Holiday houses in Pilgrim

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Top-rated holiday rentals in Pilgrim

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

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Top Guest favourite
The exterior of a modern building is shown, featuring a dark metal facade with wood accents. Several doors with small square windows are visible, accompanied by outdoor seating. A wooden deck extends along the front, enhancing the inviting entrance.
Apartment in Lenore
5 out of 5 average rating, 23 reviews

Hidden Jewell Studio Suite #2 - 2BD/1BA on Outlaws

Cozy 4 private unit suite-style retreat sleeps 15 w/ full bathrooms, kitchenettes & comfy temperpedic beds. Located right on the Outlaws - no trailering - that connect to HMT, just minutes from the historic Dingess Tunnel - "America's Bloodiest Tunnel" Enjoy fishing at Laurel Lake that's stocked w/ fish. Outdoors unwind by the firepit, grill & picnic area under the stars. Large parking lot for trucks & trailers. A serene escape w/ a touch of history & lots of adventure *Tablet available to rent

Guest favourite
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
5 out of 5 average rating, 61 reviews

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

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
4.82 out of 5 average rating, 38 reviews

New Paint & Flooring - Cozy Creekside Tiny Home

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!

Top Guest favourite
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, 135 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.

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.
Apartment in Pikeville
4.91 out of 5 average rating, 243 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
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, 113 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 favourite
A two-story cabin structure is shown with a sloped roof and multiple balconies. The exterior highlights natural wood and a combination of materials, while the clear blue sky enhances the scene. The surrounding landscape is not visible, focusing attention on the architectural details.
Cabin in Delbarton
4.93 out of 5 average rating, 15 reviews

Cabin 6 @ THE ROCK 3 Bedroom 5 Beds Sleeps 9

THE ROCK located at Buffalo Mountain Point puts you in the heart of the town of Delbarton, WV . After a long day on the trails you can enjoy a short ride back to relax outback by the cozy fire-pit, chill on the entry level porch while overlooking the peaceful streams and landscape of the mountains or escape from it all on the basement level patio (hot tubs coming soon) . The location, flexibility and convenience of these Newly Built Cabins will not disappoint.

Superhost
Home in Inez
5 out of 5 average rating, 5 reviews

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.

Guest favourite
A cabin exterior is illuminated at night, showcasing a wooden porch with two rocking chairs. Large glass doors offer glimpses into the interior, while warm lights enhance the inviting ambiance of the entryway. Steps lead up from a gravel path to the porch.
Cabin in Logan
4.92 out of 5 average rating, 181 reviews

Riverfront cabin and mini campground

Relax with the whole family at this beautiful Cabin. A very peaceful place to stay. Sits on the Guyandotte River that's great for kayaking. Very close to the Hatfield McCoy Bear Wallow trailhead. Unload your ATV and hit the trail. Restaurant on site and also very close to a car wash. If you need a place to stay for the holidays while visiting family, this is the place for you! Just a couple of miles from Chief Logan State Park .

Guest favourite
The cabin with a wooden exterior is accessed by a staircase leading to a covered porch. Surrounding the cabin, a gravel driveway provides ample parking space, while trees line the area, enhancing the natural setting.
Cabin in Williamson
4.88 out of 5 average rating, 25 reviews

Cozy 2-bedroom Cabin with free parking

Country Charm is a newly built cabin located in Naugatuck, WV. This cabin has 2 bedrooms with queen size beds, full bath, full kitchen, living room, washer and drier, 2 larger porches, gas grill, fire pit, cable and WIFI. We’re 1 mile from Panther Mart (gas station and hot bar) Within 12 miles of HMT access. Conveniently close to several outlaw trails along with public hunting land in WV and KY.

Guest favourite
A vibrant mural depicting mountains and a sun creates a striking backdrop. A cozy seating area is featured in front, with a teal couch contrasted against a wooden floor. A stylish lamp adds a touch of warmth to the space.
Holiday home in Prestonsburg
4.98 out of 5 average rating, 169 reviews

The Burg

Enjoy local venues, The MAC, Planetarium, Jenny Wiley Lake, 1620 Distilling Company, hiking, biking, wildlife, local artisans and crafts. Home to Loretta Lynn's, Butcher Holler. Civil War History. Close to downtown shopping, walking distance to dining, coffee shops, and bakery. There are 2 rather short flights of stairs to access this unit.

Top Guest favourite
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
4.98 out of 5 average rating, 270 reviews

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.

Popular amenities for Pilgrim holiday rentals

  1. Airbnb
  2. United States
  3. Kentucky
  4. Martin County
  5. Pilgrim