Holiday rentals in Jeffersonville

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Top-rated holiday rentals in Jeffersonville

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Guest favourite
A cozy cabin interior features warm wood paneling and an open layout. A sleek kitchen area is equipped with modern appliances, while a flat-screen television is mounted on the wall. A patterned area rug anchors the seating area, which is complemented by natural lighting from nearby windows.
Cabin in Stanton
4.92 out of 5 average rating, 110 reviews

Red Door Cabin Two

6 unique cozy and newly built cabins located in the beautiful and serene Red River Gorge area. Family owned and operated, Behind the Door Property Consulting. Less than 15 minutes for Miguels & Nada Tunnel, 45 minutes from Lexington, KY, and easy access to local Kroger. Each property has a dedicated outdoor grill and there are 3 shared fire pits on property. These are cabins in RRG and each cabin is equipped with internet, but cell service and internet can be spotty as is the whole area!

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, 210 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
A treehouse nestled among tall trees features multiple levels, wooden stairs, and a sturdy deck. Surrounding foliage and a forest floor covered in leaves add to the serene atmosphere. Comfortable seating areas are located at the base, inviting relaxation in the natural setting.
Treehouse in Stanton
4.87 out of 5 average rating, 434 reviews

Serene Ravine Private RRG Treehouse

Stay in a custom-built treehouse nestled in the heart of the Red River Gorge forest on private land—perfect for family getaways, romantic escapes, or friend trips! Explore great views, built along a peaceful stream, and the calming sounds of nature. Step outside to a nearby trailhead leading to Gray’s Arch and more. Just 15 mins from local favorites like Miguel’s Pizza, coffee shops, and mini golf! Availability is limited - so be sure to lock in your summer vacation before it's gone!

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, 116 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.

Guest favourite
Cabin in Jeffersonville
4.91 out of 5 average rating, 34 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, 109 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
The exterior of a manufactured home is visible, featuring a wooden deck and several steps leading up to the entrance. An American flag is displayed on a nearby tree. Lush green grass surrounds the structure, with trees providing shade.
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 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, 120 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
A modest bunkhouse is positioned on a sprawling green lawn, surrounded by gentle hills. A covered front porch invites relaxation, while a gravel driveway provides access. The landscape features a mix of trees and bushes, enhancing the rural charm of the setting.
Home in Jeffersonville
4.97 out of 5 average rating, 34 reviews

Welcome to the Bunkhouse!

The bunkhouse boasts 3 large bedrooms, two offer queen beds, while the master has a king. Two full baths and an additional sectional couch in the living room guarantee you plenty of room to spread out and enjoy your stay! Enjoy a peaceful stay on a working rare breed horse farm surrounded by large herds of both young and old horses as well as other farm animals. Gorgeous sunsets are as common as the gorgeous equines spotting the 70 acre farm.

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, 397 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.

Popular amenities for Jeffersonville holiday rentals