Family-friendly holiday rentals in Frankfort

Bourbon Trail*River Views*Hot Tub*Sauna*EVSE*WiFi

Welcome to River Whisper. The remodeled riverfront house offers the perfect blend of organic modern decor and unparalleled comfort. Experience luxury with top-of-the-line features, a hot tub, and a barrel sauna, all overlooking the beautiful Kentucky River. Located in the heart of Bourbon Trail, with easy access to many renowned distilleries, including Buffalo Trace and Woodford Reserve. Explore historic downtown Frankfort, Cove Spring Park, river boat tours, kayaking, fishing, hiking and more.

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!)

Bourbon Trail: Caboose on the Farm

Nestled under the shadows of 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 bunkbeds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

River Row Bungalow

Come visit the River Row District. Located in the heart of Downtown Frankfort. Within walking distance to shops, dining, bourbon, live music and the Capitol Building! Discover what Frankfort has to offer during the day. Come home to relax in the hot tub and enjoy a fire in the yard. Have your morning coffee and relax in the swing under the covered porch, while listening to the church bells. Sleeps 8 with two king beds, 1 queen bed and two twin beds in a loft space within the queen bedroom.

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.

Capitol Walk/7min to Buffalo Trace

Walking distance to the State Capitol, this historic home has recently undergone renovations & no expense was spared. Featuring 3 bedrooms & 2.5 bathrooms, guests are able to experience life like a local with all the modern-day amenities. Walking distance to Downtown Frankfort & only a 7-mile drive to Buffalo Trace and 15 minutes to Castle & Key Distillery. Guests can even walk to Rebecca Ruth Candy or Andy's Bakery! Property features on-street parking.

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.

Downtown Frankfort, Bourbon Trail Distilleries

Bourbon Sunshine is a warm, inviting Craftsman home in downtown Frankfort with a welcoming front porch.The 4 bedrooms and 2 baths, it comfortably sleeps 10 and offers a relaxing front porch to unwind. Just 2 miles from Buffalo Trace Distillery and steps from downtown eateries, the State Capitol, and local treats like Rebecca Ruth Candy, it’s the perfect blend of cozy charm and comfort while you call this place home as you explore the Bourbon Trail.

Limestone Landing - Cozy Luxury Retreat w/ HOT TUB

Limestone Landing is a modern, peaceful home, thoughtfully designed with comfort and style in mind. This cozy haven offers a relaxing place to unwind after a day of exploring bourbon country. Just minutes from Castle and Key and Woodford Reserve and only ½ mile from the highly rated restaurant and bourbon bar, The Stave. Whether you’re here for tastings, scenic drives, or quiet evenings in, Limestone Landing puts you right where you want to be!

The Loft - Cozy Retreat in Historic Downtown

The Loft isn't just a place to stay; it's the feeling of finally slowing down. This cozy, light-filled retreat invites you to wake up easy, explore bourbon country, wander historic Frankfort, and return to a space that feels instantly like home. Thoughtfully designed with warm textures, modern comforts, and a peaceful atmosphere, it's the perfect escape for couples, solo travelers, and weekend adventurers seeking a memorable Kentucky getaway.

Hot Tub > 3 King Beds > 7 mins to Buffalo Trace

Welcome to BOURBON HOLLOW! 🦬 Buffalo Trace - 3.5 miles/7 minutes 🔑 Castle & Key - 8 miles/15 minutes Whiskey Thief - 9 miles/15 minutes 🥃 Woodford Reserve - 14.2 miles/21 minutes 🦃 Wild Turkey - 15.2 miles/23 minutes 🌹 Four Roses - 18 miles/23 minutes 🥃 Bulleit - 15.4 miles/24 minutes 🎩 Jeptha Creed - 25.6 miles/28 minutes Lexington Area Distilleries - 31 miles/35 minutes Louisville Area Distilleries - 52 miles/52 minutes

Blue's Bourbon Bungalow

A bourbon lover’s paradise. Located minutes from the worlds best Bourbon distilleries and within walking distance of several dining establishments. Enjoy walking the grounds of the state capital and touring several of Kentucky’s historical museums. Centrally located between the thriving cities Lexington and Louisville, Frankfort is the perfect home base to explore everything Kentucky has to offer.