Vacation rentals in Paintsville

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.

175acreFarm *Paintsville Lake and *Red River Gorge

Welcome to Ghillie Dhu. Escape to our secluded Appalachian farm, where tranquility and nature await. Nestled in the rolling hills, our farm offers a private oasis with no neighbors in sight, allowing you to truly disconnect and unwind. Experience the star-filled night sky free from any light pollution, and fall asleep to the peaceful sounds of the countryside with nothing but the bullfrogs to disturb you. Explore our two stocked ponds, perfect for fishing or simply relaxing by the water's edge.

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.

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

Bee Still Tiny Home, Graham Estates, LLC

Take a step into our dreamy tiny home when the world is telling you to find a place to "bee still." The perfect destination for a romantic getaway, or a family vacation where the kids can make a fort in the loft. You will love this quiet, serene space located up a scenic driveway. The porch overlooks a small pond, and across the road you will find our small farm of goats and piggies. Take a walk around the property or enjoy all the adventures awaiting at Red River Gorge 35 minutes away.

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.

The Yellow House

Getaway on this 300+ (with 700+ available nearby) acre working farm. Explore pastures, woodlands, rock cliffs and beautiful vistas while looking for wildlife (hiking has some restrictions Sept to Dec) . Enjoy a picnic or evening fire listening to whip poor wills at the campground located on the property; or have a peaceful cup of coffee on the porch. Traveling with your horse /ATV, ask about available stall and trail access. Located between Paintsville, Yatesville and Grayson lakes.

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.

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.

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.

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.

“Historic Guest Suite | Private & Modern”

🌿 Welcome Welcome to the Patterson House — a clean, cozy, and comfortable home located in Paintsville. Whether you’re visiting family, working in the area, or just passing through, this space is designed to make your stay simple, relaxing, and stress-free. 💬 Our Goal We take pride in providing a clean, cozy, and reliable place to stay every time. Your comfort matters, and we want your visit to feel easy from check-in to check-out.