Holiday houses in Jeffersonville

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Top-rated holiday rentals in Jeffersonville

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Top Guest favourite

The spacious living area features a wooden interior with large windows allowing natural light. A comfortable dark leather sofa is arranged around a central coffee table. An entertainment area includes a TV and a circular mirror, while a door leads to one of the bedrooms.

Cabin in Jeffersonville

Endless View Cabin Rental

Endless View Cabin is conveniently located in the Red River Gorge/Natural Bridge area. It is a new construction (970 sq. feet of open floor plan). Bedroom 1 includes 1 queen size bed, dresser, hi-chest, nightstand and 55"TV. Bedroom 2 boosts a huge 4 adult queen size, Minnesota pine bunk bed with dresser. This cabin is dog friendly, loaded with board games for the family, has an outdoor fire pit, amazing views, quiet and secluded which allows for a great getaway for you and your friends/family.

5.0 out of 5 average rating, 30 reviews

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

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. Please msg us with questions!!

4.92 out of 5 average rating, 122 reviews

Guest favourite

An open living space features polished wood flooring and neutral walls. A circular coffee table sits at the center, surrounded by a cozy seating area. Bar stools line a kitchen counter, and glass doors lead to a deck, framed by checkered drapes for a rustic charm.

Apartment in Clay City

Gran's Guest House RRG! Early Fall Deals!

Located less than 20 minutes from the Red River Gorge and less than 5 minutes from the Kentucky Dragway is “Gran’s Guest House,” which has a farmhouse style that is practical, simple, and rustic, yet also embraces modern comforts that create a look that feels both cozy and stylish. Also only minutes away from the hidden treasure of Pilot Knob, a hiking overlook a hiking overlook considered to be the prominence upon which Daniel Boone first looked out over the Bluegrass region of Kentucky.

4.9 out of 5 average rating, 100 reviews

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

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.

4.96 out of 5 average rating, 120 reviews

Top Guest favourite

A spacious deck overlooks a lush green valley with rolling hills blanketed in morning fog. A circular hot tub is positioned on the deck, providing a tranquil view of the mountains in the distance. The scene is illuminated by soft sunlight.

Guesthouse in Stanton

Robbie’s Rest: Amazing Mountaintop Sunrises

2020 new unit with nice deck, wonderful mountain scape with amazing sunrises from your deck or the deck of the main house where host lives. 8 acres that sit where the rolling hills meet the mountains overlooking the Daniel Boone Forest. 35 miles from Lexington, you will enjoy the peace & quiet of the beautiful mountains. Minutes away from the trails, waterfalls & attractions of Natural Bridge State Park & the Red River Gorge! We hope you will visit us soon! *Sunrise is not always visible

4.98 out of 5 average rating, 381 reviews

Top Guest favourite

Home in Irvine

Pauline's Paradise

Welcome to Pauline's Paradise! You can enjoy a quiet and relaxing stay in our 2 bedroom home, with an adjustable King bed in one and twin beds in the other. You'll find a full kitchen, washer/dryer, wifi and Roku TV. We welcome well behaved pets. Handicapped entrance ramp. We're 25 min. away from Natural Bridge, Sky Bridge, Red River Gorge, hiking, underground kayaking and more. We're less than an hour from Lexington. We ask that you refrain from smoking inside during your stay.

4.99 out of 5 average rating, 145 reviews

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

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!

5.0 out of 5 average rating, 115 reviews

Guest favourite

Villa in Stanton

Red River Gorge. Indoor Pool. Game room. Pets.

Nestled in the quiet town of Stanton, Kentucky; 10-15 minutes away from all that Red River Gorge has to offer. 45 min to Lexington. Our house is whimsical and spacious. Perfect for families! We have a huge kitchen to cook a meal and relax by the fire pit in our private courtyard that overlooks the mountains. Also our Private pool is available March-Nov. Pet friendly (3 pet max) with a fully fenced in back yard. Please add pets to the reservation and pay the pet fee.

4.95 out of 5 average rating, 138 reviews

Superhost

A cozy cabin exterior surrounded by lush greenery, showcasing a well-maintained pathway leading to a seating area with a charcoal grill. Sunlight filters through the trees, highlighting the wooden structure and inviting atmosphere of nature.

Cabin in Powell County

Cozy Woodland Cabin -20 Min to Red River Gorge

Tucked away in the rolling Bluegrass hills, Elk Track Trail Cabin is a peaceful, secluded escape into nature — just a scenic 20–25 minute drive to world-class hiking at Red River Gorge and Natural Bridge State Resort Park. Follow a picturesque country drive to our cabin, where you’ll feel immersed in the woods while still enjoying the comforts of home. It’s the perfect balance of cabin comfort and that nostalgic “camping under the stars” feeling.

4.84 out of 5 average rating, 171 reviews

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

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.

4.97 out of 5 average rating, 38 reviews

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

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.

4.98 out of 5 average rating, 180 reviews

Top Guest favourite

Home in Clay City

Branch of Delight Getaway (The Front Porch)

Welcome to The Front Porch, a peaceful getaway in the foothills of Eastern Kentucky Near The amazing Red River Gorge and 1.4 miles from the Mountain Parkway, this cozy retreat offers both adventure and tranquility. Enjoy the surrounding forest views from the spacious porch, relax in the clean, comfortable living space, or unwind in the large yard. Country charm and comfort await at The Front Porch.

5.0 out of 5 average rating, 23 reviews