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Holiday houses in Cumberland

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Top-rated holiday rentals in Cumberland

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A mountain log cabin features a spacious wrap-around deck and large windows showcasing scenic views. Set against a lush green lawn, the cabin's wood exterior is complemented by natural stone accents. Surrounding trees add to the serene atmosphere.
Cabin in Jonesville
4.94 out of 5 average rating, 110 reviews

H&B Cabin and Farm at Wilder Bent

Beautiful mountain log cabin with modern amenities located on the Powell River. Our home has a spacious kitchen, large dinning table for family meals, and a gorgeous stone fireplace made from stone found on the property. The lower level is very private and is perfect for parents, in-laws, or teens. This is a peaceful get-a-way with plenty of fishing, hiking, and kayaking. Just a few minutes from Jonesville, VA, Hwy. 58 and tourist attractions in driving distance. Your home away from home!

Top Guest favourite
The front view of the ranch-style brick home reveals a neatly trimmed lawn and a metal roof. Windows frame the entrance, which features a decorative glass panel door. In the background, rolling hills display a serene rural landscape.
Farm stay in Jonesville
4.97 out of 5 average rating, 109 reviews

Maw's House Handicapped Friendly House in country

This two bedroom ranch style brick home located on a working farm will delight you with its view and open country spaces. Enjoy seeing wildlife such as deer, turkey, and squirrels on the property. This home is handicapped friendly. All entrances have a ramp, the bathroom commodes are raised, the shower in the main bath is handicapped, and there are grab bars in the necessary places. Equipment available for the handicapped are: Wheelchair, Lift Chair, Rollator, commode chair, walker.

Top Guest favourite
A welcoming entrance to the Mountain Escape Cottage is depicted, featuring a wooden sign displaying the name prominently. Colorful flower pots filled with vibrant blooms frame the entrance, while the cottage stands amidst a backdrop of trees under a clear blue sky.
Cottage in Lynch
4.98 out of 5 average rating, 195 reviews

Cozy 3-BR 2-bath cottage near highest point in KY

Nestled in the heart of Lynch, KY, surrounded by comforting mountains, sets the Mountain Escape Cottage. Less than 1 mile from Portal 31, you can dive deep into the rich history of this tiny coal town. Within minutes you can drive to ATV parks, the highest point in KY, and many other mountainous adventures. Grab some coffee at the old cafe turned coffee shop, and visit the KY Coal Museum just 5 minutes away in Benham, KY. You and your family will leave here with beautiful mountain memories!

Top Guest favourite
A misty landscape of rolling green mountains is visible, with dense trees lining the lower slopes. Low-lying clouds drift at the mountain peaks, creating a serene atmosphere. The scene highlights the natural beauty of the surrounding area.
Apartment in Gate City
4.99 out of 5 average rating, 163 reviews

Small Town Summer Nights, Hiking Concerts Relaxing

Housed in a restored office building along the Clinch Mountain, Roberts Mill Suites offers a fully renovated loft with the comforts of home. Skylight in the living room bathes the space in natural light and provides relaxing sounds during a rainstorm The Suites are near Southwest VA treasures Natural Tunnel State Park, Devil's Bathtub and the Carter Family Fold. Minutes away from Kingsport TN and Bristol TN/VA, we offer accommodation to wedding guests, race fans, festival goers and family.

Guest favourite
The exterior of the home showcases a well-maintained landscape, featuring a variety of colorful flowers arranged in a stone-bordered garden. Steps lead to an inviting entrance with large windows and a decorative stone chimney, surrounded by lush greenery.
Home in Lynch
4.92 out of 5 average rating, 167 reviews

Tranquility in the Mountains - House

Peaceful getaway offers relaxation & adventure in the KY mountains. Short drive to VA & TN. Large home has 4 bedrooms - 2 w/ private bath & 2 that share a double-vanity bath. Open living/dining area and kitchen. Nearby is a 7-hole golf course and swimming pool (available Memorial Day - Labor Day), hiking, and tourist attractions such as Portal 31 and the KY Coalmine Museum, as well as Kingdom Come State Park. Plenty of parking; can accommodate trailers & RVs. RV park is a 45-minute drive.

Guest favourite
The exterior of a quaint country cottage is shown, featuring a red metal roof and multiple large windows. A wooden fence lines the front, complementing the surrounding greenery and neatly maintained garden beds. The entrance is framed by a simple gate, creating a welcoming appearance.
Cottage in Wise
4.75 out of 5 average rating, 140 reviews

Verna’s Place Country Cottage Peaceful Retreat

Unwind at Verna’s Place, a quaint country cottage nestled in the mountains of Southwest Virginia. This home, located in Wise, Virginia is a little over 4 miles from the campus of UVA-Wise and less than 2 miles from the local winery. Enjoy the serene mountain setting by relaxing on the patio or enjoy all the dining, shopping and outdoor activity options located just minutes away. Bigger is not always better and this unique country cottage is a perfect getaway for travelers of all types.

