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Holiday rentals 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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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.
Flat in Pikeville
4.94 out of 5 average rating, 124 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
4.89 out of 5 average rating, 106 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 cozy living area features a teal sofa and a patterned armchair. A circular wooden coffee table is centered on a colorful area rug. Two windows allow natural light, while floral artwork is displayed on the wall above the sofa.
Flat in Pikeville
4.93 out of 5 average rating, 189 reviews

Big Blue House Apt 1

We are located in downtown Pikeville, within a very short walk to Pikeville Medical Center and UPike. Enjoy the conveniences of a full kitchen and a quiet area where you can expect a peaceful night's sleep on a quality mattress. There is one queen bed and also a twin rollout bed. Street parking is available in front of the house only. (Please don’t park in the driveway or block it.) We have door code entry so there's no need to hassle with keys. We have a smartTV (no cable) and free Wifi.

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, 57 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

Guest favourite
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.
Flat in Stanville
5 out of 5 average rating, 8 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.

Guest favourite
An outdoor seating area is visible through large glass doors, featuring two comfortable chairs and a hot tub. A ceiling fan rotates above, and a mounted TV is situated on the wooden wall, with lush greenery seen in the background.
Cabin in Wellington
4.91 out of 5 average rating, 170 reviews

BreatheInnLuxury @ CaveRunLake

Kick back and relax in this calm, stylish space. Nothing says relax like Breathe Inn. This cabin in the woods is your respite in a completely private setting. Breath Inn has a Fiber Optic Internet w/WiFi, full kitchen, indoor/outdoor fireplaces, fire pit, covered patio, hot tub, outdoor TV. Slide the wall of windows off the primary bath to a private deck with hot tub, outdoor seating area and TV. Enjoy the private views of Daniel Boone National Forest. Breathe, Relax, Repeat.....

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, 124 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 open living area features wooden paneling and modern amenities. A comfortable black lounge chair sits alongside a beige futon. The kitchen area includes wooden cabinets, a microwave, and a refrigerator. Bright ceiling lights illuminate the space, creating a cozy ambiance.
Cabin in Pikeville
5 out of 5 average rating, 19 reviews

Backwoods Bungalow

Backwoods Bungalow at Harvey's Hideaway Haven is a rustic retreat designed to bring you closer to nature while offering the comforts of modern living. 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, frogs and other creatures that share this natural setting. Located just 9 miles from Pikeville Medical Center, Upike and The Appalachian Wireless arena.

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
4.92 out of 5 average rating, 128 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.

Top guest favourite
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
4.98 out of 5 average rating, 174 reviews

12 Acre Secluded Escape - Hot Tub, Firepit, Grill

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.

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
4.99 out of 5 average rating, 156 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.

Superhost
A restful bedroom features a full-sized bed dressed in soft linens and a vibrant throw. Natural light floods the space through a window with blinds. A small desk and chair are present, alongside a mirror reflecting the room's bright, airy feel.
Flat in Pikeville
4.88 out of 5 average rating, 16 reviews

Convenient & Cozy | Free Laundry, Wi-Fi, & Parking

Welcome to your home away from home - the perfect blend of comfort, convenience, and style for the traveling professional or those seeking a long-term stay. Our newly furnished one-bedroom apartment offers a tranquil retreat with all the modern amenities you need to live, work, and relax.

Popular amenities for Prestonsburg holiday rentals

Quick stats about holiday rentals in Prestonsburg

  • Total holiday rentals

    Explore 10 holiday rentals in Prestonsburg

  • Nightly prices starting at

    Prestonsburg holiday rentals start at £59 per night before taxes and fees

  • Verified guest reviews

    Over 460 verified reviews to help you choose

  • Wifi availability

    10 of Prestonsburg holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Prestonsburg rentals

  • 5 Average rating

    Prestonsburg stays are highly rated by guests – averaging 5 out of 5!

  1. Airbnb
  2. United States
  3. Kentucky
  4. Floyd County
  5. Prestonsburg