Holiday houses in Jeffersonville

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Top-rated holiday rentals in Jeffersonville

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Top Guest favourite
A panoramic view captures the sunrise over rolling hills and valleys, with the sun illuminating the horizon. Mist blankets the lower areas, adding a soft texture to the landscape. The sky is painted with gentle hues of orange, pink, and blue, enhancing the scenic beauty.
Guest suite in Stanton
4.98 out of 5 average rating, 213 reviews

Harriet’s Hideaway: Amazing Mountaintop Sunrises

A rustic guest suite in the lower level of a log home. This open floor design features live edge tables, a large 75” screen tv with internet based channels, great wifi & an amazing view of the mountains & sunrises right outside your door! Your private deck has comfortable seating & a hot tub provided for your comfort. A Blackstone gas griddle is yours to use. A firepit with wood is provided! *Hosts do live upstairs, but the suite is sound insulated and noise from below has never been heard.

Guest favourite
The exterior of a spacious two-story home is depicted, featuring a white brick façade and wooden accents. A covered porch with steps leads to the entrance. Surrounding greenery includes trees and a well-maintained lawn, creating an inviting outdoor space.
Home in Stanton
4.97 out of 5 average rating, 117 reviews

Maple Grove at Red River Gorge/Hot tub/Arcade!

Escape to our 8+ acre retreat featuring a remodeled 3000 sq ft home with 5 bedrooms and 3 baths, accommodating up to 10 guests. Indulge in a gourmet kitchen, leather furniture, private hot tub, and arcade room. Stay connected with 300mb internet and Roku streaming. Outdoor amenities include EV charging, firewood, basketball, cornhole, and kids’ bikes. Relax in the ‘hammock hideaway’ or on the covered porches. Where we ensure your stay is unforgettable, prioritizing comfort and relaxation.

Top Guest favourite
Cabin in Jeffersonville
4.92 out of 5 average rating, 36 reviews

Fireflies & Fables, our cozy Red River Gorge cabin

Located on 2 acres, escape with your family or friends to our secluded, pet friendly Red River Gorge cabin where you’ll wake up every morning to the sounds of nature. You can start your day with coffee or a book on the peaceful screened in porch. Take a walk up the hill for views of the valley. Find an afternoon hike to see the natural arches in the area, and wind down with a board game or s’mores by the fire. Whatever your adventure, we hope you'll make lasting memories in our cabin!

Top Guest favourite
A wooden cabin is perched on a bluff, surrounded by vibrant autumn foliage. The structure features a welcoming porch with multiple windows, showcasing the natural beauty of the Appalachian Mountains during fall.
Cabin in Stanton
4.92 out of 5 average rating, 119 reviews

Cabin -40 acres, Hot Tub, 3-Sided Porch, Rec Room

Near the Natural Bridge, Hollerwood ATVs, & RRG! Get away from the hustle & bustle of life & reconnect w/ nature! Deep in the forest, u will discover a beautiful cabin overlooking a bluff in the magical Appalachian Mtns. Add a rec room, 3-sided porch w/ a pair of 6’ porch swings, 2 electric grills, hot tub, fire pit, small target range (+ much more) & you may never want to leave! 4 bedrooms but can sleep 16+. 10 miles to Natural Bridge. 24 yrs. or older to rent. Msg us with questions!!

Top Guest favourite
The kitchen features a large central island with a dark finish, complemented by light granite countertops. Bright, white cabinetry surrounds the space, enhanced by overhead pendant lighting. Stainless steel appliances, including a refrigerator and microwave, provide modern convenience amid an open layout.
Home in Mount Sterling
5 out of 5 average rating, 111 reviews

High Street Hideaway home atmosphere for relaxing

High Street Hideaway, relax away from the city in a spacious well appointed home atmosphere. Large back deck for relaxing and dining. No need to park on the street and walk a flight of stairs! Private parking with 4-5 steps up to deck and back door! *Access to Lexington 30-45 minutes away via Interstate 64. * 45 minute drive to the natural beauty of Red River Gorge for hiking/ climbing *30 min to Cave Run Lake * Three blocks to local shops, eateries, and town festivals!

