Holiday rentals in Cumberland

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Top-rated holiday rentals in Cumberland

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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, 102 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!

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
A modern tiny home is nestled among greenery, featuring a spacious porch supported by sleek black pillars. The exterior showcases a combination of wood and stone accents, while outdoor seating with a small table invites relaxation. Large windows provide ample natural light.
Tiny home in Surgoinsville
4.96 out of 5 average rating, 182 reviews

Eloheh

Amazing tiny home situated on 23 very private acres, conveniently located just off main highway. Newly constructed in 2023, this modern studio offers an enormous amount of amenities including full kitchen, dual showers, hot tub, outdoor TV, high speed WiFi, multiple TV viewing services, outdoor dining set, grill, multiple fire features, mountain views, lots of room for short hikes or nature walks, area with sunset views only a short distance from the house, only 1.5 miles to riverfront park.

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!

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.

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, 208 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 exterior of the cottage features a facade of Kentucky River rock complemented by red brick accents. A gray metal roof extends over a small porch area with two wooden benches. Flower pots with white blooms sit on either side of the entrance.
Cottage in Whitesburg
4.95 out of 5 average rating, 232 reviews

The Stone Studio

A historic two-room studio cottage built from Kentucky River rock. Entire cottage rented for your privacy. Recently renovated with the modern conveniences of a kitchenette, outdoor smoking area, Wi-Fi, RokuTV, and blackout curtains. High ceilings create a bright and spacious feel. Conveniently located close to downtown. Off street parking by your front door. Walk to Main Street, Appalshop, and Kentucky Mist Distillery as well as many other small businesses and restaurants

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
4.98 out of 5 average rating, 200 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, 600 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, 205 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 wooden staircase leads to a door framed by greenery. The steps, crafted from natural wood, provide access to a green and blue exterior. A small seating area with two chairs is visible to the side, inviting relaxation outdoors.
Flat in Whitesburg
4.99 out of 5 average rating, 100 reviews

Dandelion Bungalow

This special place is close to downtown Whitesburg and right across from the entrance of Tanglewood Trail. It is within walking distance of Kentucky Mist, a few local restaurants, a recreational center, the farmer’s market, and Cane Kitchen. We are located at the foot of the scenic Pine Mountain and a short drive to hiking trails, overlooks, and other attractions.

Top guest favourite
A view of a bustling downtown street is presented, featuring a mix of vehicles, storefronts, and local signage. The street is lined with trees and mountains can be seen in the distance under a clear blue sky. American flags add a touch of local charm.
Flat in Big Stone Gap
4.92 out of 5 average rating, 119 reviews

Perfect location above Big Cherry Brewing

Situated in the heart of Big Stone Gap. You will be within walking distance of all the entertainment, museums, shops, history, and food fare. Right downstairs is Big Cherry Brewing which features amazing food, entertainment, and even a brunch and gourmet coffee menu in additon to a huge selection of craft beers.

Popular amenities for Cumberland holiday rentals

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