Family-friendly holiday rentals in Williamson

5 out of 5 average rating, 39 reviews

A single-story cabin with a welcoming front porch is illuminated by soft lighting. Colorful adirondack chairs are arranged along the porch, overlooking a gravel area. The structure features air conditioning units on each side, with surrounding trees in the background.

Cabin in Matewan

Sully's Cabin 2

Sully's Cabin 2 is built and furnished as a small home. Designed for couples, small families, or friends who want a smaller space but don't want to sacrifice luxury with their stay. Come off the trails and in 2 minutes you are back at your luxury cabin that offers the amenities of a full home. Fix meals in the fully stocked kitchen, or Blackstone Griddle, then relax on the front porch, or back patio by the fire pit, or just watch some TV. Max 4 guests, rent both cabins if you need added space.

4.94 out of 5 average rating, 124 reviews

The kitchen features a spacious island with four cushioned stools, modern pendant lighting, and a distinctive SMEG fridge. Clean countertops offer ample prep space, while stylish green tile backsplashes add a chic touch. The area is well-lit and flows seamlessly into the living space.

Apartment in Pikeville

Walk to dinner, UPIKE, hospital•3 Lux Bed• Balcony

Upstairs-The Eccentric Privy is the best of the best worlds. Retro, glam & quirky! You’ll obsess over the thought put into each room & even get some inspiration. Extra amenities include… Outdoor deck Quartz Countertops Luxury tile SMEG fridge Smart thermostat Bathroom Bluetooth speaker USB outlet in each room Soft close doors & drawers in kitchen & bathroom 550 TC cotton bed sheets and pillow covers Allergy defense, antimocrobial pillow protectors Tankless water heater for endless hot water

4.98 out of 5 average rating, 111 reviews

The exterior of the chalet features a two-story structure surrounded by lush greenery. A covered porch extends from the second level, and a staircase leads down to the landscaped yard. Pathways and railings create a welcoming access to the home.

Treehouse in Williamson

The Red Dog Chalet Couples Retreat w/ Hot Tub

Trailer access pull-thru private parking area with a beautiful lighted walking bridge that leads you to the chalet. A beautiful getaway with a spiral staircase leading you to the 2nd story covered porch with a wraparound walking deck. Large firepit area with dried fire wood. Large 12ft by 12ft hammock beside fire pit area. Two person copper tub; private outdoor shower; hot tub and large bed swing. Loft bedroom. Free WIFI. Park Series charcoal grill outside. Buffalo Mt trailhead 1/2 mile.

Tiny home in Forest Hills

A cozy living area includes a neutral-colored sofa with turquoise accent pillows and a soft area rug. Natural light enters through two windows with floral valances, illuminating the space. A small dining table with white chairs is visible in the background, enhancing comfort and functionality.

4.71 out of 5 average rating, 24 reviews

Cozy Creek Side Tiny Home - Walk to Distillery

Little Cottage offers a comfortable space for a quick visit or a lingering stay to explore everything in the community from riding the Hatfield-McCoy Trails, fishing the Tug River, hiking to the West Virginia swing, or some peace and quiet in a safe and friendly neighborhood. Conveniently located near shopping, restaurants and just a few miles from a trailhead. Plan a visit to Pauley Hollow Distillery less than a half a mile from Little Cottage for real moonshine and Kentucky bourbon!

4.96 out of 5 average rating, 124 reviews

A spacious living area features a comfortable brown leather sofa and a circular chair. A 58" TV is mounted on the wall, accompanied by a wooden entertainment unit. Natural light filters through sheer curtains, and decorative artwork is displayed on the walls.

Home in Prestonsburg

The Shotgun House

Enjoy your stay at the Shotgun house located in the heart of Prestonsburg within walking distance to a popular restaurant and downtown shopping. This cozy house offers a 58" TV and playstation in the living and also a 50" TV in the bedroom. Relax outside on a covered porch and enjoy the occasional local live music. Located close to the Prestonsburg Passage Trail, Mountain Arts Center, Middle Creek National Battlefield, Pikeville Exp Center and a short drive to the Red River Gorge.

4.98 out of 5 average rating, 132 reviews

An aerial view of a ranch-style house with wood siding, surrounded by a large yard and featuring an in-ground pool. The property includes manicured landscaping and a private setting against a hillside, showcasing ample outdoor space for relaxation and activities.

Home in McCarr

God's Country

Property is a ranch style house with wood siding, nestled against a hillside with a private setting. This property offers a large yard with a in-ground pool as well as a large front porch. There are two patio areas in the back with a built in grill station and a fire-pit to enjoy on those cool evenings. The house boasts six bedrooms, open concept living room, kitchen, and dining room area with gas fireplace, and large family room.Please enter the correct number of guest

5 out of 5 average rating, 36 reviews

The cottage's exterior is illuminated by warm lighting, showcasing a covered front porch with steps leading up to the blue door. The surrounding area features grassy landscaping, and the evening sky adds a serene backdrop.

