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

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.

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
County home

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
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
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
Miscellaneous

360 Degree Mountain View

9.8 out of 10, Exceptional, (7)
"Family reunion great time! "
The price is SAR 338
SAR 1,130 total
includes taxes & fees
22 Dec - 23 Dec
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
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, (18)
"My mom, aunt, best friend and I came for our birthdays for a long weekend. We're from Michigan so the drive up the mountain threw us off a bit at first but we made it and it was worth it. Gorgeous, peaceful and so awesome. Watching Schittz Creek in the hot tub was the best! "
The price is SAR 469
SAR 895 total
includes taxes & fees
26 Nov - 27 Nov
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, (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 !
Exterior

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
Living Room | Free WiFi | Smart TV W/ Cable + Netflix

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
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."
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 432
SAR 564 total
includes taxes & fees
3 Dec - 4 Dec
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. "
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, (5)
"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)
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
Unreal Bungalow downtown (Perfect location)
Property grounds

Unreal Bungalow downtown (Perfect location)

Unreal Bungalow downtown (Perfect location)
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

9.6 out of 10, Exceptional, (5)
"Booked for a coworker who was working in Jenkins"
Whitesburg Vacation Home w/ Screened Porch
Handicapped Friendly House in the peaceful country side
County home

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
Ramblin Rose Mtn Camping w/Theater * Hot-Tub * Fire-Pit
Property grounds

Ramblin Rose Mtn Camping w/Theater * Hot-Tub * Fire-Pit

10.0 out of 10, Exceptional, (7)
"What a wonderful property! We loved the privacy of our site and the outdoor area was so fun and relaxing for my partner and I! The hot tub was a hit for him and provided much pain relief and I loved having the ability to cook on the griddle/grill combo! We met Wes on our way out and had a wonderful talk about the area and local culture- he was very knowledgeable and friendly. We both hope to be back for another visit soon! "
The price is SAR 469
SAR 895 total
includes taxes & fees
26 Nov - 27 Nov
Ramblin Rose Mtn Camping w/Theater * Hot-Tub * Fire-Pit
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.