Vacation rentals in Jeffersonville

4.88 out of 5 average rating, 69 reviews

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 Specials!

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.

4.98 out of 5 average rating, 319 reviews

A scenic view of a poolside deck captures the early morning sun rising over the mountains. A pair of Adirondack chairs are positioned nearby, beside a firepit. The serene landscape is featured with rolling hills and a layer of mist hovering in the valley.

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

A cozy bedroom features blue walls adorned with butterfly decor and soft lighting. A queen bed is dressed with a floral comforter and surrounded by an inviting area rug. A small couch and side table add to the room's charm, with doors leading to additional living spaces.

Home in Mount Sterling

4.83 out of 5 average rating, 217 reviews

THE DOLLY - Cozy, Bright Home in Historic Downtown

Hello, Dolly! This bright and cozy home in the heart of downtown Mt. Sterling provides comfort and convenience. With hundreds of unique artifacts and rare photos to discover, you will find peace, relaxation, and tons of Dolly-themed photo ops! In addition to WiFi and Roku TV, guests will enjoy a massive collection of Dolly Parton films, records, and books. A fully-themed kitchen, bedroom, dining room, and bathroom offer many fun Dolly touches. A place so cute, even Jolene wants to stay!

4.97 out of 5 average rating, 406 reviews

A rustic cabin is nestled among vibrant autumn trees, positioned above a serene pond. A small dock with two chairs is visible near the water's edge, inviting relaxation. The surrounding landscape features lush greenery and colorful foliage, enhancing the cabin's secluded feel.

Cabin in McKee

Mountain Dream Cabin -Fish Pond+Fenced Yard+Stalls

Escape to a peaceful cabin with a wraparound porch perfect for soaking in the beauty of nature. This pet-friendly retreat features a fenced yard and space for trailer parking, plus four horse stalls available upon request. Enjoy catch-and-release fishing in the stocked pond, or explore nearby attractions: 25 minutes to Berea’s historic downtown and Pinnacle Trails, and 30 minutes to Flat Lick Falls and Sheltowee Trace. Unwind, explore, and experience the charm of our small-town getaway!

5 out of 5 average rating, 88 reviews

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!

4.91 out of 5 average rating, 853 reviews

The entrance of the cottage features a wooden door framed by two windows, offering natural light. A decorative wreath adorns the door, and wall sconces provide additional illumination. The exterior showcases white siding with teal accents, complemented by a brick pathway leading to the door.

Home in Winchester

Cozy Cottage

Sweet little cottage within walking distance of historic downtown Winchester. Open floor plan, 500 square feet of coziness! Queen size bed, kitchen, living room, dining all in one place. We’re a working farm on the edge of the city limits in an older non-gentrified neighborhood. Surrounded by the Kentucky Horse Park, Keeneland, Rupp Arena, Fort Boonesboro, Red River Gorge and the Kentucky Bourbon Trail. Easy access to I-64, I-75, and Mountain Parkway - gateway to Appalachia.

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.

4.92 out of 5 average rating, 209 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!

4.99 out of 5 average rating, 154 reviews

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

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.

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.

4.91 out of 5 average rating, 107 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+. Must b 24 yrs or older to rent. Msg with questions!

Superhost

An aerial view of Skyview Cabin showcases its unique construction elevated on stilts above a wooded landscape. The roof slopes downward, and a spacious deck extends toward the tree line. Surrounding trees display a seasonal mix of bare branches and greenery.

4.85 out of 5 average rating, 105 reviews

Suspended SkyView Cabin Near RRG

Welcome to Skyview Cabin! A unique all wood construction suspended over a cliffside. What sets our cabin apart is its unique perch – suspended 30 feet up in the air, offering a truly elevated experience. The property is peacefully secluded, yet just a short 20 minute drive to Red River Gorge. Enjoy a nice soak in the hot tub after taking part in all the RRG has to offer : swimming, kayaking, boating, biking, fishing, golfing, hiking, caving, and rock climbing.

4.96 out of 5 average rating, 27 reviews

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.

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.