Cottage in Williamson

A cozy 2 bedroom cottage

The Mountain Laurel House is a cottage that can comfortably accommodate 6 guests. Tucked in the Heart of the Appalachian Mountains, our cottage appeals to both adventurous ATV riders & couples looking for a relaxing getaway. Guests can enjoy the beautiful mountain views from the covered front porch, or they can sit by a fire in the yard. We are located 1/2 mile from Buffalo Mountain trailhead, which means no trailering necessary. Ample parking is provided.

5 out of 5 average rating, 32 reviews

A cozy living area features warm wooden walls and a gray sofa, complemented by decorative pillows. A blue accent chair adds a pop of color, while a large plant brings a touch of nature indoors. Light streams in from a skylight above.

Cabin in Pikeville

Inspiration Station

Inspiration Station at Harvey's Hideaway Haven is designed to uplift your spirit and ignite your inner drive. You will be immersed in nature, surrounded by the beauty of the wilderness. While this offers a peaceful escape, please be aware that you may encounter local wildlife, including bugs, bees, and other creatures that share this natural setting. Located just 9 miles from Pikeville Medical Center, Upike and The Appalachian Wireless arena!

4.93 out of 5 average rating, 172 reviews

A cabin exterior is illuminated at night, showcasing a wooden porch with two rocking chairs. Large glass doors offer glimpses into the interior, while warm lights enhance the inviting ambiance of the entryway. Steps lead up from a gravel path to the porch.

Cabin in Logan

Riverfront cabin and mini campground

Relax with the whole family at this beautiful Cabin. A very peaceful place to stay. Sits on the Guyandotte River that's great for kayaking. Very close to the Hatfield McCoy Bear Wallow trailhead. Unload your ATV and hit the trail. Restaurant on site and also very close to a car wash. If you need a place to stay for the holidays while visiting family, this is the place for you! Just a couple of miles from Chief Logan State Park .

5 out of 5 average rating, 36 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.

Apartment in Pikeville

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

**Ideal Retreat for Professionals: Cozy 2 Bed near Pikeville Medical Center & UPike** Welcome to our stylish and comfortable one-bedroom apartment, thoughtfully designed with traveling professionals in mind! Our newly furnished and recently remodeled space boasts two queen beds with memory foam mattresses, ensuring a restful night's sleep after a busy day at work.

4.68 out of 5 average rating, 53 reviews

A comfortable seating area features a dark sofa adorned with contrasting plaid pillows. A wall-mounted television is positioned above a decorative shelf displaying a plant and a welcome sign. Natural light enters through nearby windows partially covered by dark curtains.

Cabin in Williamson

Hillbilly Hideout-The Cove

Whether you're looking to ride the Hatfield-McCoy Trails or plan a weekend getaway, this cabin is perfect for you! Hillbilly Hideout 2 ( The Cove ) is located in historical downtown Williamson, just 0.3 miles from the Trail #10 entrance. There are several restaurants and convenience stores within walking distance. Come Hideout with us! www.hillbillyhideout.com

5 out of 5 average rating, 4 reviews

Home in Matewan

The Wild & Wonderful

Plan your next stay at the Wild and Wonderful. It’s a newly updated home with three bedrooms, two bathrooms, and enough beds to sleep around 10 people. Plenty of parking for at least 2 trucks and trailers. More can fit but it is a little tighter. The Hatfield and McCoy trails are within a hundred feet. It is also located very close to the town of Matewan.

Popular amenities for Williamson family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Cabin in Chapmanville

HillBilly HiltonDeluxe Log Cabin Rental

A warmly designed game room features wood-paneled walls and a polished hardwood floor. A pool table occupies one side, while a comfortable leather sofa is arranged nearby. A checker table is visible, accompanied by an arcade game machine, creating an inviting space for entertainment.

Cabin in Chapmanville

Almost Heaven Deluxe Log Cabin

4.8 out of 5 average rating, 15 reviews

The sleeping area features a queen-sized bed adorned with a muted animal print comforter. Light wood paneling complements the warm-toned flooring. A ceiling fan circulates air, while soft bedding is neatly stacked on a nearby shelf. Natural light filters through a window covered by light curtains.

Cabin in Delbarton

"The Cabin"

Place to stay in Williamson

The cottage stands nestled among trees, with a welcoming exterior illuminated by soft lighting at dusk. A well-kept walkway leads to double glass doors framed by inviting outdoor seating areas, creating an accessible entry point to the home.

4.99 out of 5 average rating, 103 reviews

The Red Dog Cottage In The Woods w/ Hot Tub

Two off-road vehicles are parked in front of a single-story modular home. The home features large windows, a covered porch with steps leading to the entrance, and is surrounded by lush greenery. Natural light is evident in the area, enhancing the inviting outdoor space.

