Holiday rentals in Jeffersonville

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Top-rated holiday rentals in Jeffersonville

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Cabin in Frenchburg

4.96 out of 5 average rating, 121 reviews

Shine On near Red River Gorge!

A cozy little getaway located at the entrance of Indian Creek Resort!! Keep it simple at this peaceful and centrally-located place. Amazing cabin located near Red River Gorge, Daniel Boone National Forest and Cave Run Lake. A Private Backwoods wonderland!! A short scenic drive(20-40 minutes) to everything the area has to offer. Centrally located between Kentucky's most desirable hiking trails. Forget your worries on the spacious back deck, relax and unwind in the hot tub. 1bed/1bath

Superhost

Cabin in Stanton

4.88 out of 5 average rating, 564 reviews

Hot Tub, WiFi, Netflix and Cable, Close to RRG!

Very secluded cabin in the mountains. Quiet and surrounded by woods. Huge backyard to walk your dogs! Nature walks, hiking and rock climbing are all just a short drive down the road to the famous Red River Gorge. Natural Bridge State Resort Park is only a 14 mile scenic drive. 7 person hot tub and all amenities included in your stay. A place to get away from the city, unwind and enjoy the company of those around you. Fresh mountain air, cozy moments to remember. Mountain Home is calling!

Guest favourite

Guest house in Stanton

4.98 out of 5 average rating, 268 reviews

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

Guest favourite

Home in Mount Sterling

4.88 out of 5 average rating, 185 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!

Guest favourite

Cabin in Mckee

4.97 out of 5 average rating, 307 reviews

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!

Superhost

Cabin in Frenchburg

4.89 out of 5 average rating, 132 reviews

Modern Woodland Cabin w/ Hot Tub

The perfect place to escape and wake up amongst trees or spend a weekend w/friends! Welcome to Tall Stüga - "Pine Cabin". Our incredibly modern, Scandinavian-themed cabin! You're located on the Sheltowee Trace, minutes from Cave Run Lake and only 25 country miles from Red River Gorge. :) There is public access to hiking trails, boat docks, horse camps, local golf course, parks & more. Plus, you'll be close to numerous quaint little towns, state forests, antique stores & local markets.

Guest favourite

Tiny home in Powell County

4.96 out of 5 average rating, 256 reviews

Hot Tub! Tiny Hūs Retreat in the Woods

Enjoy your own slice of the Red River Gorge in our unique, cozy tiny house. Soak in a brand new hot tub after enjoying the beauty of “The Gorge,” just a short 15 min drive to the Natural Bridge! Feel immersed in the outdoors with the sounds of nature, tons of natural light, and gentle rain on a metal roof. Roast marshmallows at the fire pit, grill food at the charcoal grill, then take a nap in the 2-person hammock before retiring in the *tiny* loft on a comfortable queen-sized bed.

Guest favourite

Home in Stanton

4.95 out of 5 average rating, 140 reviews

The Retreat, 30 min from RRG/Natural Bridge

Modern 3 Bedroom 2 Bath on 11.5 acres roughly 20 miles from Red River Gorge. Entire house has been renovated. Starlink Internet, Electric fireplace, Smart TVs in all bedrooms/living room, Pinball Machine, and Ceiling fans in all bedrooms/living room. Fire-pit area with porch swing, chairs, bench for food, picnic table, and string lights for entertaining. The house sits on 11.5 acres, guests are welcome to walk the property. Large wrap around driveway for easy arrival/departure

Guest favourite

Cabin in Stanton

5 out of 5 average rating, 238 reviews

Rocky Flatts Cabin Pets Welcome No cleaning fee

Adorable two bedroom with sleeper sofa and cot capable of sleeping 6, one bath, located on working 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.

Guest favourite

Home in Winchester

4.9 out of 5 average rating, 744 reviews

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 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.

Guest favourite

Guest house in Winchester

4.98 out of 5 average rating, 208 reviews

Escape and unwind in the country

Relax and unwind in the country! Close to Lexington, Red River Gorge, Pilot Knob and Natural Bridge with easy access to the Mountain Parkway. We do have Wi-Fi. Pets are welcome but we request that dogs are either crated or not left unattended. There is a $25 pet cleaning fee. Our guest house has a fully equipped kitchen, washer/dryer, queen size Sleep Number Bed, queen size sleeper sofa, and patio with gas grill. An air mattress is available by request.

Guest favourite

Cabin in Stanton

4.94 out of 5 average rating, 314 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.