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Compare 21 Vacation Homes in Cumberland with updated reviews, rates, and availability.

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)
360 Degree Mountain View
360 Degree Mountain View
9.8 out of 10, Exceptional, (7)
"Family reunion great time! "
The price is SAR 338
SAR 1,129 total
includes taxes & fees
26 Sep - 27 Sep
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, (7)
"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
Amp up your camping experience at our posh site featuring loads of amenities!
Posh Mountain Camping w/ 120" Screen Theater ·Hot-Tub · Firepit
9.4 out of 10, Exceptional, (16)
"We had a short but enjoyable stay. The place was clean and comfortable. Look forward to coming back."
The price is SAR 495
SAR 927 total
includes taxes & fees
24 Sep - 25 Sep
Posh Mountain Camping w/ 120" Screen Theater ·Hot-Tub · Firepit
1896 Victorian Farmhouse
Queen room main floor
1896 Victorian Farmhouse
10.0 out of 10, Exceptional, (8)
"Very happy with our stay. Listing was exactly as advertised. Karen was always available and helpful. Would highly recommend. Doug"
1896 Victorian Farmhouse
Handicapped Friendly House in the peaceful country side
County home
Handicapped Friendly House in the peaceful country side
10.0 out of 10, Exceptional, (19)
"This country home exceeded our expectations. It was very nice and had every amenity plus. Exceptional for younger ones as well as older or handicapped guests. Very peaceful location. The host was very attentive in providing directions and information leading up to our trip. I would highly recommend."
Handicapped Friendly House in the peaceful country side
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 !
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, (45)
"This stay was our 3rd visit to the property. We enjoy the location it is very quiet and convenient to area shops. "
Close to town, the college and a beautiful serene surrounding
Whitesburg Vacation Home w/ Screened Porch
Living Room | Free WiFi | Smart TV W/ Cable + Netflix
Whitesburg Vacation Home w/ Screened Porch
9.6 out of 10, Exceptional, (4)
"We enjoyed our stay hope to come back next year"
Whitesburg Vacation Home w/ Screened Porch
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 SAR 488
SAR 626 total
includes taxes & fees
24 Sep - 25 Sep
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
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, (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 SAR 450
SAR 585 total
includes taxes & fees
24 Sep - 25 Sep
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
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 SAR 525
SAR 668 total
includes taxes & fees
24 Sep - 25 Sep
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)
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, (3)
"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!
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.
Bed and Biscuit Inn Pet friendly ! Near Kingdom come park & Pine mtn.
Harlan, Ky Modern Private Guesthouse 304 Historic Downtown (Vela's Villas)
Exterior
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
Unreal Bungalow downtown (Perfect location)
Property grounds
Unreal Bungalow downtown (Perfect location)
Unreal Bungalow downtown (Perfect location)
Gorgeous Historic Haven downtown (Rare find)
Private kitchen
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
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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

Posh Mountain Camping w/ 120" Screen Theater ·Hot-Tub · Firepit
Amp up your camping experience at our posh site featuring loads of amenities!
Posh Mountain Camping w/ 120" Screen Theater ·Hot-Tub · Firepit
9.4 out of 10, Exceptional, (16)
"We had a short but enjoyable stay. The place was clean and comfortable. Look forward to coming back."
The price is SAR 495
SAR 927 total
includes taxes & fees
24 Sep - 25 Sep
Posh Mountain Camping w/ 120" Screen Theater ·Hot-Tub · Firepit
Handicapped Friendly House in the peaceful country side
County home
Handicapped Friendly House in the peaceful country side
10.0 out of 10, Exceptional, (19)
"This country home exceeded our expectations. It was very nice and had every amenity plus. Exceptional for younger ones as well as older or handicapped guests. Very peaceful location. The host was very attentive in providing directions and information leading up to our trip. I would highly recommend."
Handicapped Friendly House in the peaceful country side
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)
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.