Upscale Kentucky Bourbon Trail & Close to Louisville

Welcome to The Oak, an upscale first floor 2-bedroom, 2-bath retreat in the heart of Kentucky's Bourbon Trail. Located in historic downtown Shelbyville, this 1909 house has been painstakingly restored to highlight its charm. Enjoy tasteful décor (including local artwork by the 148th Kentucky Derby artist), plush furnishings, and a fully-equipped kitchen. Relax on the patio or enjoy boardgames after a day at the famous bourbon distilleries and horse farms. Walk to dinner and shops. Retreat to elegant bedrooms with premium linens. The Oak offers the perfect base for bourbon and horse enthusiasts. Book now for a memorable experience of luxury and comfort.

The Oak is located at 1029 Main Street. Experience the smalltown charm of historic Shelbyville Kentucky, where you can walk to local boutique shops and restaurants. Shelbyville is the Saddlebred Capital of the World and boasts a central location between Louisville, Lexington and Bardstown in the heart of the Kentucky Bourbon Trail. Connect with locals, embrace the culture, and create memorable moments at The Oak in Shelbyville, KY.


The Property

We offer 2 queen bedrooms and 2 full bathrooms with tiled showers, 1 of which is ensuite.

We offer a living space complete with a living room, a smart TV and a fully stocked kitchen.

We also offer a covered patio and grill for your evening BBQ. (It is shared with our connected property the Copper)

Kitchen-The fully stocked kitchen is ready for guests to eat, drink and be merry. Each has an attached dining space for 4

Coffee- A Keurig Coffee machine is provided along with enough pods, sweeteners, and creamer to get you started.

Enjoy cards and boards games with friends and family for added enjoyment

Two private off street parking spaces are available at the rear of the property.

Guest access
Guests will have full access to the property other than the garage area. Please note that the Oak is a 1st Story Unit.

Other Items of interest
Signature cocktail welcome kit included featuring local bitters and mixer (BYOB- Bring your own Bourbon)
Bathroom toiletries provided (shampoo, conditioner, body wash, lotion, bar soap)
Contactless check in and check out through our smart lock system


If your visit includes the bourbon trail, please make your tour reservations well in advance as spaces fill up fast.

Within a 50 mile radius of The Oak you'll find dozens of the most famous bourbon distilleries offering unique flavors and experiences (and you'll enjoy Kentucky's scenic countryside and horse farms along the way).

Bulleit Distilling Co. (4 mi)
Jeptha Creed Distillery (4.8 mi)
Whiskey Thief Distilling Co. (14 mi)
Heaven's Door Distillery (coming Sept. 2023) (14 mi)
Kentucky Artisan Distillery (20 mi)
Buffalo Trace Distillery (23 mi.)
Wild Turkey Distillery (26 mi)
Castle & Key Distillery (28 mi)
Four Roses Distillery (29 mi)
Woodford Reserve Distillery (30 mi)
Rabbit Hole Distillery (30 mi)
Angel's Envy Distillery (31 mi)
Old Forester Distilling Co. (32 mi)
Michter's Fort Nelson Distillery (32 mi)
Evan Williams Experience (32 mi)
Peerless Distillery (32 mi)
Copper & Kings (34 mi)
Stitzel-Weller Distillery (37 mi)
Bardstown Bourbon Co. (40 mi)
Lux Row Distillers (41 mi)
Heaven Hill Distillery (42 mi)
Willett Distillery (43 mi)
RD1 Spirits (44 mi)
Preservation Distillery (44 mi)
Jim Beam Distilling Co. (46 mi)


Other Kentucky experiences you won't want to miss:
Shelby Co. Fairgrounds and Horse Show (0.8 mi)
Valhalla Golf Course (14 mi)
Kentucky's historic Capitol (20 mi)
Churchill Downs & Kentucky Derby Museum (31 mi)
Belle of Louisville Riverboat (31 mi)
Louisville Slugger Museum (32 mi)
Keeneland Racetrack (40 mi)
Kentucky Horse Park (46 mi)
No candles are allowed to be burned in the home.
No one other than guests within the reservation are permitted to stay at the home.
To Ensure a smooth stay, guests will be required to review and sign our rental agreement upon booking confirmation.