Photo by Everett Scott

Cumberland Holiday Rentals

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Holiday Rentals in Cumberland

Our top choices for Cumberland holiday rentals

Cozy log cabin near Pennington Gap and Jonesville, VA known as "The Duck Pond"

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great cabin and beautiful location!!!"
Cozy log cabin near Pennington Gap and Jonesville, VA known as "The Duck Pond"

Charming 2-bedroom house in Wise, Virginia

10.0 out of 10, Exceptional, (5)
The price is AU$268
includes taxes & fees
15 Sept - 16 Sept
Charming 2-bedroom house in Wise, Virginia

Cabin 1, Cozy Cottage with WiFi, Fireplace and Whirlpool Tub in Duffield, VA

10.0 out of 10, Exceptional, (3)
"Cabin was very clean and well stocked and in a beautiful setting. We really enjoyed our stay. Thanks !"
Cabin 1, Cozy Cottage with WiFi, Fireplace and Whirlpool Tub in Duffield, VA

Spacious and Accessible 2 BR Cabin in Duffield, VA near Devil's Bathtub

9.0 out of 10, Wonderful, (2)
"Great spot to explore the area!!"
Spacious and Accessible 2 BR Cabin in Duffield, VA near Devil's Bathtub

Posh Mountain Camping w/ 120" Screen Theater ·Hot-Tub · Firepit · Hiking Trails

9.4 out of 10, Exceptional, (23)
"Definitely one of my favorite places I've ever stayed and I've been a lot of places. From the camper to the fire pit with wood included to the s'mores fixings to the hot tub to the theatre to the thoughtful pet friendly touches. I could have stayed forever and definitely hope to return sooner than later! "
The price is AU$389
includes taxes & fees
15 Sept - 16 Sept
Posh Mountain Camping w/ 120" Screen Theater ·Hot-Tub · Firepit · Hiking Trails

Nottingham Turret Rm w Queen Bed, Near UVaWise & Main St, Private Detached Bath

10.0 out of 10, Exceptional, (13)
"Very comfortable stay! "
The price is AU$217
includes taxes & fees
16 Sept - 17 Sept
Nottingham Turret Rm w Queen Bed, Near UVaWise & Main St, Private Detached Bath

Direct Access to Waterfall/Creek Trail of Leatherwood Off Road Park

10.0 out of 10, Exceptional, (4)
"Very cute house with everything you need"
Direct Access to Waterfall/Creek Trail of Leatherwood Off Road Park

4BR 2 bath house with full kitchen, living room, hot tub and game room.

10.0 out of 10, Exceptional, (2)
"Nice place great for rzr riding "
4BR 2 bath house with full kitchen, living room, hot tub and game room.

Bed and Biscuit Inn Pet friendly ! Near Kingdom come park & Pine mtn.

9.8 out of 10, Exceptional, (7)
"Perfect little place to hang with the pups and use as a base camp for lots of great hiking in the area. "
Bed and Biscuit Inn Pet friendly ! Near Kingdom come park & Pine mtn.

Ramblin Rose Mountain Camping with Theater, Hot-Tub, Fire-Pit & Hiking Trails

10.0 out of 10, Exceptional, (8)
"Enjoyed the hot tub and outdoor TV. Looking forward to renting again."
The price is AU$370
includes taxes & fees
15 Sept - 16 Sept
Ramblin Rose Mountain Camping with Theater, Hot-Tub, Fire-Pit & Hiking Trails

Luxe Mountain Camping with Theater, Hot Tub, Fire Pit & Hiking Trails

10.0 out of 10, Exceptional, (7)
"It is a great place for a little relaxation in the hot-tub and as an amazing romantic getaway! "
Luxe Mountain Camping with Theater, Hot Tub, Fire Pit & Hiking Trails

Harlan, KY Modern Private Guesthouse 302 Historic Downtown (Vela's Villas)

8.8 out of 10, Excellent, (3)
"We will rent this property again :)"
Harlan, KY Modern Private Guesthouse 302 Historic Downtown (Vela's Villas)

Charming 2-bedroom cabin in Duffield, VA. Near Devil's Bathtub & Natural Tunnel

9.8 out of 10, Exceptional, (8)
"The cabin exceeded expectations. The perfect Virginia stay in a beautiful forest. "
Charming 2-bedroom cabin in Duffield, VA. Near Devil's Bathtub & Natural Tunnel

Close to town, the college and a beautiful serene surrounding

9.6 out of 10, Exceptional, (53)
"The outside was not as clean and mowed as I expected , we complained about a blocked sink but no one responded . The bed was comfortable and I loved the size of the living room with its decor . "
Close to town, the college and a beautiful serene surrounding

Charming 1-bedroom house in welcoming Big Stone Gap Virginia!

10.0 out of 10, Exceptional, (2)
"This newly remodeled home was perfect for our family. There were four of us but there was room for two more to sleep. Everything was so clean! We loved the fact that the owner immediately responded when we had questions. The house is walking distance to the cute main street in Big Stone Gap and there are lots of beautiful hiking paths in the nearby mountains. We would definitely stay here again. "
Charming 1-bedroom house in welcoming Big Stone Gap Virginia!

Whitesburg Vacation Home w/ Screened Porch

3.0 star property
10.0 out of 10, Exceptional, (1)
"The property was clean and just as advertised. The owner was also very flexible in extending our check out time by a little bit since the checkout time was 10 and we had a funeral at 1, leaving us with 3 hours of downtime. We were all very appreciative and would leave a higher review if possible!"
Whitesburg Vacation Home w/ Screened Porch

Entire Home near Whitesburg

Entire Home near Whitesburg

360 Degree Mountain View

9.8 out of 10, Exceptional, (8)
"Very clean and comfortable. Everything we needed was there and available. "
The price is AU$454
includes taxes & fees
16 Sept - 17 Sept
360 Degree Mountain View

Tiny Treehouse Escape with Wi-Fi, Modern Amenities, BBQ Deck + Mountain Views

10.0 out of 10, Exceptional, (1)
"Although it rained the whole night we very much enjoyed our stay and would definitely stay again if we are ever back in Jonesville..We loved the rustic feel and simplistic, but adequate amenities.."
The price is AU$395
includes taxes & fees
15 Sept - 16 Sept
Tiny Treehouse Escape with Wi-Fi, Modern Amenities, BBQ Deck + Mountain Views

Pappy's Coal Miner's Cabin

10.0 out of 10, Exceptional, (1)
"Only problem I saw was no chlorine tablets in hot tub other than that perfect stay"
Pappy's Coal Miner's Cabin
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Cumberland Hotel Reviews

Find out more about Cumberland

Find out more about Cumberland

Everything you need to know about Cumberland 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 holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Cumberland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cumberland. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cumberland 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 holiday rentals we have selected for you start as low as AU$217 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Cumberland rentals

At Expedia, we put the best Cumberland 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 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 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. 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

Can I find a holiday rental in Cumberland?

Yes, there are holiday rentals close to the most popular sights in Cumberland, or you can select a more secluded option if you're looking for a relaxing stay. Cumberland is known for its parks.

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

Charming 2-bedroom house in Wise, Virginia: This holiday home rental outside of Cumberland offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What’s there to see and do in Cumberland?

While exploring the area, visit family-friendly sights like Rapid River Lodge & Water Park, or get outside and enjoy nature at Jefferson National Forest. Kingdom Come State Park and Black Mountain are a couple of places you'll find in the wider area.

What’s a holiday rental in Cumberland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cumberland. Holiday rentals offer amenities such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for small groups.