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Homes on the Bourbon Trail

Simpsonville and Shelbyville, ten minutes from Bulleit and half an hour from Whiskey Row.

LexingtonBourbon TrailWilliamstownAsheville

2 homes on the Bourbon Trail

2 family-owned homes on the Bourbon Trail, sleeping 12 to 12, from $178 a night. 10 min to Bulleit. Every home is owned and managed by the Hillenmeyer family, and booking here adds no listing-site service fee.

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119 Adair Ave

Shelbyville, Kentucky · 10 min to Bulleit

Picture this: the fire pit crackles while bourbon stories spill into the Kentucky night, steam rises off the hot tub under string lights, and someone's lining up a putt on your own backyard green. Ten of your favorite people, one quiet Shelbyville street, minutes from…

12
Guests
5
Bedrooms
5
Beds
3.0
Baths
from $178 / night · Book a stay
Pull a chair around the fire the second the sun drops — string lights flicker on, the hot tub's already glowing behind you, and this is where the whole trip starts to slow down.You'll want to line up a putt while the fire pit glows just behind you — one more reason to stay outside before heading in for the night.Cook shoulder-to-shoulder at the island while someone perches on a stool planning tomorrow's distillery stops — you won't be doing this meal alone.Kick your boots off and claim the couch — the fireplace crackling, the big TV on for the game, this is the room where the group actually slows down together.Pull up after a day of tastings and know you're home — porch lights on, hydrangeas framing the walk, a quiet street that doesn't feel like a rental block.

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9790 Shelbyville Rd

Simpsonville, Kentucky · 10 min to Bulleit

Picture it: the Kentucky hills roll out in every direction, the pool shimmers in the afternoon sun, and twelve of your people are already arguing over who gets the golf simulator first. That is a Sixgen Rentals estate — 10 private acres, zero neighbors, French-country…

12
Guests
6
Bedrooms
5
Beds
4.5
Baths
from $300 / night · Book a stay
Pull up at dusk and you'll know you made the right call — this stone French-country manor lit against a purple Kentucky sky is the arrival moment your group will talk about all weekend.Look down at the pool deck from above and you'll see why this property books early — rectangular pool, hot tub at the end, pergola lounge in the corner. Your private resort.Your whole afternoon, right here — heated pool, attached hot tub, pergola with outdoor seating, and 10 private acres with not a neighbor in sight. Pick your spot and settle in.Step into the golf simulator and stay as long as you want — projection screen, LED ambiance, putting green just outside, and zero tee times. No one else is waiting.The kind of kitchen where you actually cook — marble island, stainless appliances, and enough bar stool seating that the chef stays in the conversation. Meals for twelve start here.

Where they are

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Keep reading

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Ten percent off your first stay

Join the list for first look at open Keeneland weekends, Ark holiday weeks and leaf season.

26
Homes
4.9
1,240 reviews
T+L
Top 10 · Lexington
6
Generations