Top Guest favourite
A charming white house is softly illuminated at night, showcasing its inviting exterior. Tall trees stand in the background against a deep blue sky, framing the peaceful rural setting.
Farm stay in Dryden
4.96 out of 5 average rating, 206 reviews

Wolfe-Gilbert House 1890 Victorian & farm

Great mountain views, ATV Trails, State and National parks, hiking, underground mine tour, all-in-a-day trips. You’ll love my place because of the comfy beds, the high ceilings, the views, wide open spaces, peace. My place is good for couples, big groups, and furry friends, let us know your needs. Located less than 5 miles to Spearhead Trail's Stone Mountain trailhead and only 30 minutes to Mountain View Trail. Two couples fit nicely in the 1st level 2 bedrooms for a quaint getaway.

Top Guest favourite
The exterior of the chalet showcases a charming two-story structure with a distinctive red door. The landscaped yard features various plants and shrubs, bordered by a wooden fence, with a gravel pathway leading to the entrance. Lush greenery surrounds the property, emphasizing its natural setting.
Chalet in Kingsport
4.97 out of 5 average rating, 595 reviews

The Bearfoot Chalet Kingsport, TN

Our Mountain Chalet is the Perfect GETAWAY. Best location to stay in our ENTIRE Area. We are in the city limits of Kingsport, 3 miles from downtown. A DOG MUST BE PRE-APPROVED and there will be an additional pet fee. I do not charge a cleaning fee as long as guest leave place clean as found. Charter cable TV and WIFI access provided. Also located on our 6-acre estate is another BNB rental the "BEARFOOT RETREAT", a 3BR house should a larger group want to stay close together.

Guest favourite
An aerial view of a rustic log cabin framed by grassy terrain. The cabin features a metal roof and is surrounded by landscaped gardens. Outdoor seating is visible on the porch, enhancing the cabin's natural appeal against the backdrop of the Appalachian mountains.
Cabin in Whitesburg
4.97 out of 5 average rating, 199 reviews

BROWN’S ELK CABIN

Brown’s elk cabin is an Authentic, rustic, log cabin. Located in the heart of the beautiful Appalachian mountains, overlooking the KY river, Only a short drive to Pine Mtn hiking trails, Bad Branch Falls, Little Shepherd Trail, Kingdom Come State Park, Raven Rock golf course, and only twenty minutes from the Va. state line. Perfect getaway for relaxing with family and friends, sitting by the fire pit, or exploring the areas natural beauty. Located 3 miles from Whitesburg

Top Guest favourite
The cottage is a single-story building with a white exterior and a black roof. A decorative star is featured above the front window. A gravel driveway leads to a garage on the left, while a small porch with steps extends towards a well-maintained lawn with potted plants.
Home in Whitesburg
4.97 out of 5 average rating, 592 reviews

Cowan Creek Cottage

Cowan Creek Cottage is close to the Cowan Community Center and only 5½ miles outside the city limits of Whitesburg. The cottage is located at the foothills of Pine Mountain. You’ll love the cottage and enjoy the feel of having your own little home in the mountains. Enjoy a clean and comfortable home away from home while visiting friends and family and enjoying our community. Cowan Creek Cottage is good for couples, solo adventurers, business travelers, and families.

Top Guest favourite
An aerial view captures the unique repurposed silo with a circular design and a red tin roof. Surrounding greenery enhances the setting, while a hot tub and patio area with dining furniture are visible. Neatly arranged landscaping features small trees and decorative stones.
Farm stay in Sneedville
4.98 out of 5 average rating, 204 reviews

Red Bin

This memorable place is anything but ordinary. This repurposed Silo is located on a working farm. Featuring stunning craftsmanship and lots of relaxing amenities for up to two guest. The property includes stunning mountain views, hiking trails, a small creek for fishing, a hot tub, fire pit, and patio. AND, if you love the fall, the leaves can be spectacular here! The best is you do not have to fight the crowds in Smoky Mountain tourist traps!

Top Guest favourite
The exterior of Elk Creek Cottage is showcased, featuring a wooden facade surrounded by trees in autumn hues. A gravel driveway leads to the steps, and a spacious porch is visible with seating areas under an overhang, inviting guests to enjoy the natural surroundings.
Cottage in Bell County
4.99 out of 5 average rating, 350 reviews

Scenic 1 BR Cabin w/ Hiking to Hensley Settlement

“Elk Creek Cottage” borders Cumberland Gap National Historical Park property--the pathway to the west, trailblazed by Daniel Boone himself! Stay and hike to Hensley Settlement or Shillalah Creek Falls, or relax with a cup of coffee on the porch surrounded by nature. Only a scenic twenty-minute drive to Middlesboro or Pineville, KY separates you from the "city." Come enjoy the peace and quiet that Elk Creek Cottage has to offer.

Popular amenities for Cumberland holiday rentals

  1. Airbnb
  2. United States
  3. Kentucky
  4. Harlan County
  5. Cumberland