Holiday rentals in Jeffersonville

The Towner

Conveniently located to some of the best spots Eastern Ky has to offer, and yet, The Towner still has the small town country charm that has come to be expected of the Red River Gorge area. Guaranteed clean and comfortable!! Perfect for extended stays or short “getaways”. Located within city limits, The Towner is perfect for those who like adventure with the convenience of the city. High Speed WiFi, within walking distance of groceries and Restaurants, yet only 8 miles to Slade Welcome Center.

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.

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

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!

Guest Fav • Quiet & Romantic • Hot Tub • Fire Pit

Lil Red cabin is about 30-45 minutes from Red River Gorge, Natural Bridge, Underground Kayak and Cave Run Lake. Whether hiking, a wedding, romantic weekend or just getting away, Lil Red is the place! The cabin has been a favorite for visitors to the area for many years. Some of the favorite features are the year-round hot tub, large back deck, charming living room with gas fireplace to sit and read a book, play board games or watch the Smart TV. Come stay and relax in Lil' Red.

The Bluff on Amos Amazing Views!

This unique place has a style all its own. Centrally located between Red River Gorge and Cave Run Lake. Enjoy a hike at the gorge or a day at the lake. Come back enjoy soaking in the hot tub and take in the views!!! This spacious one bedroom one bath with tub/ shower is the perfect place for a getaway. It is equipped with full size appliances and everything you need to prepare a meal. The outdoor fire pit and charcoal grill are perfect for any outdoor cooking and relaxing!!!

Rocky Flatts Cabin Pets Welcome No cleaning fee

Adorable two bedroom with new mattress on sleeper sofa and cot capable of sleeping 6, one bath, located on a farm. Lots of wildlife. Beautiful country scenery. Located ten minutes from Natural Bridge State Park and the Red river gorge and Hollerwood ATV Park. Lot of room to park vehicles and atv's. Just sit on porch or in hot tub and relax. No 4x4 vehicle needed for access to cabin. Please clean up after your pets in the yard. We have supplies for pet clean up on porch.

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.

Cliffside Romantic Retreat LOVE

Fall in love at the unique and serene "Tis So Sweet Cliffside Cabin". The space is designed for a lovers retreat with luxuries of a spa bathroom, massage chair, fire table, recliner seat hot tub, and much more! This newly built cabin is peacefully secluded, yet still only a few miles away from the Natural Bridge State Park, Red River Gorge, Daniel Boone National Forest, underground kayaking, zip lines, rock climbing, swimming, delicious food and many other local attractions.

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.

Red River Unit 4 - 12 miles to Natural Bridge Park

<b>20% OFF FOR A WEEK! 30% OFF FOR 28 DAY STAYS! STAY 30 DAYS OR MORE AND PAY NO TAXES! BEST VALUE FOR RED RIVER GORGE! CLIMBERS AND HIKERS WELCOME! 2 SEPERATE BEDROOMS </b> 12 miles to RRG, right next to Kroger. Easy access, no need for 4x4, its right in town! - Duplex right side - Central A/C and heat. - washer/dryer/gas stove - Fiber wifi - 4k Roku TV - Off street parking, private driveway fits 2 to 3 vehicles. PLEASE READ HOUSE RULES FOR PETS.

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.