Vacation rentals in South Williamson

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Top-rated vacation rentals in South Williamson

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Top guest favorite
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
5 out of 5 average rating, 35 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!

Top guest favorite
A single-story cabin with a welcoming front porch is illuminated by soft lighting. Colorful adirondack chairs are arranged along the porch, overlooking a gravel area. The structure features air conditioning units on each side, with surrounding trees in the background.
Cabin in Matewan
5 out of 5 average rating, 40 reviews

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.

Guest favorite
A private four-bedroom house is situated on a hillside, featuring a green exterior. The entrance showcases a stone facade and a decorative door with a circular window. Large windows are present, allowing natural light to fill the living spaces, surrounded by lush trees.
Home in Williamson
4.95 out of 5 average rating, 37 reviews

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.

Top guest favorite
Home in Williamson
4.95 out of 5 average rating, 22 reviews

Rosie's Roadhouse-Cabin at Billy Goat Mtn. Village

The absolute CLOSEST lodging to the Buffalo Mountain Trailhead at the heart of the Hatfield-McCoy Trail System. Perfect for anyone looking for an "Appalachian experience" in a beautiful and unique cabin. Get muddy by day and enjoy luxury by night. Comfy beds, the softest linens, fully stocked kitchen with Keurig and ice maker, fire pit, outdoor grills, corn hole, vintage arcade games, DirecTV, fireplace, laundry, FREE WIFI, GREAT cell service, PLENTY of parking, touch pad door locks.

Guest favorite
A living area features a plush couch and a wooden coffee table, complemented by a small dining table with three stools. A ceiling fan provides air circulation, while natural light fills the space through a nearby window. The kitchenette is partially visible in the background.
Apartment in Belfry
5 out of 5 average rating, 42 reviews

Ridge Runners Suite #4

This recently renovated 1BR/1BA apartment features a queen bed, full kitchenette, cozy living area with a pull-out sofa, electric fireplace, and 50" TV. Enjoy mountain views, a coffee bar, and easy access to shops, dining, and trails. We're just off Route 119 on the Kentucky side by Williamson, WV—quiet, convenient, and trailer-friendly. We are within walking distance of stores and groceries, or you can relax on the deck. We offer clean, comfortable, convenient, and charming lodging!

Top guest favorite
A spacious living area features a comfortable brown leather sofa and a circular chair. A 58" TV is mounted on the wall, accompanied by a wooden entertainment unit. Natural light filters through sheer curtains, and decorative artwork is displayed on the walls.
Home in Prestonsburg
4.96 out of 5 average rating, 129 reviews

The Shotgun House

Enjoy your stay at the Shotgun house located in the heart of Prestonsburg within walking distance to a popular restaurant and downtown shopping. This cozy house offers a 58" TV and playstation in the living and also a 50" TV in the bedroom. Relax outside on a covered porch and enjoy the occasional local live music. Located close to the Prestonsburg Passage Trail, Mountain Arts Center, Middle Creek National Battlefield, Pikeville Exp Center and a short drive to the Red River Gorge.

Top guest favorite
Home in South Williamson
5 out of 5 average rating, 13 reviews

The Depot -Luxury Rental

Your group will enjoy easy access to everything from this centrally located place. Our house is ideal for traveling medical/business professionals, or families visiting the area. It is not suitable for ATV trail riders because we have no parking space available for trailers/ UTV’s, or SxS’s. We are 0.6 miles from Mingo County Courthouse and Williamson Health and Wellness Center, 1.3 miles to Tug Valley ARH Medical Center, 30 minutes drive to Pikeville Medical Center.

Top guest favorite
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
4.99 out of 5 average rating, 106 reviews

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.

Guest favorite
The cabin's exterior is illuminated in the evening light, featuring a stone facade and a prominent logo. Pathways are paved, and gravel surrounds the building, creating a welcoming approach. Surrounding trees are visible in the background, enhancing the cabin's secluded charm.
Cabin in Belfry
5 out of 5 average rating, 9 reviews

Elkview Suite-Buffalo Trail System HMT

Discover the ultimate ATV retreat at Hidden Mountain ATV Resort's Little Elk Cabin. Nestled just 1/2 mile from the renowned Buffalo Trail system and Williamson, WV, this cabin provides the perfect blend of convenience and comfort. Immerse yourself in Williamson's rich history and explore its abundance of restaurants, shopping havens, and gas stations, ensuring you're well-prepared for your thrilling off-roading escapade on the iconic Hatfield McCoy Trail system.

Top guest favorite
A welcoming front porch is framed by a green lawn scattered with fallen leaves. The porch features simple wooden steps and a stone foundation. A decorative pumpkin is placed near a potted plant, with trees adding natural greenery to the surroundings.
Home in Delbarton
5 out of 5 average rating, 29 reviews

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.

Top guest favorite
An open living area features vaulted wooden ceilings and hardwood floors. Large windows allow natural light to fill the space. A seating arrangement with leather sofas is positioned near a patterned area rug, complemented by a dining table. Kitchen appliances are visible in the background.
Home in Barnabus
4.95 out of 5 average rating, 22 reviews

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.

Guest favorite
Home in Matewan
5 out of 5 average rating, 9 reviews

The Wild & Wonderful

Plan your next stay at the Wild and Wonderful. It’s a newly updated home with three bedrooms, two bathrooms, and enough beds to sleep around 10 people. Plenty of parking for at least 2 trucks and trailers. More can fit but it is a little tighter. The Hatfield and McCoy trails are within a hundred feet. It is also located very close to the town of Matewan. 

Popular amenities for South Williamson vacation rentals

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