Holiday rentals 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.

Studio 1101

Second story one bedroom studio above small hair salon. Unique building conveniently located near historic downtown, major highways, restaurants and distilleries. Wi-Fi and on-site illuminated parking available as well. A window A/C unit (added 8/25) helps keep the 2nd story space cool during summer months. W/D svc available on stays over 5 days. The salon generally closes at 6 p.m. T-Th so there will be no traffic or noise after that time. The salon is also closed Sunday and Monday.

The Loft - Cozy Retreat in Historic Downtown

Experience the warmth and comfort of The Loft; your top-rated retreat just 8 minutes from downtown. Walk to the Capitol, explore nearby sights, and enjoy horse country close by. Relax in a cozy bed, unwind on a comfy couch, and enjoy modern updates in your private second-floor apartment. With parking at the door and a welcoming hygge vibe, it’s perfect for recharging. Just minutes from 13 distilleries, The Loft is your ideal base for exploring the Bourbon Trail in comfort and style.

The Crafty Bourbon Bungalow Apartment

The Crafty Bourbon Bungalow Apartment is located in the historic district of Frankfort just three blocks from the Capitol and within walking distance of downtown shops and restaurants. We are in the heart of horse and bourbon country with easy access to local distilleries and racetracks. The apartment has a private entrance, one parking space, two bedrooms with queen beds, one bath with claw tub/shower combo, kitchenette and an eating and sitting area.

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.