Holiday 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.

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

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.

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.

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.

*Cozy 2BR Apartment | Walk to Downtown Paintsville

🌿 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.

Modern Cozy Cabin Near RRG, Muir

Welcome to Red Tail Rest, a peaceful, modern retreat in the heart of Red River Gorge. This newly built, bright, and secluded getaway offers a perfect blend of comfort and nature. Nestled among the trees and overlooking a serene pond, this cabin is half a mile from Muir Valley, making it an unbeatable location for rock climbers, hikers, and nature lovers.

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.

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.