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Check prices for these dates

Next weekend
14 Feb - 16 Feb
In two weeks
21 Feb - 23 Feb
In one month
7 Mar - 9 Mar
In two months
4 Apr - 6 Apr

Compare 22 Vacation Homes in Cumberland with updated reviews, rates, and availability.

Whitesburg Vacation Home w/ Screened Porch
Living Room | Free WiFi | Smart TV W/ Cable + Netflix

Whitesburg Vacation Home w/ Screened Porch

9.8 out of 10, Exceptional, (6)
"We came in to town for Thanksgiving. We generally stay with family but wanted our own place this time around. The pictures were spot on. It is a large home and has plenty of space to spread out if needed. The beds were cozy. We spent our evenings watching tv in the living room with the fireplace on. Pretty close to everything. Quiet little neighborhood."
Whitesburg Vacation Home w/ Screened Porch
Harlan, KY GuestHouse 300 Vacation/Weddings/Events (Cole Mansion)
Exterior

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)
Posh Mountain Camping w/ 120" Screen Theater ·Hot-Tub · Firepit · Hiking Trails
Amp up your camping experience at our posh site featuring loads of amenities!

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

9.4 out of 10, Exceptional, (19)
"Tom’s place was an overflow spot for a thanksgiving guest for whom we had no extra room. It was convenient, well maintained and very clean. Tom was quick to respond to all communication. We’ll book with him again."
The price is AED 459
AED 859 total
includes taxes & fees
7 Feb - 8 Feb
Posh Mountain Camping w/ 120" Screen Theater ·Hot-Tub · Firepit · Hiking Trails
360 Degree Mountain View
Miscellaneous

360 Degree Mountain View

9.8 out of 10, Exceptional, (7)
"Family reunion great time! "
The price is AED 331
AED 1,105 total
includes taxes & fees
13 Feb - 14 Feb
360 Degree Mountain View
Modern Appalachian Vacation Rental w/ River Access
Pennington Gap Vacation Rental | 1BR | 1BA | Stairs Required | 1,191 Sq Ft

Modern Appalachian Vacation Rental w/ River Access

9.8 out of 10, Exceptional, (8)
"Well maintained and beautifully perfect property and cabin. Private and quiet. My heart was sad when my stay was over. I will definitely be a return guest. Honest hosts. "
Modern Appalachian Vacation Rental w/ River Access
Close to town, the college and a beautiful serene surrounding
Golf

Close to town, the college and a beautiful serene surrounding

9.8 out of 10, Exceptional, (46)
"Very quiet location. Large house with plenty of room for several people. Close to downtown Wise."
Close to town, the college and a beautiful serene surrounding
Gated Mansion: Tennis Court, Movie Theater, Views, Pool, & free vineyard tours !
Exterior

Gated Mansion: Tennis Court, Movie Theater, Views, Pool, & free vineyard tours !

Gated Mansion: Tennis Court, Movie Theater, Views, Pool, & free vineyard tours !
Harlan, KY Modern Private Guesthouse 302 Historic Downtown (Vela's Villas)
Exterior

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

10.0 out of 10, Exceptional, (2)
"I was very pleased with the hospitality, having a wash room to use, and great kitchen, too. Could relax a little watching streaming channels, too."
Harlan, KY Modern Private Guesthouse 302 Historic Downtown (Vela's Villas)
Laptop-Friendly Appalachian Mountain Retreat!
Norton Vacation Rental | 3BR | 2BA | Step-Free Access Via Ramp | 1,629 Sq Ft

Laptop-Friendly Appalachian Mountain Retreat!

10.0 out of 10, Exceptional, (6)
"This property was immaculate. Very clean and lots of space for a whole family. Owner was very responsive when we had any questions. Will definitely stay there again, if the need arises."
Laptop-Friendly Appalachian Mountain Retreat!
Bed and Biscuit Inn Pet friendly ! Near Kingdom come park & Pine mtn.
Exterior

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

9.6 out of 10, Exceptional, (4)
"Even being dog friendly this property was kept very clean, the beds were comfortable and the home was very spacious! "
Bed and Biscuit Inn Pet friendly ! Near Kingdom come park & Pine mtn.
1896 Victorian Farmhouse
Queen room main floor

