Holiday rentals in Pike County

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Top-rated holiday rentals in Pike County

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

A well-maintained golf course is visible, featuring a green with a flag positioned at the hole. Lush, rolling hills provide a scenic backdrop, framed by trees. Pathways and a nearby building with a porch are discernible in the distance, creating an inviting landscape.

Cottage in Breaks

4.9 out of 5 average rating, 91 reviews

Cozy Mountain Cottage Overlooking Golf Course

Slow down with the whole family in true Southern fashion at our cozy country cottage located in a rural mountain community. This three bedroom, two bath home overlooks Willowbrook public golf course and is just mintues from Breaks Interstate Park, home of "the Grand Canyon of the South." Local attractions include hiking and ATV trails, kayaking/white water rafting, ziplining, water park, picnic shelters, playgrounds & more! Winter guests are likely to encounter majestic views of wild elk grazing

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Top guest favourite

A spacious living and dining area features a wooden dining table surrounded by six chairs. A comfortable sofa and two armchairs are arranged for relaxation. Natural light streams in through large windows, highlighting the country-themed decor and the welcoming ambiance of the room.

Cabin in Williamson

4.98 out of 5 average rating, 45 reviews

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!

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Top guest favourite

A modern fireplace is set against a backdrop of light gray walls, featuring a white mantel with a decorative 'welcome' sign. Built-in benches flank the fireplace, providing additional seating space. The flooring utilizes a warm wood tone, adding comfort to the room.

Home in Varney

4.95 out of 5 average rating, 102 reviews

Miss Piggy’s Farmhouse HMT Trailhouse Rental

Peacefully located between Buffalo Mountain Trail and Devil Anse Trail at Varney, WV. Newly Renovated, Farmhouse Style, very clean, spacious. Backyard -porch, Outdoor Firepit, Blackstone Grill Front yard - large lighted porch w/ dining area Bedroom 1 - King Bed with Masterbath Bedroom 2- Queen Bed Bedroom 3 - Queen Beds 2nd Bathroom - Full Bathroom Living Room 1- Sofa Living Room 2- Sofa bed w/ 2- twin beds Washer & Dryer Full Kitchen Keurig ,Stove,Oven,Microwave, Toaster, Dishwasher

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Top guest favourite

A well-appointed kitchen is highlighted by a chevron-patterned wooden countertop, complemented by four high-backed stools. Light wooden cabinetry and modern appliances are visible in the background, providing a functional and inviting space for meal preparation and dining.

Flat in Haysi

5 out of 5 average rating, 19 reviews

Russell Fork River Lofts

Relax with the whole family at this peaceful and beautiful loft. If you are looking to explore the Breaks Interstate Park and the Crooked Road we would love to have you stay at our new renovated loft. This top floor loft features 1 bedroom with a queen bed and a queen sofa bed. A full kitchen and bathroom with shower tub combo with washer and dryer. The loft is 8 miles from the Breaks Interstate Park and is directly on the spearhead trail. Plenty of parking for all your vehicles and trailers.

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Guest favourite

Cottage in Varney

4.96 out of 5 average rating, 54 reviews

3 bedroom house with ATV trail access.

This newly renovated house is located just minutes between the very popular Hatfield McCoy Trail heads for Buffalo Mountain and Devil Anse. The Dollar General grocery store is also located within 1 mile for all of your grocery needs. This entire house offers 3 bedrooms with 5 beds, full kitchen, living room, washer and dryer, bathroom, fire pit, ping pong table, outdoor grill, and free parking with room for a large trailer. Additional amenities include WiFi, TV, and a spacious backyard.

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Guest favourite

A large covered deck showcases wooden flooring and a railing. Several seating options are arranged in pairs, alongside a wooden table set for dining. Lush greenery is visible in the background, enhancing the serene river view. Natural light provides a warm, inviting ambiance.

Home in Matewan

5 out of 5 average rating, 18 reviews

River View- Matewan - 1 mi to trail - easy parking

Enjoy gorgeous views of the Tug River from a HUGE covered deck & relax at this peaceful getaway. Located just 1 mile from the Devil Anse trailhead of the Hatfield & McCoy Trail system (Buffalo & Rockhouse, WV/KY Outlaw trails access) and downtown Matewan. Kitchen with full-size fridge, microwave, coffee pot & grill (No stove). Washer & dryer. All linens provided. Flat ground parking for your truck & trailer is available. Sleeps up to 6. Neighboring properties available for large groups.

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Guest favourite

Flat in McDowell

5 out of 5 average rating, 18 reviews

Tranquil 2-bedroom apartment

Consider this lovely apartment your home away from home while you visit McDowell. With queen beds in the 2 bedrooms and a cozy living room with a futon, there's plenty of space for guests to relax, including a front porch. Enjoy the beautiful bathtub in the bathroom and take advantage of amenities like heating, AC, Wi-Fi, and a washing machine. A welcoming retreat in the heart of the city, this apartment is a great place to call home base while you're away. We hope you enjoy your stay.

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Guest favourite

The cottage stands nestled among trees, with a welcoming exterior illuminated by soft lighting at dusk. A well-kept walkway leads to double glass doors framed by inviting outdoor seating areas, creating an accessible entry point to the home.

Place to stay in Williamson

4.98 out of 5 average rating, 125 reviews

The Red Dog Cottage In The Woods w/ Hot Tub

Private parking with a 30ft covered 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 covered hot tub; covered dining back porch. Large fire pit area with dried fire wood. Large 12ft x 12ft outdoor hammock behind fire pit. Park Series charcoal grill outside.

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Superhost

A spacious living area features a plaid sectional sofa adorned with red accent pillows. A rustic wooden coffee table is positioned in the center. Two lamps stand on either side, providing additional lighting, beside a doorway that leads to other areas of the apartment.

Flat in Pikeville

4.9 out of 5 average rating, 246 reviews

Sweet Dreams

* If you book for 7 days or more, you will receive a 20% discount off your stay. If you’re in town on business, to visit family or just traveling through, this 2ND FLOOR APT is perfect for you. Enjoy a full kitchen & onsite laundry facility. You’ll get a good nights sleep in a quiet space, on high quality mattresses. We are conveniently located just down the street from a Food City. We have a work desk & free WIFI. We’re just a 5 minute drive from downtown Pikeville.

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Top guest favourite

An aerial view of the Wild Horse Trail Lodge reveals a well-maintained property nestled along the Tug Fork River. Grassy areas surround the house, featuring a fire pit and ample parking space for vehicles. Nearby, trees offer natural shade in the tranquil setting.

Home in Freeburn

5 out of 5 average rating, 12 reviews

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!

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Top guest favourite

A cozy living area features warm wooden walls and a gray sofa, complemented by decorative pillows. A blue accent chair adds a pop of color, while a large plant brings a touch of nature indoors. Light streams in from a skylight above.

Cabin in Pikeville

5 out of 5 average rating, 41 reviews

Inspiration Station

Inspiration Station at Harvey's Hideaway Haven is designed to uplift your spirit and ignite your inner drive. You will 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 Pikeville Medical Center, Upike and The Appalachian Wireless arena!

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Superhost

Flat in Pikeville

4.83 out of 5 average rating, 12 reviews

The Loft at Caney Creek

Welcome to your newly renovated, cozy 2nd-floor studio . This comfortable hideaway offers the perfect blend of relaxation and convenience, making it ideal for travelers, trail riders, workers, and weekend explorers. Prime location right off US Hwy 23 South — just 15 minutes from Pikeville for dining, shopping, events, and hospitals and only 2 miles from the Hillbilly Hills trail entrance in Dorton, KY.

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