater Pool and Hot Tub in Deerfield: This holiday home rental outside of Cumberland Gap is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a patio and 1 hot tub.

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 wider area.

What are holiday rentals like in Cumberland Gap?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Cumberland Gap. Holiday rentals feature extras like WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a clean environment, holiday rentals can provide a sense of safety away from public hotel lifts and busy concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for family trips or small group gatherings.