Shelbyville Vacation Rentals

Name: Bourbon and Horse Racing
Price range: $356 total

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Vacation Rentals in Shelbyville

Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby

Shelbyville KY

When you stay at this vacation home in Shelbyville, you'll be 11 minutes by car from The Outlet Shoppes of the Bluegrass.

Kitchen

Washer

Secluded Retreat in Scenic Frankfort w/ Hot Tub: Whiskey Woods - Book Now!

Frankfort KY

$267 nightly

$302 total

Dec 9 - Dec 10

Total with taxes and fees

With a stay at this vacation home in Frankfort, you'll be next to a golf course, within a 15-minute drive of Buffalo Trace Distillery and Castle & Key Distillery.

Hot Tub

Kitchen

RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE

Pendleton KY

$212 nightly

$234 total

Dec 13 - Dec 14

Total with taxes and fees

Located in Pendleton, this vacation home is in a rural location, within a 15-minute drive of Morgan Conservation Park and LaGrange Main Street Visitor Center.

Kitchen

Washer

Spectacular waterfront house!

Prospect KY

Located in Prospect, this vacation home is on the waterfront, within a 15-minute drive of Ohio River Valley and Paddock Shops.

Hot Tub

Kitchen

Large Private Home close to Bourbon Trail!/POOL/Free Firewood/Parks/Close to I65

Shepherdsville KY

Located in Shepherdsville, this vacation home is in a rural location, within a 10-minute drive of McNeely Lake Park and Fairmount Falls Park.

Pool

Kitchen

"Centrally Located to Many Distilleries" House on the Kentucky Bourbon Trail

Frankfort KY

With a stay at this vacation home in Frankfort, you'll be on a river, within a 10-minute drive of Buffalo Trace Distillery and Greenhill Cemetery.

Kitchen

Washer

Centrally located retreat in Louisville! New hottub! Driveway and garage parking

Louisville KY

With a stay at this vacation home in Louisville (Avondale Melbourne Heights), you'll be within a 15-minute drive of Louisville Mega Cavern and Kentucky Kingdom.

Hot Tub

Kitchen

Open 4BR/2BA • Sleeps 8 • Huge Kitchen, Covered Deck & Easy Highway Access

Louisville KY

With a stay at this vacation home in Louisville (Hikes Point), you'll be within a 15-minute drive of Louisville Mega Cavern and Kentucky Exposition Center.

Kitchen

Washer

NEW Bourbon Trail Luxury Loft in Downtown Frankfort / 5 BR + 5 Bath / Sleeps 10

Frankfort KY

With a stay at this vacation home in Frankfort, you'll be within a 5-minute drive of Buffalo Trace Distillery and The Grand Theatre.

Kitchen

Washer

Luxury 5BR Estate: Bourbon Bar, Spa, Pool, 100"TV Cinema, 12 mins to Bardstown

Bloomfield KY

Located in Bloomfield, this vacation home is a 3-minute drive from Springhill Winery and 9 minutes from Chuckleberry Farm & Winery.

Pool

Hot Tub

Near Highways and a 20 Min Drive to Louisville's Main Attractions

Louisville KY

$339 nightly

$393 total

Jan 3 - Jan 4, 2026

Total with taxes and fees

With a stay at this vacation home in Louisville, you'll be a 1-minute walk from Beckley Creek Park and 12 minutes by foot from Barklands.

Kitchen

Washer

Bourbon and Horse Racing

Frankfort KY

$314 nightly

$356 total

Dec 9 - Dec 10

Total with taxes and fees

With a stay at this vacation home in Frankfort, you'll be within a 15-minute drive of Buffalo Trace Distillery and Josephine Sculpture Park.

Kitchen

Washer

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.