Vacation rentals with a fireplace in Shelby County

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.

Countryside On the Bourbon Trail, 22 Quiet Acres

Welcome to Sea Glass Farm. 1900's restored farmhouse with tons of charm! Full access to 22 acres with beautiful hilltop sunsets. In the heart of The Bourbon Trail, the scenery and wildlife will not disappoint. The location is perfect for a rural getaway or relaxing stop on your Bourbon Trail experience. Minutes from shopping and restaurants; situated between I-64 and The Bluegrass Parkway. This place has been a dream of ours and it will soon be in your dreams as well. Hosted by the owner!

Cabin with spectacular views, creek, & hot tub

Located on beautiful Brashears Creek in the heart of Bourbon Country, this loft style cedar cabin makes a great central location to visit some local distilleries and wineries. It is also a great place to stay for anyone who might be in the area for a horse show or interested in antique shopping along Shelbyville's historical Main Street. My personal favorite thing to do at the cabin is enjoy the creek. The water level fluctuates significantly depending on the amount of rainfall received.

Your Kentucky Home Away From Home

Lovely, renovated Patio Home features 2 bedrooms and 2 full baths – one with a low-entrance shower and one with a full tub. This Open Floor Plan has 1st Floor Entry, front-door parking and 36” doors, making it easily accessible. This home is fully furnished throughout, including a full kitchen with all appliances, dishes, drinkware and silverware, washer and dryer, wall-mounted flat-screen television, tasteful art, linens, towels and more. This is your home away from home!

Cottage of Eden. Bourbon Trail Stay in Shelby Co.

Listen to the birds sing as the walkway guides you to your quaint cottage getaway. Take in nature, as you’re surrounded by trees, near our sweet chicken coop and a creek that flows down from the deck - all while only 10min from town. Special touches were added of Kentucky Derby photos, books, kitchenware, Bourbon Trail glasses and bourbon barrel heads with local distilleries. The dining table top is even made of wood from Shelby County’s own Bulleit Distilling Company.

Arcade | Fishing Pond | Cabin on Farm | Slps 12+

Last Minute Availability Alert! The Rec Farm: Your Ultimate Derby Destination! This stunning retreat, although not new to the Bluegrass Stays Collection, has just opened up for last-second bookings. Situated a mere 10 minutes from I-64, it offers unparalleled convenience for those seeking easy access to the Churchill Downs excitement. Sleeps 13 along with amenities like an arcade, hot tub, and fire pit. Secure your spot now and make your Derby dreams a reality!

Kamp Kessa at Cedar Fire Farm: A Nature Retreat

Conveniently located on the Bourbon Trail, our place will complete your experience! Next door is Shelbyville, the Saddlebred capital of the world, Lexington, the Thoroughbred capital and don't forget Louisville and Kentucky Derby. With a simplistic natural setting of a working horse farm there's nothing too fancy but comfortable and quaint. Our place is good for couples, solo adventurers, families (with kids), And groups!

Urban Loft Sleeps 16 and close to Buffalo Trace

"The biggest and best rental option in downtown Shelbyville, Urban Loft is the best place to stay in town. It’s an absolutely breathtaking space with enough sleeping space for well over a dozen guests to comfortably cohabitate, but the space is so absolutely picture perfect and secluded that you might have trouble coaxing all your traveling companions to ever leave." - Bourbon Review Magazine

Hot tub* sleeps 10* Fire pit*Come Stay!

Welcome to this Shelbyville Kentucky showstopper! Your group will love being centrally located to Louisville, Lexington, Lawrenceburg, Frankfort & so much more! 4 bedrooms(5 beds), 3 stunning full bathrooms, spacious living room, FULLY STOCKED kitchen with coffee, honey, creamers, and everything you'll need to prepare an incredible meal or gathering for your group! P.S.** more photos coming!!