Holiday houses in Prestonsburg

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Top-rated holiday rentals in Prestonsburg

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

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Superhost

A comfortable bedroom is present, featuring a neatly made bed covered with a light quilt. A decorative pillow adds a touch of accent. Natural light enters through a window with blinds, and a stylish light fixture illuminates the room. A nightstand with a lamp is positioned beside the bed.

Home in Pikeville

4.82 out of 5 average rating, 149 reviews

Living The Dream

*If you book for 7 days or more, you will receive a 20% discount off your stay. Our home is perfect for your visit in Pikeville, especially for a large group. Enjoy the complete home with 3 bedrooms, 2 full baths, a complete kitchen with dishwasher, & washer/dryer. You'll enjoy a good nights sleep in a quiet space on high quality mattresses. We are located just down the street from a Food City. We have free WIFI & a Smart TV (NO CABLE TV). We’re a short 5 minute drive from downtown Pikeville.

Top 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

4.97 out of 5 average rating, 34 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

Guest favourite

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

4.96 out of 5 average rating, 47 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 favourite

The kitchen features a spacious island with four cushioned stools, modern pendant lighting, and a distinctive SMEG fridge. Clean countertops offer ample prep space, while stylish green tile backsplashes add a chic touch. The area is well-lit and flows seamlessly into the living space.

Apartment in Pikeville

4.93 out of 5 average rating, 133 reviews

Walk to dinner, UPIKE, hospital•3 Lux Bed• Balcony

Upstairs-The Eccentric Privy is the best of the best worlds. Retro, glam & quirky! You’ll obsess over the thought put into each room & even get some inspiration. Extra amenities include… Outdoor deck Quartz Countertops Luxury tile SMEG fridge Smart thermostat Bathroom Bluetooth speaker USB outlet in each room Soft close doors & drawers in kitchen & bathroom 550 TC cotton bed sheets and pillow covers Allergy defense, antimocrobial pillow protectors Tankless water heater for endless hot water

Guest favourite

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

4.88 out of 5 average rating, 109 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 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, 59 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

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, 130 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 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

4.97 out of 5 average rating, 35 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.

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, 163 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, 264 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.

Top Guest favourite

A spacious bedroom includes a large bed adorned with white and green bedding. A piece of wall art featuring trees hangs above the bed. A bedside table with a lamp and a soft area rug add comfort. Natural light enters through the window covered with dark curtains.

Home in Harold

4.98 out of 5 average rating, 116 reviews

Cozy & Charming between Pikeville/Prestonsburg

Quiet and peaceful location just off of US 23 highway. Centrally located between Pikeville and Prestonsburg. 10 mins from City of Pikeville and 15 minutes from City of Prestonsburg Minutes from shopping and restaurants. Beautiful lakes and parks close by.

Guest favourite

A grand facade of the home is showcased under a clear blue sky, featuring a large arched entrance framed by elegant landscaping. A decorative bronze fountain stands prominently in the foreground, surrounded by a neatly paved driveway that leads to the entrance.

Home in Prestonsburg

5 out of 5 average rating, 9 reviews

Mountain Manor Luxury Estate

Our fabulous Mountaintop get-away (now under new management) is nestled on nearly 2 acres atop Stonecrest Golf Course. This sprawling property is perfect for family gatherings, receptions, bonding retreats, and more – we’ve even had weddings!