Guest favourite
A charming entrance to a mobile home is seen, featuring a wooden staircase that leads up to the door. Lush greenery surrounds the property, including a prominent bush. An American flag flutters gently, adding a welcoming touch to the outdoor space.
Home in Stanton
4.93 out of 5 average rating, 203 reviews

The Towner

Escape to The Towner—your perfect home base for Red River Gorge adventures. Enjoy the rare combination of small-town convenience and easy access to Kentucky’s top outdoor destinations. Walk to restaurants, shops, and groceries, then spend your days hiking, climbing, kayaking, zip-lining, and exploring the Gorge just minutes away. Thoughtfully appointed with high-speed WiFi and all the comforts of home, The Towner is ideal for couples, families, and extended stays alike. ✨🏡🌄

Guest favourite
A modern kitchen features stainless steel appliances, including a spacious refrigerator and a gas range. Light-colored cabinetry contrasts with the decorative tiled backsplash. The wood ceiling enhances the inviting atmosphere, while track lighting illuminates the workspace.
Cabin in Stanton
4.91 out of 5 average rating, 245 reviews

The Cabin/Fully Fenced for Pets/15 miles to RRG

Slightly off the beaten path our cabin is nestled on 2 acres of land with a fully fenced in yard making it perfect for all your furbabies. Start your day with coffee on the front porch in our rocking chairs. After a long day on the hiking trails come relax in our hot tub or sit by the fire pit out front. We are about 15 miles from Red River Gorge, less than 10 miles to Stanton and about 50 miles to Lexington. Need to escape from the world? This property is perfect for you!

Top Guest favourite
A charming cabin is illuminated at night beside a stocked fishing pond. Water gently cascades from a fountain, creating a serene atmosphere. The surrounding landscape features trees and an open area, enhancing the sense of tranquility under the starry sky.
Tiny home in Stanton
4.99 out of 5 average rating, 183 reviews

Tiny Cabin At The Pond

Welcome to peace and quiet! If seclusion is what you're searching for, then you have found the place! Located on a hobby farm beside of a stocked fishing pond, it's as much of a destination as it is an accommodation. The closest neighbors are 3 friendly donkeys that love to greet guests at the fence for attention and ear rubs. Fishing poles and donkey treats are provided to round out your stay. We're 20 scenic minutes to Slade or Stanton and 25 to Mount Sterling.

Top Guest favourite
A cozy living area features a comfortable gray sofa paired with a rustic wooden side table. A small potted plant adds a touch of greenery, while a stylish lamp provides warm lighting. Nature-themed artwork adorns the walls, enhancing the space's welcoming ambiance.
Cabin in Stanton
5 out of 5 average rating, 121 reviews

Climbers Red River Gorge Getaway-Starlink

We'll have you feeling like a local in two days minimum and in a town so friendly you might just become one. One of a kind tiny home perfect for a weekend Red River Gorge getaway. Minutes drive from the best Red River Gorge hiking trails, climbing, Miguel's, Natural Bridge State Park, Hollerwood, Daniel Boone Backcountry Byway, The Gorge Underground, Callie's Lake, La Cabana & Kroger. Ample parking for multiple vehicles, or truck with trailer/sxs or crawlers.

Top Guest favourite
The cabin is nestled amongst lush trees, featuring a wooden deck that extends from the front. Large glass windows allow natural light to fill the interior while showcasing the surrounding nature. The driveway slopes gently upward towards the entrance.
Cabin in Slade
4.97 out of 5 average rating, 157 reviews

Maple Point - Dream Cabin in RRG

Welcome to Maple Point, an immaculate 1 bedroom + 1 bath cabin located in the heart of Red River Gorge. Completed in 2024, this property was thoughtfully created by a builder and designer to provide guests with a comfortable and memorable space to enjoy this region of Kentucky. Whether you are looking for a central base from which to explore, a quiet getaway where you can relax, or an inspiring space to work, we would love to have you come stay.

Top Guest favourite
A rustic cabin is set against a backdrop of a colorful sunset, showcasing its wooden exterior and a red metal roof. Surrounding the cabin, a fire pit is framed by seating made of tree stumps, creating an inviting outdoor space for gatherings.
Cabin in Stanton
4.98 out of 5 average rating, 170 reviews

Briar Patch Cabin-RRG | Fire Pit | Sunset | Wi-Fi

Located along the outskirts of the Red River Gorge Scenic Byway, The Briar Patch is perfectly situated to host travelers who are seeking both privacy and convenience. This cabin was thoughtfully designed to host anywhere from 1 to 6 people without making guests feel too cramped or in a space that’s too large to feel comfortable. Its rustic interior creates the perfect mood for this dreamy mountaintop vacation home.

Guest favourite
The cabin is nestled among vibrant autumn trees, with a large wooden deck extending from its front. A pathway leads to the entrance, which is framed by fallen leaves. The warm hues of the surroundings provide a serene and cozy retreat atmosphere.
Cabin in Frenchburg
4.92 out of 5 average rating, 122 reviews

Hygge Nock at Lush Hollow

Nestled perfectly on a ridge of our 40-acre property, minutes from Cave Run Lake and 25 miles from Red River Gorge, this Scandinavian-themed cabin is the perfect ridge-top retreat. Enjoy nearby hiking, boating, and golfing. Relax with a hot tub, pellet grill, and cozy fire pits. Explore quaint towns, state forests, and local markets. Your ideal super cozy, secluded getaway awaits!

Popular amenities for Jeffersonville holiday rentals