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Nestled between dramatic Appalachian ridges, this historic coal town invites visitors to explore the fascinating Hatfield-McCoy feud sites and engineering marvel of the Pikeville Cut-Through. Outdoor enthusiasts can hike Breaks Interstate Park's breathtaking gorge trails, while downtown's Appalachian cuisine and mountain music scene offer authentic local flavors after a day's adventure.

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- Comfort Suites Prestonsburg West
- Days Inn by Wyndham Paintsville
- Quality Inn & Suites Prestonsburg next to Mountain Arts Center
- Sleep Inn & Suites Clintwood
- Gateway To The Breaks Motel
- Comfort Inn & Suites Grundy
- Brookshire Inn
- Nice private home in Matewan, close to trails! Hottub, Pool, fire pits & games!
- 11 bed 7 bath large home and able to ride right from the home to the HMT trails
- Luxury Estate nestled atop stunning mountaintop golf course!
- Large 4BR Buffalo Mountain Retreat in Williamson with pool, Ride to trails
- Trail Riders Retreat! Hatfield McCoy Trails. Private Pool. Loads of Parking!
- NEW PARADISE RETREAT - Hatfield Mccoy Trails - Rent 1-3 Cabins, Sleep up to 18
- Mountain Laurel House
- Appalachian Hideaways
- Recently Updated - Cozy Creekside Tiny Home w/ Full Kitchen; Walk to Distillery
- The Mountain Magnolia *Hot tub on private deck*
- Large spacious house with ample parking for large groups.
- The Red Dog Chalet Couples Retreat w/ Hot Tub
- Creekside Lodge–Trailside Stay w/Firepit, Sleeps 10