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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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
4.94 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

Superhost
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, 105 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.
Apartment 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, 55 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, 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, 18 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.

Top Guest favourite
The cottage stands nestled among trees, with a welcoming exterior illuminated by soft lighting at dusk. A well-kept walkway leads to double glass doors framed by inviting outdoor seating areas, creating an accessible entry point to the home.
Place to stay in Williamson
4.99 out of 5 average rating, 103 reviews

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.

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.

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.

Guest favourite
A charming cabin exterior is presented, featuring rustic wooden siding and a dark metal roof. A spacious front porch is accessible by steps, flanked by sturdy wooden railings. Surrounding grassy areas are visible, contributing to the natural setting of the cabin.
Cabin in Leburn
4.91 out of 5 average rating, 102 reviews

Deer Run Cabin (1) near Mine Made Adventure Park

A cabin located on private property next to ATV Training Center at the Mine Made Adventure park in Knott Co, Ky. This is the perfect weekend getaway with access to over a 1,000 miles of ATV and UTV trails. You will be able to experience all the beauty located in the mountains of Eastern Kentucky.

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, 253 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, 103 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.

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 $139 NZD per night before taxes and fees

  • Verified guest reviews

    Over 460 verified reviews to help you choose

  • Wi-Fi availability

    10 of Prestonsburg holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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