Vacation rentals in Pilgrim

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Top-rated vacation rentals in Pilgrim

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Top guest favorite

A cozy living room is captured, featuring comfortable seating arrangements with a mix of neutral-toned sofas. A wooden coffee table stands centrally, accompanied by a decorative plant. A flat-screen TV is mounted on a wooden panel wall, enhancing the room's warmth.

Apartment in Delbarton

Welcome Y'all, Bring 'em all!

Bring the whole family, You get both apartments that connect. With this spacious 5 Bedrooms, 2 kitchens, 2 bathrooms, 2 laundry, plus 3 foldout twin beds is plenty of room for the whole family to spread out like jelly. We have a covered picnic area right out front with fire pit and grill. If you want to play in the creek or fish there is also a gazebo overlooking the creek. Trail 14 is straight across the road for all you trail riding adventures. We are close to Dollar Store and gas stations.

4.97 out of 5 average rating, 34 reviews

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

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!

4.98 out of 5 average rating, 46 reviews

Superhost

A single-story home is depicted from the front, featuring a welcoming porch with wooden steps. Large windows are adorned with dark shutters, allowing natural light inside. Surrounding greenery complements the exterior, and a gentle hillside is visible in the background.

Home in Williamson

Lil’ Owls Hideout

Located in Chattaroy, WV., Outside of Williamson, WV. 25 Mins from Matewan, WV. We are about 4.4 miles from the Buffalo Mountain Trail Head, access to Buffalo Moutain Trail 10 (WV Swing Overlook) is about 3.5 Miles away & Trail 12 about 3 Miles. About 2 Miles from Outlaw trails. Access to Devil Anse & Rockhouse Trails. The closest gas station is less than 3 miles away, who sells Hatfield & McCoy Trail passes. We are less than 5 Miles away from Shopping, Restaurants, & additional Gas Stations.

4.86 out of 5 average rating, 29 reviews

Guest favorite

A ranch-style house is set within a landscaped yard, featuring a welcoming sign at the entrance. Large windows on either side of the front door provide natural light, while the structure showcases a mix of wood and white siding under a sloped metal roof.

Home in Sprigg

3 Bedroom- 2 Full Bath Cozy home

Relax with the whole family or all your friends. Ranch style house located next to miles of OUTLAW Trails. Sleeps 8, 3 Bedrooms & 2 full baths and sofa bed. Fully stocked Kitchen. Laundry room. Spacious outdoor living with beautiful view of creek for fishing. HUGE private parking 5-6 trucks & trailers. 12 miles from the Historic Dingess Tunnel. Williamson, WV 15 miles -both Buffalo Mt Trails Delbarton, WV 9 miles to Hatfield McCoy Trails Dollar General, Gas Station, Pizza Rest. - .5 miles

4.96 out of 5 average rating, 23 reviews

Top guest favorite

A custom hanging bed is framed by a nature mural featuring tall trees, creating a serene ambiance. Soft bedding and decorative pillows add comfort. A sliding glass door leads to a private deck with seating, allowing for views of the lush surroundings.

Home in Inez

Luxury Creekside Cottage

Come soak up nature and get away from the hustle and bustle, check the completely remodeled cottage in downtown Inez, Ky The vacation rental features a luxurious interior, a spacious deck, and awe-inspiring views of the mountainous landscape. Spend your days walking the trails, hiking or riding ATV’s through the mountains. For a more relaxing adventure, take a short ride for the best elk viewing in the state. Sleeps 8 guests; 2 bedrooms; 1 Bathroom; https://www.airbnb.com/slink/VNxk38u6

5.0 out of 5 average rating, 76 reviews

Guest favorite

A single-story home is shown with a welcoming front porch supported by wooden posts. Two chairs are positioned on the porch, overlooking a grassy area surrounded by trees. Large windows provide natural light to the interior, enhancing the home's connection to the outdoors.

Home in Williamson

The Coal Miners Daughter

We would love to welcome you to our home in the mountains! Come enjoy a thrill seeking adventure then relax in the tranquility of your private home. Located at 717 Ruth Trace. Near Delbarton WV and 14mi town of Williamson WV. Trail riders can ride directly from the house to Buffalo Mountain Trails. Trail 14 is 7mi and 9mi to the trail head. Outlaws trails 1mi from home. Other info: spacious parking, 3bd home,2bd Queen,1bd dbl bunks(full bottom/twin tops) full kitchen,wifi,pet friendly :)

4.87 out of 5 average rating, 47 reviews

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

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.

4.98 out of 5 average rating, 127 reviews

Top guest favorite

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

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

4.97 out of 5 average rating, 148 reviews

Top guest favorite

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

* 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!

4.98 out of 5 average rating, 84 reviews

Guest favorite

Home in Inez

The Mountain Magnolia *Hot tub on private deck*

Step into bold industrial‑modern style with warm, comfortable furnishings that make relaxing effortless. This cozy home is packed with amenities! Featuring a private back deck complete with a steaming hot tub, charcoal grill, and outdoor sectional couch and chairs, perfect for unwinding under the trees. Designed for style and comfort, it’s an ideal retreat for couples, families, friends, or anyone craving a mountain getaway in a peaceful setting.

5.0 out of 5 average rating, 16 reviews

Guest favorite

The mansion is embraced by lush greenery, situated on a gently sloping landscape. A winding driveway leads to the property, which features multiple roof lines and a combination of stone and siding exteriors. Surrounding trees enhance the secluded feel of this tranquil retreat.

Home in Blaine

Hidden Acres Escape: A Bluegrass Retreat

Escape to our hidden gem tucked among the rolling hills of Blaine, KY. This secluded estate spans 200 scenic acres, offering solitude for those who crave true peace. Immerse yourself in nature’s beauty, unwind in the indoor pool, and bask in the luxury of a sprawling mansion. Whether you’re exploring miles of trails or savoring quiet moments overlooking lush vistas, discover an unforgettable sanctuary where nature and comfort unite.

4.82 out of 5 average rating, 147 reviews

Top guest favorite

The living area showcases a wood-paneled interior with a dining table and chairs adjacent to two cozy sofas. A television is positioned for easy viewing, and various decorative items, including mounted wildlife, are displayed on the walls and shelves, creating a rustic atmosphere.

Cabin in Louisa

Workman's Wildlife Haven

Vacation cabin (800 SF), secluded on 300 acre farm, hiking trails, wildlife viewing, 3 fishing ponds, 2 picnic areas, great scenery located in hills of eastern Kentucky. Fully furnished with wood burning fireplace, 1 bunk bed, 1 Queen Size bed/mattress, (sleeps 4). Nightly.

4.98 out of 5 average rating, 295 reviews