Holiday houses in Cumberland

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Cumberland

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

%{current} / %{total}1 / 1
Top Guest favourite
The exterior of a rural home is displayed, featuring a welcoming front porch with wooden railings and seating. Lush greenery from the surrounding trees provides a natural backdrop. A dark blue front door and decorative elements, such as potted plants, enhance the inviting appearance.
Home in Big Creek
4.97 out of 5 average rating, 120 reviews

Daniel Boone Forest-Easy Park-I75-Hal Rogers Pkwy

Nestled within the Daniel Boone National Forest, approximately 13 miles from the Clay County seat of Manchester, our newly built, veteran-owned, pet-friendly, rural getaway awaits you and your guests! With several amenities including a private hot tub, twin-size porch bed swing, Nintendo Switch Game System, and fire pit with seating, you’re sure to feel right at home. Enjoy the thousands of acres of nearby hunting land, ATV trails (famous Red Bird Crest Trail, 0.9 miles away) or just relaxing!

Guest favourite
A rustic cabin stands surrounded by lush greenery, featuring a wooden exterior and a sloping roof. A stone pathway leads to the front porch, which includes steps for easy access. A balcony overlooks the serene landscape, enhancing the cabin's charm.
Cabin in Sneedville
4.9 out of 5 average rating, 127 reviews

Rustic Retreat Cabin - Peace andTranquility

If you are looking for a peaceful place to relax and recharge then look no further. Rustic Retreat is a beautiful little cabin located in the majestic hills of Hancock Co. TN. This newly remodeled retreat is located about 2 1/2 miles from the town of Sneedville on Prospect Ridge. It provides all the basic amenities to make your stay as comfortable as possible. You can sit on the porch and enjoy the view, go for a walk or just relax inside, reading or watching TV. Join us, unplug and relax.

Top Guest favourite
Home in Dryden
4.99 out of 5 average rating, 112 reviews

Farm house with animals 10 minutes from Big Stone

Relax in our serene guest house situated atop a hill on a working farm on private country drive. Gorgeous 360 views of the surrounding mountains and pasture. Sip coffee on the front porch as the sun rises, and enjoy stunning sunsets from the back porch rockers! Cows, horses, sheep, donkey, deer closeby. Peaceful rural retreat with modern flare! Close to great dining and Trail of the Lonesome Pine outdoor drama in Big Stone Gap. Pickle balls and racquets provided for courts in Big Stone!

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, 111 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
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, 202 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!

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
4.98 out of 5 average rating, 167 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, 169 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.

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, 214 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.

Guest favourite
The rustic log cabin is framed by lush greenery, with a stone chimney and a welcoming porch decorated with seasonal accents. A gravel pathway leads to the entry, and an array of colorful flowers adds a touch of vibrancy to the exterior.
Cabin in Whitesburg
4.98 out of 5 average rating, 204 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, 616 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, 212 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 luxurious spa, 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
A cozy living area features a comfortable gray sofa with decorative cushions and a green armchair. A dark coffee table sits in front, complemented by a patterned area rug. Wall art and lamps add character, while soft lighting creates a welcoming ambiance.
Guesthouse in Whitesburg
4.98 out of 5 average rating, 213 reviews

The Potting Shed

This unique space is so charming you may never want to leave! Newly renovated with all the conveniences of home! A comfortable living space, fully stocked kitchen, free Wi-Fi and cable TV, beautiful outdoor patio space, outdoor grill and several items available for you to borrow for the perfect hike or picnic! It's the perfect spot for exploring Whitesburg and Letcher County. We know you will absolutely love your home away from home!

Popular amenities for Cumberland holiday rentals

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