Holiday rentals in Pleasureville

Close to Buffalo Trace/Transpo available-Must See

Best place to stay on the Bourbon Trail FEATURED on HGTV! Swanky! Stunning! Spectacular! You'll be in a top-floor loft overlooking downtown Shelbyville and perfectly situated in the heart of the Bourbon Trail! Incredible place to stay for Derby, Keeneland, PGA or local weddings and events---if you can pry yourself away from here! We specialize in making your stay an over-the-top experience and are happy to arrange chauffeured transportation, private chef accommodations, and dinner reservations.

Close to Buffalo Trace •Hot Tub• Grill • Nature

Bourbon Hills Retreat is a newly renovated 4BR, 2.5BA farmhouse on 13 private acres with stunning hilltop views. View the hollers of KY while watching the deer cross the yard. Sleeps 8 comfortably. Enjoy the hot tub, porch rocking chairs, starry nights, and peaceful surroundings. Minutes from Buffalo Trace & Bulleit, horse tracks, wineries, and Bourbon Trail favorites. Centrally located between Louisville & Lexington—perfect for family getaways, couples, or group trips exploring Kentucky’s best!

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!)

Golf Sim•Karaoke•SpeakEZ•2 Hot Tubs•Sauna•MiniGolf

Welcome to Bottled in Bond by LIVE & TRAVEL HOMES! Where bourbon country meets play, wellness, and unforgettable stays. Enjoy a home theater, wellness area, golf simulator, mini golf, karaoke, fire pit, and plenty of space to gather, laugh, and unwind. Whether you’re teeing off, singing your favorite song, relaxing after a day on the Bourbon Trail, or sharing stories by the fire, this is your place to reconnect & make lasting memories. Minutes from Buffalo Trace & the heart of Bourbon Country.

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.

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

*NEW* hot tub-sauna-large pool-game room-speakeasy

Escape to comfort and style at Expression on the Rocks: A newly renovated 6BR, 4400 sq ft retreat in the heart of the Bourbon Trail. Set on 5 lush acres with scenic views of hills and wildlife, this home offers a hot tub, sauna, inground pool, firepit, speakeasy w/poker lounge, and gameroom. Perfect for group getaways-just minutes from Kentucky’s world-famous distilleries. Who needs to be the center of the universe when you can stay in the center of the Bourbon Trail? Book Now!

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.

LUX Farmhouse | HotTub | Firepit | GameRm | 5 Acre

Brand-new luxury farmhouse on 5 private acres in the heart of Kentucky bourbon country. This 4BR retreat sleeps 12 and is built for unforgettable group getaways, with a massive game room, full bar, pool table, shuffleboard, foosball, poker table, 85” TV, covered 6-person hot tub, huge firepit, outdoor games, and a fully stocked chef’s kitchen. Minutes from Buffalo Trace, Bulleit, and Jeptha Creed. Send us a message with any questions!