Holiday rentals with outdoor seating in Frankfort

Chic Cabin w/ Trails, Hot Tub & Starry Nights

Privately nestled on over 5 wooded acres & intentionally curated for your stay. Gain access to quiet, immerse yourself in nature, support your rejuvenation, & to tap into your creative flow. Amenities include on-site hiking trail, artist work space, wood burning stove, covered porch, hammocks, outdoor dining, fire pit, moon garden, salt-water hot tub, & outdoor shower. Close to Beaver Lake & located along the Bourbon Trail, just minutes from Wild Turkey & Four Roses distilleries. (Note:18+only)

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.

Backyard Bourbon Retreat

Your family will be close to everything when you stay at this centrally-located place. This is a beautiful two bedroom two full bath home packed with a ton of amenities! Only minutes from several distilleries such as Buffalo Trace, Jim Beam, Woodford Reserve, Ancient Age and Four Roses just to name a few! There is a fully fenced in yard with a deck looking into a 1/4 acre landscaped backyard. Great for sitting back and relaxing with a Kentucky beverage. Welcome to the Backyard Bourbon Retreat!

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!)

Van Winkle's Secret/Speakeasy (Hidden Room)

If you like bourbon, you will LOVE this place. Perfect for families, friends, bourbon hunters, and bachelor/ettes! You will find a hidden speakeasy lounge if you look hard enough! There are 16 distilleries within 35 min, including Buffalo Trace (7 min). Wineries, breweries, bars, restaurants, and entertainment all within Frankfort! Featuring 3 king beds, a pullout couch, 2 full and 2 half baths. Gather on the patio or out by the fire. The large fenced in yard will give you plenty of privacy.

Lil Bit O' History on Main- Historic Downtown!

Built in 1867, with original deed of 1813, this beautiful piece of Frankfort's history has been fully restored! This cozy shotgun home offers magnificent views of the State Capital in front and of the Old Capital from the side! Located along the Bourbon Trail, it offers a short walk to BOM, local breweries, downtown coffee at Kentucky Coffee Tree, and all the shops of Broadway. The History Center is close, as is The Kentucky Military Museum. Buffalo Trace and Castle and Key are minutes away.

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.

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!

Capitol Walk/7min to Buffalo Trace

Enriched with history & tradition is where you will find Capitol Walk. 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!

The Loft - Cozy Retreat in Historic Downtown

Experience the magic of winter at The Loft your top-rated cozy escape just minutes from downtown. Wander to the Capitol, enjoy twinkling seasonal sights, and explore nearby Horse Country. Warm up in your private second-floor hideaway with a plush bed, comfy sofa, and modern touches. With parking at the door and a hygge-inspired vibe, The Loft is the perfect base for a stylish, snow-dusted Bourbon Trail getaway, inviting you to slow down, unwind, and savor the season.

Treetop Hideaway

Fully equipped apartment, only 5 blocks from the state Capitol in historic, tree-lined neighborhood. Kentucky Derby, Horse Park, and Bourbon Trail all close. Real pricing - no hidden fees! Downtown restaurants, entertainment, & distilleries are only minutes away by car or foot. Apartment includes everything for short-term or extended stays, including washer/dryer and fully-equipped kitchen. Separate building - totally separate entrance for privacy.

Limestone Landing - Cozy Luxury Retreat w/ HOT TUB

Limestone Landing is a modern, fully renovated, open space home in a country neighborhood setting. The home is the perfect retreat for your next getaway to Kentucky. Conveniently situated only a 1/4 mile from Castle and Key Distillery and 2 miles from Woodford Reserve. 1/2 mile from the highly rated restaurant and bourbon bar, The Stave. Indulge in the ultimate bourbon tasting experience, knowing that comfort awaits you at your cozy haven.