Vacation rentals with outdoor seating in Frankfort

Cottage On Crooked Creek

A tranquil cottage nestled in the lush countryside and situated right along the Bourbon Trail, this completely renovated rare find is located center of Lawrenceburg, Frankfort and Shelbyville and only 12 min to I-64. With five main bourbon distilleries just 30 min, local wineries within a stone's throw, Churchill Downs and Keeneland Racecourse equidistant and Taylorsville Lake nearby there is little left to be desired when staying here. This is the perfect spot to relax with family and friends.

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!)

The Stagg House on the Ky River

Nestled on the Kentucky River in Frankfort, KY, our peaceful retreat is surrounded by historic chestnut trees and wildlife like deer & cardinals. Just 5 miles from Buffalo Trace, 6.7 miles from Castle & Key, and 10 miles from Woodford Reserve and Whiskey Thief, it’s ideal for bourbon enthusiasts. Enjoy the river beach, backyard BBQs in summer, or cozy nights by the fireplace in winter—wood provided. Fully stocked kitchen, pet and family-friendly, with a secluded vibe yet close to the main road.

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.

★Escape & Relax ~ Breathtaking Creekside Getaway★

Escape the everyday hustle and bustle by immersing in the stunning glamping experience on a secluded creekside property. Enjoy solitude, romance or family time inspired by nature. Tucked away on our 13 acre residence, this spacious 16' tent offers a unique stay in a breathtaking ambiance. ✔ Queen Bed + 2 Full-Size Mattresses ✔ Outdoor Deck with Seating ✔ Bathtub + Separate Shower ✔ Composting Toilet ✔ Creek Access + Kayaks ✔ Cooking Station Learn more about this glamping haven below!

Sweet Hollow Farm

Sweet Hollow Farm is located near Taylorsville Lake. 30 miles from Louisville, 40 miles from Lexington and 25 from Bardstown. We have a small farm with a studio barn apartment. Private entrance with full bath. We also have a beautiful pool that we share with our guests. There is a horseshoe pit, fire pit and multiple outdoor seating areas. Kids and dogs welcome. We even have space for horses and boats. We can offer peace and quiet, a clear view of the stars and hummingbird theatrics.

Bourbon Trail Cabin on the Farm

Recognized by AirBnB as the “2021 Top New AirBnB in the State of KY”!Overlooking rolling hay fields, and surrounded by wooded farm land, this cabin features barn wood walls, hardwood floors, handcrafted bourbon barrel sink, king bed, leather sleeper sofa, and custom built kitchenette. Located on a working cattle farm, see cows, goats, a donkey and horse, & our pet free-range pig! In the heart of the Bourbon Trail in the home of Wild Turkey and Four Roses.

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.

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.