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Cumberland Holiday Rentals

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Holiday Rentals in Cumberland

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

10.0 out of 10, Exceptional, (2)
"Very cute house with everything you need"
Direct Access to Waterfall/Creek Trail of Leatherwood Off Road Park

Charming 2-bedroom house in Wise, Virginia

10.0 out of 10, Exceptional, (2)
"We had everything we needed and the neighborhood was quiet. Will definitely stay again! "
The price is AU$270
includes taxes & fees
28 July - 29 July
Charming 2-bedroom house in Wise, Virginia

Close to town, the college and a beautiful serene surrounding

9.6 out of 10, Exceptional, (50)
"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

Laptop-Friendly Appalachian Mountain Retreat!

10.0 out of 10, Exceptional, (9)
"Our family of 4 loved this house. Everything we needed was there and there was plenty of room for everyone."
Laptop-Friendly Appalachian Mountain Retreat!

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

10.0 out of 10, Exceptional, (2)
"Cabin was very nice and clean as described. There was plenty of outdoor activities but also clod to places to go out to eat. We had a fun and relaxing getaway. Would highly recommend this place. "
Cabin 1, Cozy Cottage with WiFi, Fireplace and Whirlpool Tub in Duffield, VA

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!

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

9.4 out of 10, Exceptional, (23)
"This was the perfect place for a long weekend getaway. The host communicated well and checked in via message to ensure everything was running smoothly. Very cute camper and surprisingly comfy beds - overall a wonderful experience. Thanks!"
The price is AU$384
includes taxes & fees
28 July - 29 July
Posh Mountain Camping w/ 120" Screen Theater ·Hot-Tub · Firepit · Hiking Trails

Welcome to The Mayor's Retreat! 4-bedroom house in Evarts KY. Book now

10.0 out of 10, Exceptional, (3)
"Great location very close to Black Mountain. Host was awesome"
Welcome to The Mayor's Retreat! 4-bedroom house in Evarts KY. Book now

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

10.0 out of 10, Exceptional, (1)
"beautiful slice of paradise!"
Spacious and Accessible 2 BR Cabin in Duffield, VA near Devil's Bathtub

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.

Handicapped Friendly House in the peaceful country side

10.0 out of 10, Exceptional, (25)
"Check in is easy and Nell is very responsive. This was my family's second time staying here and we will definitely stay again. "
Handicapped Friendly House in the peaceful country side

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

9.8 out of 10, Exceptional, (6)
"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, (7)
"Enjoyed the hot tub and outdoor TV. Looking forward to renting again."
The price is AU$439
includes taxes & fees
28 July - 29 July
Ramblin Rose 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)

Whitesburg Vacation Home w/ Screened Porch

9.6 out of 10, Exceptional, (7)
"We enjoyed our stay hope to come back next year"
Whitesburg Vacation Home w/ Screened Porch

Entire Home near Whitesburg

Entire Home near Whitesburg

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

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

10.0 out of 10, Exceptional, (12)
"Exceptional place with executional comfort with exceptional care to make your stay special. It was beautifully decorated and very welcoming for the winter holidays. "
The price is AU$211
includes taxes & fees
26 July - 27 July
Nottingham Turret Rm w Queen Bed, Near UVaWise & Main St, Private Detached Bath

360 Degree Mountain View

9.8 out of 10, Exceptional, (8)
"Family reunion great time! "
The price is AU$455
includes taxes & fees
3 Aug - 4 Aug
360 Degree Mountain View

Harlan, KY GuestHouse 300 Vacation/Weddings/Events (Cole Mansion)

10.0 out of 10, Exceptional, (1)
"Had a few issues but they were resolved."
Harlan, KY GuestHouse 300 Vacation/Weddings/Events (Cole Mansion)
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 Hotel Reviews

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?

Direct Access to Waterfall/Creek Trail of Leatherwood Off Road Park: This holiday home rental outside of Cumberland is located on a river, and has a patio, a garden and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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.