Holiday rentals with outdoor seating in Pike County

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!

The Red Dog Chalet Couples Retreat w/ Hot Tub

Private parking area with a beautiful covered walking bridge that leads you to the beautiful getaway with a spiral staircase taking you to the 2nd story covered porch areas with a wraparound walking deck. Queen size loft bed. Kitchenette area on main floor. TV/WIFI. Enjoy the two person copper tub. Under the chalet, there is the private outdoor shower; hot tub and bed swing. Large firepit area with fire wood. Large 12ft x 12ft hammock behind fire pit area. Park Series charcoal grill outside.

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!

Charming 5BR Near Breaks < 10 min

Welcome the "The Holly House." This mid century modern home has been upgraded with your comfort in mind. Whether you're enjoying a quiet moment outside, gathered with friends and family in the living room, or enjoying a movie in the game room there is something here for everyone. We are conveniently located near the Breaks Interstate Park. Simply take a 5 minute drive to access hiking trails, kayaking, live theatre, a water park, horse back riding, rock climbing, fishing and zip lining.

Entire house Privately located 4 bedroom

Private 4 bedroom house equipped with full kitchen, (2) living spaces, dining, 2 full baths, laundry room, kitchenette downstair. Outdoor pavilion area with with charcoal and gas grill, corn hole and fire pit. Free WiFi. Ride straight to buffalo and devil anse trails less than a mile. Or downtown Williamson is 2 miles. 5 access points from house on ATV. Note this house is on a hill. Plenty of parking to hold 5-6 trucks. We have an overflow lot to accommodate oversized trailers if needed.

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 Hilltop House

The Hilltop House is located less than a half mile from the Devil Anse trailhead and under 1 mile from downtown Matewan WV. This beautifully remodeled home (2023) is designed for riders that want more from where they stay, The Hilltop house has great privacy and beautiful views in addition to being packed with features both inside and out. This home is designed for a maximum of 6 guests, please do not book if you have more than 6 in your party without hosts prior approval.

Relaxing stay at Creekside Lodge

Wonderful, homey getaway beside flowing creek with little traffic, less than a mile from the Buffalo Mountain Trailhead. This is not just a place for trail riders but has been used by people attending family reunions and local festivals. Creekside Lodge is within the town limits of Delbarton where there are several restaurants, a small general store, and soon to open Dollar General. Trail riders will pass a local gas station on the way to the trail head.

Wild Horse Trail Lodge @ HMT

The Wild Horse Trail Lodge is conveniently located on the Tug Fork River. We are 7 miles from Matewan WV, Devils Anse Hatfield & McCoy trail heads. Directly across the street, you’ll find access to the KY Outlaw trails, home to many wild horse herds and miles of endless ATV trails. Inside the home you’ll find comfortable accommodations for 8 guests. On the rear of the house, is a 40ft deck over looking the river. Riding, Fishing, swimming, & more!

Luxury Lodge in the Mountains | ATV Trails

Mountain Brook & Company lodge is privately owned and located in the heart of West Virginia. This rental unit includes three bedrooms, 2 full bathrooms/ two half bathrooms, and comfortably sleeps six. We are conveniently situated close to the Hatfield McCoy (Buffalo Trailhead) and offer the perfect amenities for a weekend retreat, romantic getaway or a vacation full of adventure.

Mountain Escape

Kick back and relax in this calm, stylish home. Come and relax in this 3 bedroom mountain family charm nestled in the hills of Eastern Kentucky. Pretend you are lost in an enchanted forest as you perch on a log or curl up on the front porch swing. Soak in the tub, then fall asleep in one of the three comfortable beds. When you wake up, the coffee machine awaits.