Holiday rentals in Pleasureville

The Log Cabin at StoneLedge

Please note the Log Cabin is a private home BUT the entire cabin is not avaliable for use when booking 4 guest or less. Nestled on an expansive 80 acre horse farm the log cabin is the perfect escape. Hike the 30+ acres of woods that boast a creek and waterfall. Relax on the cozy front porch while enjoying the sounds of nature. The Log Cabin is 10 minutes off of I71 exit 22. Less than 3 minutes to Ashbourne Farm & approximately 10 minutes to Hermitage Farm. ***PLEASE READ THE ENTIRE LISTING

On The Rocks

Ultimate in privacy, yet two minutes from downtown Frankfort! This cabin-style home (think Gatlinburg!) sits on three wooded acres. Long, rambling decks on three sides (one covered, one fully screened, one open air). Our adjacent farm surrounds the property, making it even more private. This home sits high on a bluff above downtown Frankfort & the Kentucky River (our farm borders on the river). Just three miles to Buffalo Trace Distillery (if you could fly, it's way closer than that!)

Lux Horse Farm * Pklball * Swim Spa * Sauna * Golf * Speakeasy

Escape to your own private 5 acre horse farm, surrounded by rolling hills and amazing views for a rare one-of-a-kind-getaway. This newly renovated 7-bed, 4 full bath estate blends luxury living with endless amenities to provide a Kentucky experience like no other. Enjoy the Golf and Pickleball Sports Lounge or slow down to sip and savor in our authentic Speakeasy. Unwind and relax however you would like! An ideal location where you are a short drive to Louisville, Frankfort, Lexington and more.

Bourbon Trail Country Getaway

Escape to the peaceful countryside and unwind in our restored farmhouse surrounded by rolling farmland. This secluded retreat with three gas fireplaces is ideal for romantic getaways, bourbon enthusiasts, or family-friendly stays. Whether you’re sipping morning coffee on the porch, gathering around the firepit, enjoying some friendly competition in the game barn, or exploring the nearby Bulleit Bourbon Distillery on the Bourbon Trail, you’ll find tranquility and adventure in equal measure.

Nelson Farms Bunkhouse

You’ll have plenty to enjoy country living at its best at this historic place in a picturesque setting. This is a 470 acre working Beef Cattle farm that is centered in the Golden Triangle of Louisville, Lexington and Cincinnati, one hour from each. We have 3 hook ups for campers and plenty of space for vehicles including horse trailers. Our Bunkhouse is on the Bourbon Trail with 6 distilleries within 25 miles. Enjoy hiking and exploring by day and quiet evenings at night by the firepit.

Beautiful Farm Stay on the bourbon trail!

This memorable place is anything but ordinary. Enjoy the picturesque views from the farmhouse of the pastures. Watch as the sheep and horses graze. On the hour you can hear the sound of church bells. When the wind is right, the smell of mash from local distilleries wafts through the air. Make one of a kind memories on our beautiful farm. Included in your stay are fresh farm eggs (when available), enough coffee, creamer, sugar for the first morning, and 6 bottles of water and farm tour.

Bourbon Trail Retreat | Game Room, Fire Pit & Pond

This beautiful 3250 sf log cabin is perfectly situated in the heart of the Bluegrass State, ready to be your base for all things Kentucky. Bourbon, horses, antiques, The Creation Museum, The Ark Encounter, Churchill Downs and so much more are all within a short drive. Or, who wants to go anywhere when you and your companions have all you need to spend quality time together on our 20 acre getaway. Walk the trails, enjoy the firepit or the deck overlooking the pond, lawn games and more.

The Bourbon Coop

The Bourbon Coop is arguably the best situated location on the Bourbon Trail! It is a convenient walk or golf cart ride to Whiskey Thief distillery across the street. Situated a quarter of a mile off interstate 64, in between Louisville and Lexington, with a 15 minute drive into the city of Frankfort. The cabin is located on a beautiful, scenic plot of land, shared by the friendly hosts, chickens, ducks and a couple of goats. This is a comfortable, quiet and quaint country experience!

Kentucky Bourbon Trail Estate: Hot Tub & Game Room

⭐⭐⭐⭐⭐ Superhost · 4.92 stars · Guest Favorite Trailside Country Haven is a 3-bedroom Kentucky countryside retreat sleeping up to 10, perfectly located on the Bourbon Trail in Shelby County. Hot tub, game room with arcade, fire pit, multiple decks & Starlink WiFi. 🥃 Minutes from Jeptha Creed, Four Roses, Woodford Reserve, Wild Turkey & Buffalo Trace. 🎮 Arcade · Shuffleboard · 65" Roku TV 🔥 Hot tub · Fire pit · Gas grill · Multiple decks 🏡 3BR · 5 beds · 2.5 baths · Sleeps 10

Jeptha Crest-Bourbon Trail, Hot Tub, Sauna, Dog OK

Jeptha Crest is a designer-built and thoughtfully decorated home, perfectly placed in the heart of the Bourbon Trail yet hidden among trees and nature views. Though centrally located, it feels like a private forest escape, offering rare privacy and calm. A spacious two-level deck, fire pit, hot tub, and sauna invite you outdoors, while inside, clean modern design blends seamlessly with warm, cozy comfort — a refined retreat created for slowing down and truly unwinding.

Cottage of Eden. Bourbon Trail Stay in Shelby Co.

Listen to the birds sing as the walkway guides you to your quaint cottage getaway. Take in nature, as you’re surrounded by trees, near our sweet chicken coop and a creek down from the deck - all while only 10min from town. Special touches were added of Kentucky Derby photos, books, kitchenware, Bourbon Trail glasses and bourbon barrel heads with local distilleries. The dining table top is even made of wood from Shelby County’s own Bulleit Distilling Company.

Quiet Downtown Maple Cottage Gem

Welcome to our charming Maple Cottage in the heart of a peaceful downtown neighborhood. This 3-bedroom, 1-bathroom home has undergone a complete remodel, ensuring a cozy and comfortable stay in Shelbyville. Whether you're here for a weekend getaway or an extended stay, this cottage offers all the amenities you need. The fully fenced backyard offers privacy and space for relaxation and smores over the fire pit. Your Shelbyville adventure begins here!