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Compare 27 Vacation Homes in Cumberland with updated reviews, rates, and availability.

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

9.6 out of 10, Exceptional, (5)
"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.

Laptop-Friendly Appalachian Mountain Retreat!

10.0 out of 10, Exceptional, (7)
"Great visit - House was convenient, clean, and had everything we needed for our visit. Area is great place to visit especially at this time of year. Definitely would stay here again."
Laptop-Friendly Appalachian Mountain Retreat!

Entire Home near Whitesburg

Entire Home near Whitesburg

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

8.8 out of 10, Excellent, (3)
"Plenty of space for a family. Adequate furnishings in kitchen to fix meals. I found parking confusing, as the streets are one-way."
Harlan, KY Modern Private Guesthouse 302 Historic Downtown (Vela's Villas)

360 Degree Mountain View

9.8 out of 10, Exceptional, (8)
"Thank you we had an amazing weekend and everything was perfect ! Will most definitely book again"
The price is AED 551
AED 1,389 total
includes taxes & fees
1 Jul - 2 Jul
360 Degree Mountain View

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

Handicapped Friendly House in the peaceful country side

10.0 out of 10, Exceptional, (25)
"If you want peace and quiet, this is the place to vacation to!"
Handicapped Friendly House in the peaceful country side

Historic Property in Hyden KY

10.0 out of 10, Exceptional, (1)
"Had the most peaceful relaxing stay in the mountains. If you can, open the windows and listen to the creek and sleep well."
Historic Property in Hyden KY

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

10.0 out of 10, Exceptional, (1)
"Very cute house with everything you need"
Direct Access to Waterfall/Creek Trail of Leatherwood Off Road Park

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)

Close to town, the college and a beautiful serene surrounding

9.8 out of 10, Exceptional, (47)
"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, (1)
"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!

1896 Victorian Farmhouse Farm Stay

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 Farm Stay

Modern Appalachian Vacation Rental w/ River Access

9.8 out of 10, Exceptional, (8)
"We had a very beautiful and restful stay, thank you!"
Modern Appalachian Vacation Rental w/ River Access

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 404
AED 531 total
includes taxes & fees
9 Jun - 10 Jun
Nottingham Turret Rm w Queen Bed, Near UVaWise & Main St, Private Detached Bath

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 459
AED 593 total
includes taxes & fees
12 Jun - 13 Jun
Victorian Spa EnSuite @ Nottingham PL, King Bed, Jacuzzi Near UVa-Wise & Main St

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

10.0 out of 10, Exceptional, (7)
"The place was absolutely beautiful, from the outside of the house to the inside. We had a bedroom, living room and a bathroom. The place was extremely clean, comfortable and quiet. The owners were great to work with in communication and are extremely friendly. This is a must stay place when you are visiting the area. We will be booking here again and will look to book here every time we visit the area"
Nottingham Place in Wise, King Bedrm, Private Living Rm, Near UVa-Wise & Main St

Gorgeous Historic Haven downtown (Rare find)

Gorgeous Historic Haven downtown (Rare find)

Perfect location above Big Cherry Brewing

Perfect location above Big Cherry Brewing

Unreal Bungalow downtown (Perfect location)

Unreal Bungalow downtown (Perfect location)
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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