Holiday houses in Eastern

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Top-rated holiday rentals in Eastern

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

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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
4.96 out of 5 average rating, 46 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

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Guest favourite
Apartment in McDowell
5.0 out of 5 average rating, 18 reviews

Tranquil 2-bedroom apartment

Consider this lovely apartment your home away from home while you visit McDowell. With queen beds in the 2 bedrooms and a cozy living room with a futon, there's plenty of space for guests to relax, including a front porch. Enjoy the beautiful bathtub in the bathroom and take advantage of amenities like heating, AC, Wi-Fi, and a washing machine. A welcoming retreat in the heart of the city, this apartment is a great place to call home base while you're away. We hope you enjoy your stay.

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Top Guest favourite
Cabin in Rogers
4.96 out of 5 average rating, 142 reviews

The Turtle • Pet friendly • Hot Tub • Romantic

The Turtle is a modern A-frame cabin with a private hot tub near Red River Gorge and Natural Bridge. Decorated with original folk art by Wolfe County artists, it offers forest views, an outdoor TV, fast Wi-Fi, and cozy comfort. Peaceful, pet-friendly, and close to hiking, climbing, and scenic trails, this secluded yet convenient getaway is perfect for couples or friends seeking a romantic or adventurous escape. The Turtle blends art, music, and nature into a relaxing Kentucky retreat.

ValueFamilyView

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
4.94 out of 5 average rating, 143 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.

ValueFamilyHospitality

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
4.93 out of 5 average rating, 138 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.

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Top Guest favourite
Home in Irvine
4.98 out of 5 average rating, 126 reviews

Premium A-Frame • Hot Tub • Sauna • Pond & Animals

Private 58-acre A-Frame retreat in the Kentucky Appalachians with mountain views, a stocked fishing pond, hot tub, infrared sauna, fire pit, games, and rare farm animals. Meet Suffolk Punch draft horses, a Highland cow and calf, and Thoroughbreds by request. No TV by design, just nature, stillness, connection, and a true farm-stay experience. Sleeps 7. Designed for families, couples and friends seeking nature, privacy and unforgettable memories.

ValueLocationComfort

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
4.97 out of 5 average rating, 216 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.

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Guest favourite
The cabin exterior showcases a wooden structure with large glass windows, allowing natural light to illuminate the interior. Surrounding foliage enhances the secluded feel, while a wooden deck extends from the entrance, leading to an outdoor space with a hot tub visible nearby.
Cabin in Stanton
4.95 out of 5 average rating, 402 reviews

Seclusion Cabin - Tower, Treehouse, Koi Pond

Seclusion is a completely custom, hand-crafted cabin complete with a treehouse room, koi pond, rocky landscape, observatory tower and more in an unbeatable location. This cabin is located just a mile or two off the Slade, KY exit on top of a ridge in Red River Gorge. Built by Paul Rhodes in his spare time, this passion project took over six years to complete and boasts a uniqueness unrivaled by other accommodations.

ValueFamilyAir conditioning

Top Guest favourite
A private hot tub is situated on a spacious deck, illuminated by soft blue lighting. Trees surround the area, providing a serene backdrop. The screened-in porch above is adorned with warm cafe lights, enhancing the cozy evening atmosphere.
Cabin in Wellington
4.96 out of 5 average rating, 114 reviews

Slow Motion Hideaway Cave Run Lake/RRG - hot tub!

Breathe deep. Slow down. Stay awhile. Slow Motion Hideaway is a cozy A-frame cabin tucked in Kentucky’s Daniel Boone National Forest, just minutes from Cave Run Lake and close to Red River Gorge. Hike, kayak, ride ATVs, or spend the day on the water—or curl up with a good book and never leave the cabin. A quiet place to reconnect—with the woods, with your people, or with yourself.

ValueFamilyBarbecue

Top Guest favourite
Cabin in Rogers
4.98 out of 5 average rating, 204 reviews

Romantic Cabin • Private Hot Tub • Red River Gorge

“Imagine an Ikea showroom with a beautiful wall of windows looking out into the woods” — Maggie ⭐️⭐️⭐️⭐️⭐️ Escape to The Outpost, a design-forward cabin tucked into six wooded acres in the foothills of Red River Gorge. Floor-to-ceiling windows frame the woods, while high ceilings and an open layout keep this cozy hideaway bright, calm, and connected to nature.

ValueFamilyAccess

Top Guest favourite
A geodesic Zome is perched on stilts, surrounded by trees. The structure features a welcoming entrance with a door framed by greenery. A pathway lined with stones leads towards the Zome, while decorative lights twinkle in the background.
Dome in Wolfe County
4.93 out of 5 average rating, 112 reviews

Unique Glamping Experience in our RRG "Zome!"

Reconnect with nature at this unforgettable escape. Nestled just outside the heart of the Red River Gorge, this property is certainly a step up from camping. With a full bath house, outdoor prep area, and so many other amenities, we’ve made certain that you will be comfortable and have everything you need and more for an amazing stay at the RRG.

ValueLocationQuiet

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
4.96 out of 5 average rating, 189 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.

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Popular amenities for Eastern holiday rentals