1896 Victorian Farmhouse

10.0 out of 10, Exceptional, (9)
"We enjoyed our stay at the farmhouse. Close enough to Pennington Gap for groceries and restaurants. "
1896 Victorian Farmhouse
Nottingham Turret Rm w Queen Bed, Near UVaWise & Main St, Private Detached Bath
Lodging Is Part Of Your Trip - Make It Memorable

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

10.0 out of 10, Exceptional, (10)
"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 AED 331
AED 450 total
includes taxes & fees
7 Feb - 8 Feb
Nottingham Turret Rm w Queen Bed, Near UVaWise & Main St, Private Detached Bath
Handicapped Friendly House in the peaceful country side
County home

Handicapped Friendly House in the peaceful country side

10.0 out of 10, Exceptional, (22)
"Very impressed, the house was very clean, we loved how it was decorated. The property was in a quite area but not isolated, the town was about 15 minutes out should we decide to go. All instructions concerning the location was easy to follow. The view was beautiful and would definitely recommend this rental and would be pleased to use it again."
Handicapped Friendly House in the peaceful country side
Nottingham Place in Wise, King Bedrm, Private Living Rm, Near UVa-Wise & Main St
King Heavenly Bed, Two Full Length Windows and Ceiling Fan

Nottingham Place in Wise, King Bedrm, Private Living Rm, Near UVa-Wise & Main St

10.0 out of 10, Exceptional, (7)
"This was the 3rd time my son and I stayed at Nottingham Place, everything was wonderful and we met one of the owner's, Kim, who was so nice and we had a wonderful chat. We finally got to enjoy sitting on the porch and the weather was perfect. "
The price is AED 367
AED 491 total
includes taxes & fees
7 Feb - 8 Feb
Nottingham Place in Wise, King Bedrm, Private Living Rm, Near UVa-Wise & Main St
Victorian Spa EnSuite @ Nottingham PL, King Bed, Jacuzzi Near UVa-Wise & Main St
Room

Victorian Spa EnSuite @ Nottingham PL, King Bed, Jacuzzi Near UVa-Wise & Main St

10.0 out of 10, Exceptional, (12)
"My son and I stayed at Nottingham Place for the second year and it was wonderful. We plan staying an extra day next year."
The price is AED 367
AED 491 total
includes taxes & fees
3 Mar - 4 Mar
Victorian Spa EnSuite @ Nottingham PL, King Bed, Jacuzzi Near UVa-Wise & Main St
Charming 1-bedroom house in welcoming Big Stone Gap Virginia!
Living area

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

Charming 1-bedroom house in welcoming Big Stone Gap Virginia!
Harlan, Ky Modern Private Guesthouse 304 Historic Downtown (Vela's Villas)
Exterior detail

Harlan, Ky Modern Private Guesthouse 304 Historic Downtown (Vela's Villas)

10.0 out of 10, Exceptional, (1)
"We loved our stay at Vela’s Villa! We had a family gathering and it was wonderful for us to all be together we had a family reunion and it was such a great stay! thanks so much"
Harlan, Ky Modern Private Guesthouse 304 Historic Downtown (Vela's Villas)
Perfect Vacation home
Room

Perfect Vacation home

Perfect Vacation home
Gorgeous Historic Haven downtown (Rare find)
Game room

Gorgeous Historic Haven downtown (Rare find)

Gorgeous Historic Haven downtown (Rare find)
Perfect location above Big Cherry Brewing
Living area

Perfect location above Big Cherry Brewing

Perfect location above Big Cherry Brewing
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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Other property types in Cumberland

Whitesburg Vacation Home w/ Screened Porch
Living Room | Free WiFi | Smart TV W/ Cable + Netflix

Whitesburg Vacation Home w/ Screened Porch

9.8 out of 10, Exceptional, (6)
"We came in to town for Thanksgiving. We generally stay with family but wanted our own place this time around. The pictures were spot on. It is a large home and has plenty of space to spread out if needed. The beds were cozy. We spent our evenings watching tv in the living room with the fireplace on. Pretty close to everything. Quiet little neighborhood."
Whitesburg Vacation Home w/ Screened Porch
4BR 2 bath house with full kitchen, living room, hot tub and game room.
Exterior

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

10.0 out of 10, Exceptional, (1)
"Nice place great for rzr riding "
4BR 2 bath house with full kitchen, living room, hot tub and game room.
Beautiful Loft in the Woods
Room

Beautiful Loft in the Woods

The price is AED 364
AED 721 total
includes taxes & fees
7 Feb - 8 Feb
Beautiful Loft in the Woods
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.