Family-friendly holiday rentals 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!

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.

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

Buffalo Playhouse w/game room Easy trail access

Bring your large group for lots of fun! Plenty of parking for 6 trucks & trailers. Game room w/fast &furious arcade game, air hockey- Wii U w/Mario Kart & board games. Relax with A 65-inch Roku tv in the family room that seats 8. Everyone sleeps comfortable in 1 of 9 beds with 15 bed positions plus 2 futons! 2.5 miles to where trail 11 & 12 cross Route 52 on the Buffalo Mountain Trail. 3.5 Miles to the Buffalo Mountain trailhead, 1 mile from outlaw trails. Come, unwind and play hard!

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.

New Paint & Flooring - Cozy Creekside Tiny Home

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!

Ridge Runners Suite #4

This recently renovated 1BR/1BA apartment features a queen bed, full kitchenette, cozy living area with a pull-out sofa, electric fireplace, and 50" TV. Enjoy mountain views, a coffee bar, and easy access to shops, dining, and trails. We're just off Route 119 on the Kentucky side by Williamson, WV—quiet, convenient, and trailer-friendly. We are within walking distance of stores and groceries, or you can relax on the deck. We offer clean, comfortable, convenient, and charming lodging!

Backwoods Bungalow

Backwoods Bungalow at Harvey's Hideaway Haven is a rustic retreat designed to bring you closer to nature while offering the comforts of modern living. 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.

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

Rocky Top- Cabin at Billy Goat Mountain Village

We offer the absolute CLOSEST lodging to the Buffalo Mountain Trailhead on the historic Hatfield-McCoy Trail System. Rocky Top is perfect for any group looking for an Appalachian Mountains experience in a beautiful, custom-built cabin. Get muddy by day, enjoy luxury by night. We offer comfy beds, the softest linens, stocked kitchen with Keurig and ice maker, fire pit with free wood, outdoor grill, DirecTV, Wi-Fi, great cell service, and plenty of parking.

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

Cabin 1 -Saw’n Logs -Sleeps 8

Cabin 1 is centrally located between multiple trailheads Buffalo Mountain being the closest at only 1.6 miles away. This cabin has a spacious floor plan layout. The cabin theme is sawing logs. It has 3 king size beds with a pull out sofa. The cabin sets at the edge of the property with a wrap around porch giving an open view while enjoying morning coffee.