Family-friendly holiday rentals in Williamson

5 out of 5 average rating, 20 reviews

The exterior of a modern building is shown, featuring a dark metal facade with wood accents. Several doors with small square windows are visible, accompanied by outdoor seating. A wooden deck extends along the front, enhancing the inviting entrance.

Flat in Lenore

Hidden Jewell Studio Suite #2 - 2BD/1BA on Outlaws

Cozy 4 private unit suite-style retreat sleeps 15 w/ full bathrooms, kitchenettes & comfy temperpedic beds. Located right on the Outlaws - no trailering - that connect to HMT, just minutes from the historic Dingess Tunnel - "America's Bloodiest Tunnel" Enjoy fishing at Laurel Lake that's stocked w/ fish. Outdoors unwind by the firepit, grill & picnic area under the stars. Large parking lot for trucks & trailers. A serene escape w/ a touch of history & lots of adventure *Tablet available to rent

5 out of 5 average rating, 35 reviews

A spacious living and dining area features a wooden dining table surrounded by six chairs. A comfortable sofa and two armchairs are arranged for relaxation. Natural light streams in through large windows, highlighting the country-themed decor and the welcoming ambiance of the room.

Cabin in Williamson

Trail Riders Retreat with private in-ground pool

If you’re looking for a place to relax and unwind on either a huge front porch or a cool, cozy secluded back porch after a long day on the Hatfield – McCoy Trails, you’ve found the perfect place. With a constant cool, mountain breeze and the sounds of nature, you’re sure to enjoy your stay here at Trail Riders Retreat located in Lick Creek, Williamson, WV. This house is conveniently located within 3.5 miles of shopping and dining and is approximately 1.5 miles from #26 trail entrance. Pool Open!

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.

4.82 out of 5 average rating, 22 reviews

A single-story home is depicted from the front, featuring a welcoming porch with wooden steps. Large windows are adorned with dark shutters, allowing natural light inside. Surrounding greenery complements the exterior, and a gentle hillside is visible in the background.

Home in Williamson

Lil’ Owls Hideout

Located in Chattaroy, WV., Outside of Williamson, WV. 25 Mins from Matewan, WV. We are about 4.4 miles from the Buffalo Mountain Trail Head, access to Buffalo Moutain Trail 10 (WV Swing Overlook) is about 3.5 Miles away & Trail 12 about 3 Miles. About 2 Miles from Outlaw trails. Access to Devil Anse & Rockhouse Trails. The closest gas station is less than 3 miles away, who sells Hatfield & McCoy Trail passes. We are less than 5 Miles away from Shopping, Restaurants, & additional Gas Stations.

4.98 out of 5 average rating, 62 reviews

The living area features a spacious sofa, wood coffee table, and an electric fireplace. A dining table for four is visible, along with a kitchenette that includes a refrigerator. Lighting is provided by a ceiling fan and a nearby table lamp.

Flat in Belfry

Ridge Runners Suite #1

This is a 1 bed/1 ba suite with a queen bedroom. (Also see listings for #2, #3 & #4). Kitchenette with coffee bar, microwave, fridge, plates, glasses, silverware, etc, & table for 4. Bathroom with shower, towels, shampoo & soap. Living room with queen pull-out couch, sofa table, electric fireplace, & TV. Easy parking! Just off Route 119 on flat ground. Mountain views yet within walking distance of groceries, banks, a mall, & restaurants. Comfort, cleanliness, charm, & convenience!

4.93 out of 5 average rating, 126 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.

Flat 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, 112 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.

5 out of 5 average rating, 5 reviews

The kitchen area features wooden cabinetry and a long countertop with a sink and microwave. A two-burner stovetop is present, alongside a toaster and a coffee maker. Shelves display various utensils and glassware, while a trash can and high stool are positioned nearby.

Cabin in Pikeville

Wanderer’s Oasis

Wanderer's Oasis at Harvey's Hideaway Haven is a Boho-themed studio cabin retreat that features a Queen size bed! (280 sq ft of living space) 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, frogs 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, 174 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 .

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

4.68 out of 5 average rating, 53 reviews

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

4.96 out of 5 average rating, 48 reviews

A dining area features a wooden table surrounded by six chairs, arranged for family meals. A white refrigerator and an oven are situated alongside wooden cabinetry, with a coffee maker and other appliances on the countertop. Natural light filters through a window, partially covered by light curtains.

Home in Belfry

Bourbon House

The prime place for outdoor enthusiasts. Minutes from the Hatfield McCoy trail systems, the Kentucky Hillbilly trail systems, kayaking and fishing in the tug fork river. Local amenities such as the mall, restaurants, gas stations and grocery stores. All of this helps to make your stay heavenly!

4.88 out of 5 average rating, 17 reviews

A restful bedroom features a full-sized bed dressed in soft linens and a vibrant throw. Natural light floods the space through a window with blinds. A small desk and chair are present, alongside a mirror reflecting the room's bright, airy feel.

Flat in Pikeville

Convenient & Cozy | Free Laundry, Wi-Fi, & Parking

Welcome to your home away from home - the perfect blend of comfort, convenience, and style for the traveling professional or those seeking a long-term stay. Our newly furnished one-bedroom apartment offers a tranquil retreat with all the modern amenities you need to live, work, and relax.

Popular amenities for Williamson family-friendly rentals

Kitchen

Wifi

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, 104 reviews

The Red Dog Cottage In The Woods w/ Hot Tub

4.59 out of 5 average rating, 41 reviews

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

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

4.96 out of 5 average rating, 23 reviews

A spacious lodge exterior is shown, featuring a covered porch with multiple black rocking chairs arranged for relaxation. Gravel surrounds the lodge, and the backdrop showcases a forested hill with bare trees, indicating a tranquil, natural setting.

Cabin in Matewan

Trailside Lodge, 10 Sec to Trail, Hot Tub+Fire Pit

4.81 out of 5 average rating, 59 reviews

A hot tub is situated on a wooden deck surrounded by lush greenery. Trees and shrubs create a peaceful backdrop, while steps lead down to the grassy area. The hot tub appears to be ready for relaxation, with steam gently rising from the surface.

Home in Chapmanville

Chapmanville House, Hatfields Getaway

4.99 out of 5 average rating, 84 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

Family- and pet-friendly home rentals

4.89 out of 5 average rating, 9 reviews

A cozy, single-story brick house is surrounded by green grass and a well-maintained gravel area. A fenced yard offers space for relaxation, while trees and hills provide a scenic backdrop. The entrance features a small gate, enhancing the property’s charm.

Home in Matewan

Matewan Rider's Retreat with Garage Access!

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

4.95 out of 5 average rating, 37 reviews

A private four-bedroom house is situated on a hillside, featuring a green exterior. The entrance showcases a stone facade and a decorative door with a circular window. Large windows are present, allowing natural light to fill the living spaces, surrounded by lush trees.

Home in Williamson

Entire house Privately located 4 bedroom

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

4.9 out of 5 average rating, 39 reviews

A spacious country house is set against a backdrop of wooded hills, characterized by a stone and wood exterior. Large windows are featured prominently, allowing natural light to fill the interior. The well-maintained lawn is bordered by subtle landscaping elements.

Guest house in Grundy

Your Private Mountain Retreat Awaits!

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

4.66 out of 5 average rating, 62 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, 43 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