Photo by Everett Scott

Search Vacation Homes in Cumberland

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation
Bed and Biscuit Inn Pet friendly ! Near Kingdom come park & Pine mtn.
8.0 out of 10, Very good, (1)
"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.
Handicapped Friendly House in the peaceful country side
10.0 out of 10, Exceptional, (21)
"This place was absolutely beautiful, loved the decor with the antiques, and really enjoyed the outside deck and carport, beautiful views, and Nell and her husband is awesome. I will no doubt stay there again! "
Handicapped Friendly House in the peaceful country side
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
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)
360 Degree Mountain View
9.8 out of 10, Exceptional, (7)
"Family reunion great time! "
The price is HK$855
HK$2,538 total
includes taxes & fees
12 Nov - 13 Nov
360 Degree Mountain View
Modern Appalachian Vacation Rental w/ River Access
9.8 out of 10, Exceptional, (8)
"We had a great time during our stay. It was very quiet and relaxing. The house is modern and clean. It had everything we needed. Woke up to wild life in the yard. Enjoyed our time at the river."
Modern Appalachian Vacation Rental w/ River Access
Posh Mountain Camping w/ 120" Screen Theater ·Hot-Tub · Firepit
9.2 out of 10, Wonderful, (17)
"Everything was great and relaxing until that night when the breaker was thrown. But the host immediately tried to fix the issue. Responded to us quickly even can out to help us and offered other accommodations ! Will book again because the location is so relaxing and the beds were comfortable "
The price is HK$972
HK$1,852 total
includes taxes & fees
11 Nov - 12 Nov
Posh Mountain Camping w/ 120" Screen Theater ·Hot-Tub · Firepit
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
Gated Mansion: Tennis Court, Movie Theater, Views, Pool, & free vineyard tours !
Gated Mansion: Tennis Court, Movie Theater, Views, Pool, & free vineyard tours !
Whitesburg Vacation Home w/ Screened Porch
9.6 out of 10, Exceptional, (5)
"Booked for a coworker who was working in Jenkins"
Whitesburg Vacation Home w/ Screened Porch
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."
Victorian Spa EnSuite @ Nottingham PL, King Bed, Jacuzzi Near UVa-Wise & Main St
Nottingham Turret Rm w Queen Bed, Near UVaWise & Main St, Private Detached Bath
10.0 out of 10, Exceptional, (9)
"This house is gorgeous! I loved the historic features and it’s decorated beautifully! These hits think of everything you might need and have so many personal touches. I have loved staying here and I’ll definitely be back. Thank you so much! "
The price is HK$1,166
HK$1,479 total
includes taxes & fees
11 Nov - 12 Nov
Nottingham Turret Rm w Queen Bed, Near UVaWise & Main St, Private Detached Bath
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. "
Nottingham Place in Wise, King Bedrm, Private Living Rm, Near UVa-Wise & Main St
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!
10.0 out of 10, Exceptional, (4)
"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!
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
Perfect Vacation home
Unreal Bungalow downtown (Perfect location)
Unreal Bungalow downtown (Perfect location)
Gorgeous Historic Haven downtown (Rare find)
Gorgeous Historic Haven downtown (Rare find)
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.
Don't see what you're looking for?
See all available properties in Cumberland
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Cumberland

Handicapped Friendly House in the peaceful country side
10.0 out of 10, Exceptional, (21)
"This place was absolutely beautiful, loved the decor with the antiques, and really enjoyed the outside deck and carport, beautiful views, and Nell and her husband is awesome. I will no doubt stay there again! "
Handicapped Friendly House in the peaceful country side
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
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)
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.