Holiday Homes in Cumberland

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Find holiday rentals that suit your style

Apartment image
Apartments
Apartments
cabin image
Cabins
Cabins

Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Cumberland holiday homes

A porch with two Adirondack chairs and a small table, white siding, and a door with a glass panel.

1. Nan’s Porch - 2 Bedroom home with outdoor firepit

Nan’s Porch - 2 Bedroom home with outdoor firepit
Cumberland
The price is €271
includes taxes & fees
15 Nov - 16 Nov
Nan’s Porch - 2 Bedroom home with outdoor firepit
A covered porch with a doormat, a view of a backyard with a pool, and a wooden deck.

2. Dan’s Den - Two-bedroom home with hot tub, fire pit, and dog park

Dan’s Den - Two-bedroom home with hot tub, fire pit, and dog park
Cumberland
The price is €320
includes taxes & fees
14 Nov - 15 Nov
Dan’s Den - Two-bedroom home with hot tub, fire pit, and dog park
An outdoor patio with a table and benches, a wooden fence, and a door labeled "OUTHOUSE".

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

Bed and Biscuit Inn Pet friendly ! Near Kingdom come park & Pine mtn.
Partridge
9.8 out of 10, Exceptional, (16 reviews)
"Best stay we have had in the area. Wonderful place. Will stay here again!!!"
United States
Darren
The price is €132
includes taxes & fees
15 Nov - 16 Nov
Bed and Biscuit Inn Pet friendly ! Near Kingdom come park & Pine mtn.
A covered patio with a table and chairs, a ceiling fan, and potted plants.

4. Holler's End, at the "head of the holler" but just 4.5 miles from Whitesburg

Holler's End, at the "head of the holler" but just 4.5 miles from Whitesburg
whitesburg
10.0 out of 10, Exceptional, (5 reviews)
"Great place. Lotsa room & everything very nice clean. "
United States
Aaron G.
The price is €204
includes taxes & fees
25 Nov - 26 Nov
Holler's End, at the "head of the holler" but just 4.5 miles from Whitesburg
A covered porch with white columns, outdoor furniture, and potted plants.

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

Nottingham Turret Rm w Queen Bed, Near UVaWise & Main St, Private Detached Bath
Wise
10.0 out of 10, Exceptional, (14 reviews)
"Very comfortable stay! "
United States
Chasity F.
The price is €140
includes taxes & fees
14 Nov - 15 Nov
Nottingham Turret Rm w Queen Bed, Near UVaWise & Main St, Private Detached Bath
A deck with a round table and four chairs, surrounded by a white railing.

6. Charming 2-bedroom house in Wise, Virginia

Charming 2-bedroom house in Wise, Virginia
Wise
10.0 out of 10, Exceptional, (15 reviews)
"Such a beautiful place with so many special touches. We love being here and enjoying Wise County. The host creates a beautiful and comfortable space."
United States
Chasity F.
The price is €187
includes taxes & fees
22 Nov - 23 Nov
Charming 2-bedroom house in Wise, Virginia
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.
View all properties

Learn more about Cumberland

Hikers find solace on the trails of Kingdom Come State Park, where dramatic rock formations and mountain views await. Nearby Harlan County offers underground adventures at Portal 31 Mine Tour, showcasing the region's rich coal mining heritage.

See all hotels in Cumberland
A waterfall cascading over rocky terrain surrounded by dense forest.