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!

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.

Mama Bear's Den - perfect location for the trails!

Mama Bears Den is the Perfect Location to Visit the Hatfield and McCoy Trails offering access to not only one but two different trail systems (Devil Anse & Rockhouse) within a mile of the property! Devil Anse connects with a Third trial system (Buffalo) offering days of trials with no need to trailer to other locations! Relax on the porch or by the fire pits while cooking on the grills by a scenic creek! While here visit the gravesite or museum of Devil Anse, just a short walking distance away.

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!

* Large Coded Access Garage Area Included*

Discover your perfect getaway! The Decked Out Den is a 3-bed, 2-bath 1400sqft home with a detached 30'x30' garage to protect your machines from the weather. Enjoy ample parking, a spacious deck, and a cozy living room. Conveniently located near multiple trail access points, it’s just a short ride to Matewan or Delbarton—no need to trailer. Explore Buffalo, Devil's Anse, or Rockhouse trail systems. Book now for an adventure-filled stay with all the comforts of home!

The Red Dog Cottage In The Woods w/ Hot Tub

Private parking with a 30ft walking bridge overlooking a water stream to lead you to the cottage. Queen bedroom downstairs; spiral staircase takes you to your loft queen bedroom; one full bath; full kitchen; TV/WIFI; indoor loft hammock; wrap around covered porch; tree covered outdoor shower area with hot tub; covered dining back porch. Large fire pit area with dried fire wood. Large 12ft x 12ft outdoor hammock beside fire pit. Park Series charcoal grill outside.

Creekside Country NEST-Unit B-Access to Bearwallow

Nestled in the beautiful Appalachian Mountains, my Nest is perfect for outdoor enthusiasts. Enjoy quick access to Hatfield–McCoy Trails, plus great hiking, fishing, and kayaking. The unit features a full kitchen, spacious living room, two bedrooms, a stocked bathroom, washer & dryer, charcoal grill, picnic table, firepit, and ample parking for ATVs and trailers—comfort and adventure in one place!

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

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!

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.

Cozy & Charming between Pikeville/Prestonsburg

Quiet and peaceful location just off of US 23 highway. Centrally located between Pikeville and Prestonsburg. 10 mins from City of Pikeville and 15 minutes from City of Prestonsburg Minutes from shopping and restaurants. Beautiful lakes and parks close by.

Riverside Heights

The whole group will enjoy easy access to everything from this centrally located place. This unit is only a short drive from Pikeville Medical Center and the University of Pikeville. There are a few steps to access this unit (pictured below).