Holiday rentals with outdoor seating in Pike County

Papa Bear’s Den - perfect location for the trails!

Papa 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

Modern Escape

Modern Escape at Harvey's Hideaway Haven is a contemporary retreat that offers all the comforts of home in a compact and stylish package. (160 sq. ft. of living space) At Harvey's Hideaway Haven, you'll 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 PMC, Upike and the Expo center!

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

The Carolyn House

The whole group will be comfortable in this spacious and unique space. Enjoy your stay at this 3 Bedroom 3.5 bath estate home located minutes from downtown Pikeville. You truly get the best of both worlds being so close to downtown but enjoying the privacy this space provides. No more than 8 guests are allowed on property unless approved by the host. Parties can be approved with a fee. Pool is currently unavailable for use Stairs are necessary to access upper level and laundry.

Mountain view country home

This stylish place to stay is perfect for group trips. This cozy country home is nestled on a hill, just walking distance from downtown Pikeville and the hospital. Lots of privacy with beautiful mountain views from a big front porch and a soothing waterfall can be seen after a nice rain from the upstairs screened in porch. Great for large groups or families. Walking distance to Appalachian wireless arena, UPIKE,Med ,Optometry, Nursing Schools, and Pikeville Medical Center.

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.

Sully's House

Sully's Home is designed for riders who prefer a more intimate setting like being in your own home. This home is less than a mile from the Devil Anse trailhead and downtown Matewan. Come off the trails and in 2 minutes you are back at your home away to fix meals in the fully stocked kitchen, or Blackstone Griddle. Then relax on the front porch, or by the fire pit, or just watch some TV. Max 5 guests, rent Sully's House and both cabins if you need added space.

The Hillbilly Hideout

Tucked in the trees and just minutes from the Hillbilly Trail System, this modern cabin is your go-to basecamp for off-road adventure and mountain downtime. Whether you’re here to ride, relax, or both—you’ll have all the comforts of home without losin’ that good ol’ backwoods feel. With room for up to 6 guests, a full kitchen, fire pit, and plenty of space for your trailer and SxS. We have two neighboring cabins for larger groups.

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

Driftwood Studio Cottage Hot Tub | Pet Friendly

Driftwood Studio Cottage is your basecamp for adventure. A small, private studio located on a multi-family property along the Russell Fork River in downtown Elkhorn City. Start your mornings with coffee on the deck as the river rushes by, spend your days chasing adventure in the mountains, and end your evenings soaking in the hot tub with the water just below.

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!

Hawks Nest

Take a break and unwind at this peaceful oasis. Great getaway for a peaceful night or weekend stay! Located in the heart of the Hatfield and McCoy family feud ! Come stay and visit the Hatfield and McCoy sites ! Just minutes from Matewan WV ! Come and ride the trails and relax !