ONLY STEPS AWAY

SLEEP IN
SPLENDOR

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.

EXTENDED

AN INVITATION

SHELBYVILLE STAYS

Living room with a large gray sectional sofa, a rustic coffee table, white bookshelves, and various decor items under a high open ceiling with exposed wooden beams.

Urban Loft

16+ GUESTS • 5 BEDROOMS • 7 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.

EXPLORE URBAN LOFT
A spacious, industrial-style living room with exposed brick walls, wooden ceiling beams, and large arched windows. It features a gray sectional sofa with numerous throw pillows, a small wooden coffee table on a plush rug, and black glass partitions with gold light fixtures hanging above.

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.

EXPLORE BOND LOFT
Living room with exposed wooden beams, brick and painted walls, white kitchen cabinets, bar seating, and modern lighting fixtures.

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.

EXPLORE LECOOP

FRANKFORT STAYS

Living room with large windows, exposed brick wall, blue sectional sofa, white armchairs, modern lighting fixture, and wall-mounted TV.

Senate Floor

10 GUESTS • 5 BEDROOMS • 5 BEDS • 5 BATHS

An incredible location, the Senate Floor is the entire second floor of the historic Mason & Hoge building on Main Street of downtown Frankfort at the mouth of the Kentucky Bourbon Trail. You're just a short walk to the favorited Buffalo Trace Distillery as well as several local restaurants and bars.

EXPLORE SENATE FLOOR
Indoor staircase with green walls, patterned carpet, and modern design accents.

Parliament Penthouse

16 GUESTS • 6 BEDROOMS • 10 BEDS • 5 BATHS

Just steps from the iconic Buffalo Trace Distillery, this mesmerizing space isn't just a place to stay—it's a rare destination in itself. You can expect an experience that goes beyond hospitality—this is memory-making at its finest. A short, scenic drive from Shelbyville, cap your night out with a night in at this luxurious stay.

EXPLORE PARLIAMENT
A living room with exposed brick walls, a large window with white curtains, and eclectic furniture including a white sofa, matching armchair, wooden coffee table, and a round dining table with chairs. There's a small side table with a lamp, hanging pendant lights, and a decorative chandelier.

Neutral Ground

2 GUESTS • 1 BEDROOM • 1 BED • 1 BATH

Tucked within walking distance of Kentucky’s charming capital, this thoughtfully curated suite invites the curious traveler to indulge in a stay that’s equal parts luxurious and intimate. Steps from bourbon bars, locally roasted coffee, vibrant restaurants, and boutique shops,

EXPLORE NEUTRAL GROUND