Vacation rentals in Prestonsburg

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Top-rated vacation rentals in Prestonsburg

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Guest favorite
Cabin in Prestonsburg
4.88 out of 5 average rating, 113 reviews

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.

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
4.8 out of 5 average rating, 158 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 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
4.98 out of 5 average rating, 40 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 favorite
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, 139 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 favorite
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, 65 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 favorite
A cozy bedroom features a spacious bed adorned with light linens and decorative pillows. Above the bed, a wooden sign displays the phrase 'Be still & know.' Large windows allow natural light to fill the room, creating a serene atmosphere accentuated by white walls and a chandelier.
Tiny home in Jackson
4.95 out of 5 average rating, 106 reviews

Bee Still Tiny Home, Graham Estates, LLC

Take a step into our dreamy tiny home when the world is telling you to find a place to "bee still." The perfect destination for a romantic getaway, or a family vacation where the kids can make a fort in the loft. You will love this quiet, serene space located up a scenic driveway. The porch overlooks a small pond, and across the road you will find our small farm of goats and piggies. Take a walk around the property or enjoy all the adventures awaiting at Red River Gorge 35 minutes away.

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, 137 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 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, 115 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.

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
4.98 out of 5 average rating, 204 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 spacious porch features natural wood flooring and sturdy railings, offering views of the lush greenery. Two comfortable wicker chairs are set against the railing, providing an inviting space to relax while enjoying the serene surroundings of the pond and trees.
Cabin in Rogers
5 out of 5 average rating, 99 reviews

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.

Guest favorite
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 Vest
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 favorite
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, 271 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.

Popular amenities for Prestonsburg vacation rentals

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