Vacation rentals in Prestonsburg

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Top-rated vacation rentals in Prestonsburg

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Top guest favorite

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

4.97 out of 5 average rating, 31 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

Top guest favorite

A porch area features two black chairs and a small wooden table, inviting relaxation outdoors. A decorative plant in a blue pot adds a touch of greenery, while the entrance to the guesthouse is adorned with a small diamond motif and an American flag.

Guesthouse in Blackey

5 out of 5 average rating, 46 reviews

An Appalachian Mountain Getaway. ATV friendly

Nestled in the mountains of Eastern Kentucky, this location offers stunning mountain views. It's ATV friendly, with secure and complimentary vehicle parking. A multitude of trails are available for riding, with walking paths on the property. Riding tours are also offered. The accommodation features a newly remodeled one full bed, a walk-in shower, and all the amenities, including a complete mini kitchen and a 32" TV. It's a peaceful and relaxing retreat after a day spent exploring the trails.

Top guest favorite

The compact kitchen area features modern shelving with a variety of kitchen essentials, including a microwave, coffee maker, and utensils. A wooden countertop provides workspace, while a sink is positioned beneath a welcoming sign. A bathroom area is visible in the background.

Tiny home in Pikeville

4.95 out of 5 average rating, 44 reviews

Modern Escape

Modern Escape at Harvey's Hideaway Haven is a contemporary retreat that offers all the comforts of home in a compact and stylish package. (160 sq. ft. of living space) At Harvey's Hideaway Haven, you'll be immersed in nature, surrounded by the beauty of the wilderness. While this offers a peaceful escape, please be aware that you may encounter local wildlife, including bugs, bees, and other creatures that share this natural setting. Located just 9 miles from PMC, Upike and the Expo center!

Guest favorite

The cabin's exterior is softly illuminated at twilight, featuring a welcoming entrance with colorful doors. A stone pathway leads to a cozy seating area surrounded by greenery and potted plants. The car parked in the foreground adds to the homey feel of the location.

Cabin in Prestonsburg

4.89 out of 5 average rating, 107 reviews

The Eagle's Rest Country Cabin

Welcome to the Eagle's Rest! This family & pet friendly cabin is nestled outside of Prestonsburg. Mountainous escapes of sunrises & sunsets w/access to a private 20-acre mountain for hiking & birdwatching. Enjoy plenty of 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/DirecTV & T-Mobile Int. Located near StoneCrest Golf Course, Jenny Wiley State Park, & Sugarcamp MtnTrails & Middle Creek Battlefl

Guest favorite

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

4.88 out of 5 average rating, 52 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.

Guest favorite

A cozy seating arrangement is presented with two light-toned sofas, complemented by decorative cushions. A round table is positioned between them, enhancing the living space. The room features soft lighting, a mirrored reflection of the bedroom area, and a door leading to another room.

Apartment in Stanville

5 out of 5 average rating, 9 reviews

Cozy Studio

Welcome to your perfect home away from home! This 1-bedroom, 1-bath rental is designed for comfort and convenience, featuring a fully equipped kitchen to prepare your favorite meals, an in-unit washer and dryer for easy laundry, and Wi-Fi and a TV for entertainment and relaxation. Enjoy a peaceful stay with the privacy of your own driveway, making parking hassle-free. Whether you’re here for work or leisure, this cozy space has everything you need for a stress-free and enjoyable stay.

Top guest favorite

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, 129 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.

Top guest favorite

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

4.97 out of 5 average rating, 33 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.

Top guest favorite

A rustic cabin features a welcoming wooden facade with multiple large windows. A covered front porch with yellow seating is visible, surrounded by lush greenery. The entrance is flanked by steps leading up from a gravel path, inviting guests into a serene natural setting.

Cabin in Campton

4.97 out of 5 average rating, 181 reviews

Private 12 Acre Escape - Hot Tub, Firepit, Arcade

12 acres of peace and quiet in Campton. You can wander the trails, kick back by the firepit, or just take in the forest views. Evenings are for porch sunsets, hot tub stargazing, and the sound of birds all around. Inside, there’s a vintage Ms. Pac-Man for a little throwback fun. We’re about 15 miles from Red River Gorge, but it feels like you’ve got the whole place to yourself—no close neighbors, no traffic, just dark skies and starry nights.

Top guest favorite

A well-maintained single-story home features a welcoming porch and steps leading to the entrance. The light-colored siding is complemented by maroon shutters. A pathway lined with gravel and plants enhances the outdoor space in a friendly neighborhood setting.

Home in Prestonsburg

5 out of 5 average rating, 22 reviews

6 minute walk to Starbucks.

IMPORTANT NOTE: Snow removal and salt application during the winter season is not provided. This will be the occupant's responsibility. ASK ABOUT LONG TERM RENTAL. 30 MINUTE DRIVE TO PIKEVILLE HOSPITAL. LESS THAN 10 MINUTE DRIVE TO HIGHLANDS ARH HOSPITAL IN PRESTONSBURG, KY. AAA property right in town, walk to Starbucks, super size grocery store and many restaurants. We are a 55 and older community.

Guest favorite

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.

Vacation home in Prestonsburg

4.98 out of 5 average rating, 159 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 favorite

The exterior of the blue cottage is showcased, featuring a covered front porch with a railing and an entry door. Surrounding the property, trees provide partial shade, while the landscaping includes a gravel area. A vehicle is parked nearby, contributing to a welcoming atmosphere.

Cabin in Davella

4.98 out of 5 average rating, 59 reviews

Blue Moon at Airport Cottages

Blue Moon is a featured cottage available at Big Sandy Regional Airport. Conveniently located close to Jenny Wiley State Park. Just a short distance from Inez, Paintsville and Prestonsburg. Take it easy at this unique and tranquil getaway. Enjoy the mountains of Eastern Kentucky with us and all things local 💙