ONLY STEPS AWAY
SLEEP IN SPLENDOR
AN INVITATION
EXTENDED
AFTERWORD
Evenings at The Gatsby don’t end with the final toast—they linger, stretch, and spill over into the kind of night that deserves a morning just as refined. For guests attending your event, When in Roam offers a curated collection of luxury stays designed to extend the enchantment.
These handpicked properties are perfect for wedding parties and close family, out-of-town guests, and couples eager to savor the weekend in full Gatsby fashion.
SHELBYVILLE STAYS
URBAN LOFT
16+ GUESTS • 6 BEDROOMS • 8 BEDS • 3.5 BATHS
A rare gem along the Bourbon Trail, this high-end residence blends refined luxury with Kentucky soul, making it a destination of its own. Perfectly positioned on East Main, near beloved local eateries, craft cocktail bars, and cultural gems, this immersive suite is just moments from the experiences that make your stay unforgettable.
BOTTLED-IN-BOND LOFT
10 GUESTS • 5 BEDROOMS • 5 BEDS • 3 BATHS
As featured on HGTV and adjoined to The Gatsby, this architectural gem blends the charm of its 1800s origins with cinematic style—imagine a rendezvous between a James Bond film and a speakeasy fantasy. Enter through a vintage revolving door or glide up via elevator and step into a space pulsing with personality, history, and undeniable swagger.
LECOOP LOFT
5 GUESTS • 2 BEDROOMS • 2 BEDS • 2 BATHS
Tucked in the storied charm of downtown Shelbyville, LeCoop is a two-bedroom loft. Walk to cafés, cocktails, and conversation; only a scenic drive from Kentucky’s most iconic distilleries and racetracks—this retreat pairs intimacy with access. A stay here is convenient, intentional, and unmistakably well-placed: steps from the Gatsby’s front door.