Photo by Everett Scott

Cumberland Holiday Rentals

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Holiday Rentals in Cumberland

Handicapped Friendly House in the peaceful country side
Golf
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
Fridge, microwave, oven, stovetop
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)
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)
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)
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 HK$972
HK$1,826 total
includes taxes & fees
10 Nov - 11 Nov
Ramblin Rose Mtn Camping w/Theater * Hot-Tub * Fire-Pit
360 Degree Mountain View
Miscellaneous
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
TV, fireplace
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
Bed and Biscuit Inn Pet friendly ! Near Kingdom come park & Pine mtn.
Property grounds
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.
Posh Mountain Camping w/ 120" Screen Theater ·Hot-Tub · Firepit
Pool
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$1,826 total
includes taxes & fees
10 Nov - 11 Nov
Posh Mountain Camping w/ 120" Screen Theater ·Hot-Tub · Firepit
1896 Victorian Farmhouse
Exterior
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 !
Smart TV, fireplace, video games, ping pong
Gated Mansion: Tennis Court, Movie Theater, Views, Pool, & free vineyard tours !
Gated Mansion: Tennis Court, Movie Theater, Views, Pool, & free vineyard tours !
Lux Mtn Camping with ·Theater ·Hot-Tub ·Fire Pit
Terrace/patio
Lux Mtn Camping with ·Theater ·Hot-Tub ·Fire Pit
10.0 out of 10, Exceptional, (5)
"It is a great place for a little relaxation in the hot-tub and as an amazing romantic getaway! "
The price is HK$770
HK$1,604 total
includes taxes & fees
6 Nov - 7 Nov
Lux Mtn Camping with ·Theater ·Hot-Tub ·Fire Pit
Whitesburg Vacation Home w/ Screened Porch
Fridge, microwave, stovetop, dishwasher
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
Terrace/patio
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 Place in Wise, King Bedrm, Private Living Rm, Near UVa-Wise & Main St
Exterior
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
Nottingham Turret Rm w Queen Bed, Near UVaWise & Main St, Private Detached Bath
Terrace/patio
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
Whitesburg Vacation Home w/ Screened Porch
Private kitchen
Whitesburg Vacation Home w/ Screened Porch
3.0 star property
10.0 out of 10, Exceptional, (1)
"The property was clean and just as advertised. The owner was also very flexible in extending our check out time by a little bit since the checkout time was 10 and we had a funeral at 1, leaving us with 3 hours of downtime. We were all very appreciative and would leave a higher review if possible!"
Whitesburg Vacation Home w/ Screened Porch
Brand New Apartment The Holton #2 in Big Stone Gap near Lonesome Pine Hospital
Private kitchen
Brand New Apartment The Holton #2 in Big Stone Gap near Lonesome Pine Hospital
Brand New Apartment The Holton #2 in Big Stone Gap near Lonesome Pine Hospital
3BR, 1 Bath Cabin with hot tub, full kitchen, and living room.
3 bedrooms, bed sheets
3BR, 1 Bath Cabin with hot tub, full kitchen, and living room.
3BR, 1 Bath Cabin with hot tub, full kitchen, and living room.
Secluded Cabin with a mountain view, hot tub, full kitchen, and living room.
Private kitchen
Secluded Cabin with a mountain view, hot tub, full kitchen, and living room.
10.0 out of 10, Exceptional, (1)
"We can’t wait to return. Everything was great."
Secluded Cabin with a mountain view, hot tub, full kitchen, and living room.
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 types of properties in Cumberland you may be interested in

The Inn at Wise
Exterior
The Inn at Wise
3.0 star property
9.4 out of 10, Exceptional, (835)
"The staff was amazing, the check in was quick and easy, and the room was perfect! Loved it here."
The price is HK$800
HK$891 total
includes taxes & fees
24 Nov - 25 Nov
The Inn at Wise
Rodeway Inn
Exterior
Rodeway Inn
2.0 star property
5.8 out of 10, (186)
"Gentleman at check in was very friendly and helpful. "
The price is HK$346
HK$392 total
includes taxes & fees
17 Nov - 18 Nov
Rodeway Inn
Quality Inn & Suites
Lobby
Quality Inn & Suites
2.5 star property
9.4 out of 10, Exceptional, (403)
"Very nice, staff was great, late check in was simple."
The price is HK$676
HK$746 total
includes taxes & fees
24 Nov - 25 Nov
Quality Inn & Suites
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.

Frequently asked questions

Can I find a holiday rental in Cumberland?

Yes, there are holiday rentals close to the most popular sights in Cumberland, or you can select a more secluded option if you're looking for a relaxing stay. Cumberland is known for its parks.

What are some of the best holiday rentals that Cumberland has to offer?

Handicapped Friendly House in the peaceful country side: This holiday home rental outside of Cumberland is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You can relax into your holiday with a private garden and a selection of games.

What’s there to see and do in Cumberland?

Kingdom Come State Park and Jefferson National Forest are a couple of lovely local spots to get outside and enjoy nature. Black Mountain and Black Mountain Offroad Adventure Area - Putney Trailhead are a couple of places you'll find in the wider area.

What’s a holiday rental in Cumberland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cumberland. Holiday rentals offer amenities such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for small groups.