Vacation rentals in Jeffersonville

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Top-rated vacation rentals in Jeffersonville

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Guest favorite

Apartment in Mount Sterling

4.94 out of 5 average rating, 48 reviews

Historic 2-Bedroom Apartment in Downtown

Charming apartment in the historic Farmers National Bank building in downtown Mount Sterling. Recently renovated, the apartment provides the comfort and amenities of home, yet retains all of the character of the original building. Within walking distance of many great restaurants and if you’re in the mood to shop, stop in to Lily Aesthetics downstairs or take a stroll down Main Street to find a variety of great shopping opportunities. Located within 35 miles of Lexington and the Red River Gorge.

May 15 – 22

€ 116 per night

Guest favorite

Cabin in Stanton

4.97 out of 5 average rating, 31 reviews

Red Door Cabin Six

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!

Oct 10 – 17

€ 113 per night

Superhost

Cabin in Stanton

4.91 out of 5 average rating, 33 reviews

Red Door Cabin Two

Mar 29 – Apr 5

€ 113 per night

Superhost

Apartment in Clay City

4.82 out of 5 average rating, 38 reviews

Gran's Guest House RRG! Special Spring Rates!

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.

Jan 7 – 14

€ 107 per night

Guest favorite

Home in Mount Sterling

4.96 out of 5 average rating, 138 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!

Sep 15 – 22

€ 86 per night

Guest favorite

Loft in Mount Sterling

4.93 out of 5 average rating, 28 reviews

Downtown Loft Apartment, Relaxing Retreat

Loft upstairs apartment with one bedroom and full amenities. Kitchen, washer/dryer, and WiFi. Located in downtown Mt Sterling. Walking distances to local specialty, shops, and restaurants. One block away from Renee’s Bridal and Market Pavilion. Mt Sterling is situated 25 miles west of Morehead and 35 east of Lexington, KY. Great location to stay to enjoy the Red River Gorge/Natural Bridge State Resort Park which is 24 miles a way. Great location for creativity, shopping or adventure.

May 19 – 26

€ 94 per night

Guest favorite

Tiny home in Stanton

5.0 out of 5 average rating, 37 reviews

Tiny Cabin At The Pond

Situated on a hobby farm on Cane Creek Mountain, this tiny cabin is a 4 year dream in the making. We are pleased to offer it up for your getaway from the hustle and bustle of everyday life. The pond is stocked, and fishing poles are provided. We even provide treats for the donkeys, but don't believe their story of being starved, especially the little one! We're 20 minutes to Slade or Stanton and 25 to Mount Sterling if you need to make a supply run. We look forward to hosting you!

Jul 22 – 29

€ 132 per night

Guest favorite

Home in Winchester

4.91 out of 5 average rating, 672 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.

Jun 12 – 19

€ 62 per night

Guest favorite

Guesthouse in Winchester

4.98 out of 5 average rating, 174 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 now 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.

Dec 5 – 12

€ 78 per night

Guest favorite

Farm stay in Jeffersonville

5.0 out of 5 average rating, 5 reviews

Welcome to the Star Cottage!

Come enjoy your stay at the beautiful Rockin R Farm! This charming 3 bedroom cottage overlooks pastures full of beautiful green hills, spotted with a herd of rare and endangered Mountain Pleasure horses, including many mares and foals. You can sit on the front porch and enjoy your coffee while watching herds of gorgeous horses peacefully grazing. Or enjoy a cocktail while seeing some of our spectacular sunsets here on the Rockin R.

Apr 22 – 29

€ 201 per night

Guest favorite

Cabin in Stanton

4.94 out of 5 average rating, 18 reviews

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.

Mar 4 – 11

€ 180 per night

Guest favorite

Home in Stanton

4.92 out of 5 average rating, 134 reviews

RRG Climbers Choice Stay-Wifi- No cleaning fee

We'll have you feeling like a local in two days minimum and in a town so friendly you might just become one. Fully furnished duplex (SIDE B) is minutes drive from the best Red River Gorge hiking trails, climbing, Miguel's, Natural Bridge State Park, The Gorge Underground, Callie's Lake, La Cabana & Kroger. On the Scenic Byway in Stanton. Side A & B can be booked together if availability allows.

Jan 8 – 15

€ 89 per night