Holiday houses in Paintsville

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Top-rated holiday rentals in Paintsville

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

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Guest favourite

Cabin in Prestonsburg

4.88 out of 5 average rating, 117 reviews

The Eagle's Rest Country Cabin

Welcome to The Eagle's Rest! This family & pet friendly cabin is nestled just outside of Prestonsburg. Mountainous escapes of sunrises & sunsets. Enjoy family time w/a game room featuring a bar, billiard table, & dart board. Garage w/fire pit for entertaining or a small RV/Camper! Smart-Tv’s w/YouTubeTV & T-Mobile Int. Located near StoneCrest Golf Course. Put on your hiking boots for Jenny Wiley State Park, & Sugarcamp Mtn.Trails & Middle Creek Battlefield. Mountainous air & bird watching await.

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Guest favourite

The exterior of a wooden home is showcased, featuring a covered front porch with steps leading up to it. A gravel pathway and a welcoming sign are visible, surrounded by greenery. Large windows allow natural light into the space.

Cabin in Martin

4.96 out of 5 average rating, 46 reviews

Cecelia Ann Tiny Home 1/1 Quiet

Kick back and relax in this calm, stylish space. Quiet area Boho vibes, home was completed in November 2023 all new furnishings, complete kitchen, inside washer and dryer. All appliances, Keurig coffee pot for either single cup or entire pot. Covered front porch, off street parking. Close to several area hospitals, 16 miles to Pikeville and Appalachian Wireless Arena. Close to riding trails for 4 wheelers or side by sides. Less than 2 hours from casino, little over hour away from Red River Gorg

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Top Guest favourite

A charming cabin is set amid lush greenery, featuring a rustic wooden exterior and a slanted metal roof. Surrounding trees provide a natural backdrop, and a spacious lawn invites outdoor relaxation.

Cabin in Catlettsburg

4.99 out of 5 average rating, 275 reviews

The Cozy Cabin

Our "Cozy Cabin" getaway is located in a peaceful country setting. A creek & hillside is located behind the cabin. Relax on our 2 porches and enjoy the view of our field with horses grazing and deer passing thru. There is a fire pit, gas grill & small shelter house with swing for your outside enjoyment. All the amenities for a relaxing stay close to Yatesville Lake (18 miles), Rush Off-Road Park (13 miles) & Giovanni's Pizza (5 miles). Tristate area KY/WV/OH can be in all within 30 minutes.

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Guest favourite

A wooden interior features a spacious bed dressed with a white coverlet and decorative pillows. A classic rocking chair is positioned nearby, with warm lighting provided by overhead fixtures. A window allows natural light to illuminate the wood-paneled walls.

Cabin in Johnson County

4.9 out of 5 average rating, 60 reviews

The Daisy Cabin

Nestled in the hills and overlooking the serene creek, the Daisy Cabin provides the perfect escape from the hustle and bustle of everyday life. Loft space available for guests with sleeping bags. Step onto the cozy porch and breathe in the crisp, fresh mountain air as you listen to the gentle sounds of nature surrounding you. Wake up refreshed and ready to explore the wonders of the campground, from hiking trails to fishing spots, or simply bask in the tranquility of your surroundings.

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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

4.94 out of 5 average rating, 142 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.

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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, 124 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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Top Guest favourite

The exterior of a charming home is framed by a large tree and well-maintained shrubs. The house features a combination of brick and siding along with a welcoming yellow front door. A grassy lawn complements the overall inviting appearance.

Home in Paintsville

4.98 out of 5 average rating, 44 reviews

The Whitt House

A classic charmer, The Whitt House exudes character and is sure to make you feel right at home! With three bedrooms, a loft sporting a comfy futon, family room, living room, and fenced back yard, The Whitt House has room for the whole family to spread out and enjoy your time in Paintsville. Centrally located in a wonderful, people and dog-friendly neighborhood, the home is within walking distance to downtown and is perfect for enjoying all that Paintsville has to offer.

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Guest favourite

A wooden cabin is visible, featuring a red exterior and a covered porch with multiple seating options. The surrounding area is lush with green grass and forested hills in the background. A gravel pathway leads to a carport where a vehicle is parked.

Cabin in Salyersville

4.88 out of 5 average rating, 34 reviews

The Bear Cabin

Enjoy the peacefulness and privacy of a 2 bedroom + loft wooden cabin, with all the modern amenities, surrounded by 180 acres of forest. Explore the wilderness, do bird watching or just relax on the porch listening to the birds singing and the rustling of the creek. Or use the cabin as a base to explore the rich heritage and the natural beauty of the Appalachians. The location has easy access and it's also a short drive away from the city shops and restaurants.

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Guest favourite

A charming cabin is set against a lush, green backdrop, featuring a red roof and stone-accented front porch. The porch is lined with wooden railings and includes a seating area. An American flag waves gently in front of a grassy lawn, inviting guests to enjoy the outdoors.

Cabin in Hagerhill

4.93 out of 5 average rating, 138 reviews

Spacious 3 bedroom cabin with hot tub

Located in Paintsville, Kentucky. Gather around the wood fireplace and enjoy a game of pool. There are 2 smart tv's to binge your favorite shows on. Or unplug and and take in the sights on the wrap around porch with a good book. Enjoy the outdoor kitchen and firepit, then hop in the 8-person hot tub. located just 5 minutes from hiking trails, Paintsville lake state park and golf course, and local eateries . Walmart is conveniently only 8 minutes away.

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Guest favourite

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

4.83 out of 5 average rating, 145 reviews

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.

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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

4.96 out of 5 average rating, 188 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.

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Guest favourite

A charming cabin exterior is presented, featuring rustic wooden siding and a dark metal roof. A spacious front porch is accessible by steps, flanked by sturdy wooden railings. Surrounding grassy areas are visible, contributing to the natural setting of the cabin.

Cabin in Vest

4.91 out of 5 average rating, 103 reviews

Deer Run Cabin (1) near Mine Made Adventure Park

A cabin located on private property next to ATV Training Center at the Mine Made Adventure park in Knott Co, Ky. This is the perfect weekend getaway with access to over a 1,000 miles of ATV and UTV trails. You will be able to experience all the beauty located in the mountains of Eastern Kentucky.

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