Holiday rentals in Toler

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Top-rated holiday rentals in Toler

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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
5 out of 5 average rating, 32 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 favourite
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, 38 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.

Top guest favourite
A two-bedroom home with a welcoming red door is set against a backdrop of green hills. The exterior features beige siding and a metal roof, with a paved driveway leading to the entrance. Neatly manicured shrubs and trees enhance the outdoor space.
Home in Matewan
4.98 out of 5 average rating, 45 reviews

Almost Heaven Vacations

We have a beautiful two-bedroom, one-bath home that comfortably sleeps four located near the Hatfield-McCoy Trails in North Matewan, West Virginia. We provide a clean, cozy home away from home for your ATV trip. We have a fully stocked kitchen, charcoal grill, picnic area and plenty of parking/turning space for your equipment. Our house is located less than one mile from the Devil Anse Trailhead (which connects to Buffalo and Rock House trailheads) Book your stay today! We’d love to have you.

Top guest favourite
The living area features a spacious sofa, wood coffee table, and an electric fireplace. A dining table for four is visible, along with a kitchenette that includes a refrigerator. Lighting is provided by a ceiling fan and a nearby table lamp.
Flat in Belfry
4.98 out of 5 average rating, 60 reviews

Ridge Runners Suite #1

This is a 1 bed/1 ba suite with a queen bedroom. (Also see listings for #2, #3 & #4). Kitchenette with coffee bar, microwave, fridge, plates, glasses, silverware, etc, & table for 4. Bathroom with shower, towels, shampoo & soap. Living room with queen pull-out couch, sofa table, electric fireplace, & TV. Easy parking! Just off Route 119 on flat ground. Mountain views yet within walking distance of groceries, banks, a mall, & restaurants. Comfort, cleanliness, charm, & convenience!

Top guest favourite
The exterior of the chalet features a two-story structure surrounded by lush greenery. A covered porch extends from the second level, and a staircase leads down to the landscaped yard. Pathways and railings create a welcoming access to the home.
Treehouse in Williamson
4.99 out of 5 average rating, 108 reviews

The Red Dog Chalet Couples Retreat w/ Hot Tub

Trailer access pull-thru private parking area with a beautiful lighted walking bridge that leads you to the chalet. A beautiful getaway with a spiral staircase leading you to the 2nd story covered porch with a wraparound walking deck. Large firepit area with dried fire wood. Large 12ft by 12ft hammock beside fire pit area. Two person copper tub; private outdoor shower; hot tub and large bed swing. Loft bedroom. Free WIFI. Park Series charcoal grill outside. Buffalo Mt trailhead 1/2 mile.

Guest favourite
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.

Guest favourite
A cozy living area includes a neutral-colored sofa with turquoise accent pillows and a soft area rug. Natural light enters through two windows with floral valances, illuminating the space. A small dining table with white chairs is visible in the background, enhancing comfort and functionality.
Tiny home in Forest Hills
4.86 out of 5 average rating, 21 reviews

Tiny Home w/Full Kitchen - Walk to Distillery

Little Cottage offers a comfortable space for a quick visit or a lingering stay to explore everything in the community from riding the Hatfield-McCoy Trails, fishing the Tug River, hiking to the West Virginia swing, or some peace and quiet in a safe and friendly neighborhood. Conveniently located near shopping, restaurants and just a few miles from a trailhead. Plan a visit to Pauley Hollow Distillery less than a half a mile from Little Cottage for real moonshine and Kentucky bourbon!

Guest favourite
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
4.92 out of 5 average rating, 232 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.

Top guest favourite
An aerial view of a ranch-style house with wood siding, surrounded by a large yard and featuring an in-ground pool. The property includes manicured landscaping and a private setting against a hillside, showcasing ample outdoor space for relaxation and activities.
Home in McCarr
4.98 out of 5 average rating, 131 reviews

God's Country

Property is a ranch style house with wood siding, nestled against a hillside with a private setting. This property offers a large yard with a in-ground pool as well as a large front porch. There are two patio areas in the back with a built in grill station and a fire-pit to enjoy on those cool evenings. The house boasts six bedrooms, open concept living room, kitchen, and dining room area with gas fireplace, and large family room.Please enter the correct number of guest

Top guest favourite
A wooden bench is positioned under a covered porch, complemented by a decorative welcome sign. Sunlight filters through the large windows, illuminating the outdoor dining area with a vibrant umbrella in the background, enhancing the inviting ambiance of the space.
Home in Delbarton
4.98 out of 5 average rating, 60 reviews

* Large Coded Access Garage Area Included*

Discover your perfect getaway! The Decked Out Den is a 3-bed, 2-bath 1400sqft home with a detached 30'x30' garage to protect your machines from the weather. Enjoy ample parking, a spacious deck, and a cozy living room. Conveniently located near multiple trail access points, it’s just a short ride to Matewan or Delbarton—no need to trailer. Explore Buffalo, Devil's Anse, or Rockhouse trail systems. Book now for an adventure-filled stay with all the comforts of home!

Superhost
A comfortable seating area features a dark sofa adorned with contrasting plaid pillows. A wall-mounted television is positioned above a decorative shelf displaying a plant and a welcome sign. Natural light enters through nearby windows partially covered by dark curtains.
Cabin in Williamson
4.68 out of 5 average rating, 53 reviews

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

Top guest favourite
A cabin entrance is framed by wooden steps leading to a covered porch with two rocking chairs. Behind, a rocky cliff provides a natural backdrop, and the ground is covered in gravel and scattered leaves.
Cabin in Delbarton
4.96 out of 5 average rating, 24 reviews

Cozy cabin, easy trail access

Relax with the whole family at this peaceful place to stay. Cross Mountain Cabins is nestled atop a mountain ridge overlooking a small creek perfect for an afternoon stroll. Buffalo and Devil Anse Trailheads within minutes of cabin allow quick access with no trailering. Come let us host you and enjoy what the area has to offer.

Popular amenities for Toler holiday rentals

  1. Airbnb
  2. United States
  3. Kentucky
  4. Pike County
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