Holiday houses in Frankfort

Bourbon Trail: Caboose on the Farm

Nestled under the shadows of elm trees on a working cattle farm, The Southern x525 Caboose is now resting in the heart of the Bourbon Trail. Maintaining the industrial feel of an authentic caboose, while bringing in the warmth of handcrafted woodwork design, the Caboose on the Farm creates a unique experience like no other! Queen bed, twin bunk-beds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

The Cottage at Seldom Scene Farm - Bourbon Trail

SELF CHECK-IN, CLEAN, PRIVATE OASIS. Restored log home on gorgeous 273 acre farm along the KY RIVER. Serene & natural setting, close to several popular BOURBON TRAIL sites & horse farms. 10 MIN to WOODFORD RESERVE and CASTLE & KEY distilleries. 8 MIN to STAVE Restaurant & Bourbon Bar. Scenic horse farms (ASHFORD, AIRDRIE, WINSTAR). Convenient to KEENELAND, KY HORSE PARK, Versailles, Midway, Frankfort, Lexington, Louisville! Hike, bike, fish, wildlife, sheep, goats, chickens, stars & campfires.

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!)

Wilkinson's Wheated Oasis/ 1.3 Mi to Buffalo Trace

Wake up & smell the mash! Located just steps away from Buffalo Trace Distillery. Enriched with history & tradition is where you will find Wilkinson. This historic home has recently undergone renovations & no expense was spared. Guests will enjoy the walkability to Downtown Frankfort & many of the local attractions. Featuring 2 bedrooms & 2 baths, guests are able to experience life like a local with all the modern-day amenities. We are also only a 7.2-mile drive to Castle & Key Distillery.

The Loft - Cozy Retreat in Historic Downtown

Experience the warmth and charm of The Loft your top-rated fall retreat just 8 minutes from downtown. Stroll to the Capitol, see the autumn sights, and take in Horse Country nearby. Snuggle into a cozy bed, curl up on the couch, and enjoy modern touches in your private second-floor hideaway. With parking at the door and a hygge-inspired vibe, it’s perfect for crisp days and cozy nights. Just minutes from 13 distilleries, The Loft is your ideal base for a stylish Bourbon Trail escape.

Bing’s Downtown Guest Suite on Main

Make your home away from home at this centrally-located guest suite encompassing the entire second floor of the historic Bing’s Building in the center of downtown Frankfort, Kentucky! Historic downtown guest suite with modern amenities located in the heart of the capital city. Within blocks of great dining, shopping, entertainment, and historic sites. A short distance to Buffalo Trace and other popular distilleries, Keeneland racetrack, bluegrass horse country and much more!

Relax in the hot tub w/a view of the River!

Welcome to the Kentucky River Bourbon Cabin! Relax and rejuvenate in this cozy cabin nestled in a wooded setting & on the edge of the Kentucky River! Here you will find peace and serenity in nature with an upfront view of the water. Secluded and private yet still close to stores, restaurants and many tourist attractions such as major distilleries and wineries. Four Roses, Wild Turkey, Woodford Reserve and Buffalo Trace are just a short drive away.

Tiny Home with Huge Charm near the Elkhorn Creek

Just minutes from downtown Frankfort, this place is a little peaceful country getaway with a lot to offer! It’s nestled on a quiet street with great access to the beautiful Elkhorn Creek! If you’re into Bourbon tours, Horses, canoeing/kayaking/fishing, or Natural and Historical sites, this place is a great location in the middle of a lot to see and do! The tiny house has a small kitchen and bath as well as a yard and private patio and grill to enjoy!

Historic Loft in Frankfort Entertainment District

Experience the charm of a newly renovated 2-story loft in the Historic St. Claire Entertainment District of Frankfort, KY. Immerse yourself in the best of Kentucky, with convenient access to world renowned distilleries like Buffalo Trace and Woodford Reserve or catch the excitement of live thoroughbred racing at Keeneland Racetrack, just a short drive away in Lexington, KY. This special place is close to everything, making it easy to plan your visit.