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Cumberland Holiday Rentals

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Holiday Rentals in Cumberland

Harlan, KY GuestHouse 300 Vacation/Weddings/Events (Cole Mansion)
10.0 out of 10, Exceptional, 1 review
"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
10.0 out of 10, Exceptional, 6 reviews
"My sister and I were visiting family nearby so we booked the Rambling Rose. It was such a fun and relaxing trip. The camper is so cute and much bigger than we expected. It's perfect for those who want to have all the fun of camping but still have the comforts of home!"
The price is NZ$483
includes taxes & fees
23 June - 24 June
Ramblin Rose Mtn Camping w/Theater * Hot-Tub * Fire-Pit
360 Degree Mountain View
9.8 out of 10, Exceptional, 6 reviews
"The property was very clean on the inside and the beds and bathrooms were abundant! The only true downside to the property is the parking and location to stores and restaurants, but if you are familiar with the area, like us, then you already know what to expect. We very much appreciated that there is a decent place to stay in that area of Kentucky!"
The price is NZ$618
includes taxes & fees
23 June - 24 June
360 Degree Mountain View
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Modern Appalachian Vacation Rental w/ River Access
10.0 out of 10, Exceptional, 5 reviews
"The driveway in is a little intimidating at first but it leads to a great private setting and a very comfortable cabin. The sounds of the creek are with you all the time creating a very relaxing atmosphere. The wildlife was fun to watch and the property is very easy to walk around in. Overall, it's a very pleasant place to get away and unplug for a while."
Modern Appalachian Vacation Rental w/ River Access
Posh Mountain Camping w/ 120" Screen Theater ·Hot-Tub · Firepit
9.8 out of 10, Exceptional, 14 reviews
"Hikes were amazing in the area."
The price is NZ$483
includes taxes & fees
26 June - 27 June
Posh Mountain Camping w/ 120" Screen Theater ·Hot-Tub · Firepit
1896 Victorian Farmhouse
10.0 out of 10, Exceptional, 6 reviews
"It was more than expected."
1896 Victorian Farmhouse
Handicapped Friendly House in the peaceful country side
10.0 out of 10, Exceptional, 18 reviews
"Working in the area, nice quite place to recoup for the next days adventure"
Handicapped Friendly House in the peaceful country side
Gated Mansion: Tennis Court, Movie Theater, Views, Pool, & More Near Bristol
Gated Mansion: Tennis Court, Movie Theater, Views, Pool, & More Near Bristol
Close to town, the college and a beautiful serene surrounding
9.8 out of 10, Exceptional, 41 reviews
"We were in the area to celebrate our 60th anniversary. We had moved away from Coeburn years ago but wanted to celebrate with the many relatives in the area."
Close to town, the college and a beautiful serene surrounding
Lux Mtn Camping with ·Theater ·Hot-Tub ·Fire Pit
10.0 out of 10, Exceptional, 4 reviews
"We couldn’t have asked for anything more except for more time to enjoy all the amenities."
The price is NZ$440
includes taxes & fees
23 June - 24 June
Lux Mtn Camping with ·Theater ·Hot-Tub ·Fire Pit
Whitesburg Vacation Home w/ Screened Porch
9.4 out of 10, Exceptional, 3 reviews
"I was so glad to find this property! We go to Whitesburg to visit family & need a place to stay. There aren’t any nice hotels in Whitesburg so this house was a blessing. It was a very nice house & large. Thank you!"
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 reviews
"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 NZ$286
includes taxes & fees
29 June - 30 June
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, 6 reviews
"This is very nice, clean and well stocked with everything you could image. If you forgot something it’s there! Beautiful home and rooms!"
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
10.0 out of 10, Exceptional, 8 reviews
"We enjoyed a variety of first-rate accommodations during our two-week trek down the Crooked Road. But none matched Nottingham Place … it’s beauty, comfort and remarkable hospitality shown by Ben and Kim. We’re already planning a return trip and the Nottingham is at the top of our list."
The price is NZ$268
includes taxes & fees
29 June - 30 June
Nottingham Turret Rm w Queen Bed, Near UVaWise & Main St, Private Detached Bath
The Holton #2 Brand New apartment near Lonesome Pine Hospital
10.0 out of 10, Exceptional, 1 review
"The place is exactly like what you see in the pix. We had everything we needed."
The Holton #2 Brand New apartment near Lonesome Pine Hospital
Harlan, KY Modern Private Guesthouse 302 Historic Downtown (Vela's Villas)
10.0 out of 10, Exceptional, 2 reviews
"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)
Whitesburg Vacation Home w/ Screened Porch
3.0 star property
10.0 out of 10, Exceptional, 1 review
"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
Brand New Apartment The Holton #2 in Big Stone Gap near Lonesome Pine Hospital
RV Camper on Private Campground
The price is NZ$153
includes taxes & fees
22 June - 23 June
RV Camper on Private Campground
Holton #1!
Holton #1!
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See all available properties in Cumberland
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.

Other types of properties in Cumberland you may be interested in

The Inn at Wise
3.0 star property
9.2 out of 10, Wonderful, 758 reviews
"Great spot - I stay here every time I come to Wise! "
The price is NZ$198
includes taxes & fees
23 June - 24 June
The Inn at Wise
Days Inn by Wyndham Norton
2.0 star property
6.8 out of 10, 277 reviews
"Great staff. Nice rooms"
The price is NZ$122
includes taxes & fees
21 July - 22 July
Days Inn by Wyndham Norton
Quality Inn & Suites
2.5 star property
9.4 out of 10, Exceptional, 369 reviews
"All around great experience with great service "
The price is NZ$213
includes taxes & fees
23 June - 24 June
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Cumberland holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Cumberland. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Cumberland. Seeing all the best attractions is bound to make you fall in love with Cumberland. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Cumberland short-term rentals, that won’t be hard to do.

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?

Harlan, KY GuestHouse 300 Vacation/Weddings/Events (Cole Mansion): This holiday home rental outside of Cumberland is located in the city centre, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a garden.

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.

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