Holiday rentals in Whitesburg

5 out of 5 average rating, 40 reviews

A porch area features two black chairs and a small wooden table, inviting relaxation outdoors. A decorative plant in a blue pot adds a touch of greenery, while the entrance to the guesthouse is adorned with a small diamond motif and an American flag.

Guest house in Blackey

An Appalachian Mountain Getaway. ATV friendly

Nestled in the mountains of Eastern Kentucky, this location offers stunning mountain views. It's ATV friendly, with secure and complimentary vehicle parking. A multitude of trails are available for riding, with walking paths on the property. Riding tours are also offered. The accommodation features a newly remodeled one full bed, a walk-in shower, and all the amenities, including a complete mini kitchen and a 32" TV. It's a peaceful and relaxing retreat after a day spent exploring the trails.

4.98 out of 5 average rating, 185 reviews

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

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!

4.92 out of 5 average rating, 161 reviews

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

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.

4.96 out of 5 average rating, 228 reviews

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

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

4.98 out of 5 average rating, 195 reviews

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

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

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.

4.97 out of 5 average rating, 574 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.

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.

4.99 out of 5 average rating, 83 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.

A well-maintained single-story home is depicted, featuring a red brick exterior and a welcoming front porch. A neatly trimmed lawn and two garden beds frame the entrance. Adjacent to the porch, a dark pickup truck is parked on a concrete driveway, providing easy access.

4.86 out of 5 average rating, 29 reviews

The Cozy Corner

This home is ideally located just minutes from downtown Whitesburg, within walking distance to Main Street and the Tanglewood bike and walking Trail. Recently remodeled, it features a fully stocked kitchen and dining area, as well as a spacious backyard. There is ample street and carport parking for up to 2 cars.

4.92 out of 5 average rating, 115 reviews

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

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.

The room features two queen size beds adorned with patterned bedding. A comfortable seating area with a chair and table is positioned near a window, allowing natural light to fill the space. Art pieces are displayed on the walls, enhancing the inviting decor.

4.99 out of 5 average rating, 152 reviews

‘The Junction Apartment’ Charming and spacious!

Newly remodeled, This space is the perfect spot for all of your traveling needs. It has all the comforts of home! A comfortable living space, cable tv, internet access, full kitchen stocked with all the necessities, a desk for a convenient work space, 2 queen size beds, full bath, large patio and ample parking.

4.91 out of 5 average rating, 100 reviews

A charming cabin exterior is presented, featuring rustic wooden siding and a dark metal roof. A spacious front porch is accessible by steps, flanked by sturdy wooden railings. Surrounding grassy areas are visible, contributing to the natural setting of the cabin.

Cabin in Leburn

Deer Run Cabin (1) near Mine Made Adventure Park

A cabin located on private property next to ATV Training Center at the Mine Made Adventure park in Knott Co, Ky. This is the perfect weekend getaway with access to over a 1,000 miles of ATV and UTV trails. You will be able to experience all the beauty located in the mountains of Eastern Kentucky.

A modern studio apartment is featured, showcasing a comfortable seating area with a light-colored sofa. A round coffee table sits centrally, with a television mounted on the wall. The sleeping area is visible, highlighting a spacious bed and soft, natural light from the window.

4.94 out of 5 average rating, 69 reviews

Law Office Studio

Kick back and relax in this calm, stylish studio apartment. Located on the first floor behind a law office. *We do not have control of the property around the building, we just have an easement of a pathway to the door*

Popular amenities for Whitesburg holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Whitesburg

The exterior of a cottage is displayed, featuring a covered porch with wooden railing and stairs leading to the entrance. Lush green plants and trees frame the front, while a gentle slope of the hillside is visible in the background.

4.94 out of 5 average rating, 158 reviews

The Blue Roof Cottage

5 out of 5 average rating, 12 reviews

Private room in Hazard

Farmhouse Queen Bedroom

A cozy seating area features a patterned sofa adorned with decorative pillows and a chair. Soft light emanates from a lamp on a side table. The adjacent bedroom showcases a spacious bed and a Roku TV mounted on the wall, complemented by natural light from a nearby window.

4.91 out of 5 average rating, 80 reviews

Main Street Studio

A spacious living area is presented with a sectional sofa facing a bright coffee table on a patterned area rug. A floral accent chair complements the modern decor. Large windows allow natural light to fill the room, enhancing the neutral color palette.

4.65 out of 5 average rating, 66 reviews

Whitesburg Vacation Home w/ Screened Porch

4.98 out of 5 average rating, 119 reviews

A spacious living area features a comfortable sectional sofa arranged around a round area rug. A dining table is positioned nearby, and a kitchenette with white appliances is visible in the background, providing a functional space for relaxation and dining.

Private room in Wise

Cozy Guest Suite in Historic Downtown Wise

5 out of 5 average rating, 33 reviews

The spacious bedroom features two queen beds adorned with vibrant red bedding and decorative pillows. Soft neutral walls create a calming atmosphere, while framed artwork adds visual interest. A bedside lamp provides additional lighting, enhancing the inviting feel of the room.

Flat in Pikeville

Convenient & Modern 2 Bed Apt Free Wi-Fi & Parking

5 out of 5 average rating, 12 reviews

The exterior of a charming single-family home features a large front porch with comfortable seating. The entrance is accessible by steps leading to a manicured lawn surrounded by greenery. A concrete pathway leads from the sidewalk to the front porch, highlighting the inviting nature of the property.

Home in Cumberland

Joe’s place (trailer parking available )