Home in Matewan

4.6 out of 5 average rating, 40 reviews

Unit C: HOT TUB 20 Sec Ride to Trails, Sleeps 8!

4.99 out of 5 average rating, 83 reviews

The living area features comfortable seating with a recliner and a spacious couch arranged around a central wooden coffee table. Natural light enters through the windows adorned with light curtains, and a decorative wall piece adds a subtle touch to the neutral-colored walls.

Home in Gilbert

The River Lodge

4.71 out of 5 average rating, 14 reviews

A casual living area features a comfortable sofa and an arcade game in the background. A rustic wooden dining table with chairs is situated in front of a large window draped with light blue curtains. A decorative fireplace adds character to the room.

Home in Williamson

Hillbilly Hideout The Retreat

A spacious room is highlighted by a custom pool table made from natural wood, complemented by a rustic wood ceiling and walls. A cozy leather recliner is positioned nearby, while decorative elements include carved wood accents and framed artwork. Natural light enters through windows, enhancing the inviting atmosphere.

Cabin in Chapmanville

Bearly Ruff-N-It Deluxe Log Cabin

Family- and pet-friendly home rentals

4.97 out of 5 average rating, 31 reviews

A two-story house features a covered porch with a railing, spanning the front. Clusters of trees are visible in the background, and a grassy area is situated below. A white picket fence and gravel driveway form the property's boundary.

Home in Williamson

The Mountain Mama

4.89 out of 5 average rating, 105 reviews

The cabin's exterior is softly illuminated at twilight, featuring a welcoming entrance with colorful doors. A stone pathway leads to a cozy seating area surrounded by greenery and potted plants. The car parked in the foreground adds to the homey feel of the location.

Cabin in Prestonsburg

The Eagle's Rest Country Cabin

5 out of 5 average rating, 12 reviews

A spacious property is surrounded by lush green trees, with a gravel driveway leading to a two-car garage. The house features a bright yellow exterior, which contrasts with the natural surroundings, while a clear blue sky adds to the open feel of the setting.

Cabin in McCarr

Trailhead Riverfront Cabin

4.96 out of 5 average rating, 50 reviews

A cozy living room area features a dark sofa with decorative pillows, set against light wood paneling. A wooden coffee table and side tables are included, with a vase of flowers on one. Black curtains frame a window, and a television is mounted on the wall.

Cottage in Varney

3 bedroom house with ATV trail access.

4.96 out of 5 average rating, 24 reviews

A cabin entrance is framed by wooden steps leading to a covered porch with two rocking chairs. Behind, a rocky cliff provides a natural backdrop, and the ground is covered in gravel and scattered leaves.

Cabin in Delbarton

Cozy cabin, easy trail access

4.84 out of 5 average rating, 37 reviews

A single-story home is shown with a welcoming front porch supported by wooden posts. Two chairs are positioned on the porch, overlooking a grassy area surrounded by trees. Large windows provide natural light to the interior, enhancing the home's connection to the outdoors.

Home in Williamson

The Coal Miners Daughter

5 out of 5 average rating, 5 reviews

A two-story house with a wooden staircase leading to a covered porch extends across the front. The exterior is clad in gray siding, while the foundation is constructed with stone. A gravel area surrounds the home, enhanced by green grass and the natural landscape.

Home in Switzer

Nan's Place

4.74 out of 5 average rating, 19 reviews

A rustic kitchen area is showcased, featuring a refrigerator, microwave, and a sink. A small, gray countertop is paired with two dark wood stools. Fresh flowers in a vase add a touch of color to the scene, complemented by wood-paneled walls.

Place to stay in Ethel

Cottage at campground

Family-friendly home rentals with a pool

A covered hot tub is illuminated with soft blue lights, adjacent to a built-in gas grill. Additional images depict a well-lit outdoor dining area with chairs, a gravel path leading to a spacious green yard, and a clear above-ground pool with step access.

Home in Red Jacket

4.68 out of 5 average rating, 57 reviews

Benchmark Hideout L.L.C.

4.88 out of 5 average rating, 96 reviews

The image displays a private inground swimming pool surrounded by a concrete patio. A wooden deck with multiple levels is visible behind the pool, featuring large windows. Outdoor seating is arranged nearby, complemented by a blue umbrella and a swing set. Lush greenery provides a natural backdrop.

Cabin in Stollings

Hidden Retreat Cabin Mountain View Pool OpensMay30

4.92 out of 5 average rating, 13 reviews

Cabin in McCarr

River Road Retreat

4.79 out of 5 average rating, 42 reviews

A sparkling saltwater pool reflects clear blue skies, surrounded by a stone deck. The back of the residence features red doors flanked by potted plants. A hammock is positioned nearby, adding to the outdoor relaxation space.

Home in Matewan

Trailhead Haven