Shelbyville vacation rentals

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Best Shelbyville vacation rentals

Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi - Shelbyville - Building
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi
Shelbyville, KY
9.7Wonderful(19)
Apartment
$157+
Check availability
Shelbyville Farmhouse with Hot Tub, Fire Pit and Grill - Shelbyville - Living room
Shelbyville Farmhouse with Hot Tub, Fire Pit and Grill
Shelbyville, KY
9.1Wonderful(7)
House
Free Wi-Fi
Pet friendly
$473+
Check availability
Peaceful, lakefront house on Guist Creek Lake/ Shelbyville-Bourbon Trail - Shelbyville - Kitchen
Peaceful, lakefront house on Guist Creek Lake/ Shelbyville-Bourbon Trail
Shelbyville, KY
9.9Wonderful(42)
House
$452+
Check availability
Unique Downtown Studio with an Industrial Vibe - Shelbyville - Lounge
Unique Downtown Studio with an Industrial Vibe
Shelbyville, KY
9.7Wonderful(27)
Apartment
$179+
Check availability
Ky Bourbon Trail Home, King Bed, Firepit, Near Louisville - Shelbyville - Bedroom
Ky Bourbon Trail Home, King Bed, Firepit, Near Louisville
Shelbyville, KY
10Wonderful(7)
Cottage
Free Wi-Fi
$288+
Check availability
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby - Shelbyville - Living room
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby
Shelbyville, KY
9.2Wonderful(28)
House
Free Wi-Fi
$268+
Check availability
Historic home freshly renovated on the Bourbon Trail - Shelbyville - Living room
Historic home freshly renovated on the Bourbon Trail
Shelbyville, KY
10Wonderful(7)
House
Free Wi-Fi
$301+
Check availability
The Gatsby and adjoining ceilings - Shelbyville - Living room
The Gatsby and adjoining ceilings
Shelbyville, KY
10Wonderful(13)
House
$4,905+
Check availability
LeCoop Ultra Luxury 2 bed Loft on Bourbon Trail.Close to BuffaloTrace and others - Shelbyville - Living room
LeCoop Ultra Luxury 2 bed Loft on Bourbon Trail.Close to BuffaloTrace and others
Shelbyville, KY
9.7Wonderful(35)
Apartment
$299+
Check availability
Heritage House 1900’s home part/close to the Bourbon Trail - Shelbyville - Living room
Heritage House 1900’s home part/close to the Bourbon Trail
Shelbyville, KY
10Wonderful(14)
House
Free Wi-Fi
$394+
Check availability
Beautiful restored Victorian farmhouse - Shelbyville - Kitchen
Beautiful restored Victorian farmhouse
Shelbyville, KY
9.1Wonderful(12)
Cottage
$440+
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2025 KY Derby 30 min Away ~ Bourbon Trail ~ Hot Tub - Shelbyville - Living room
2025 KY Derby 30 min Away ~ Bourbon Trail ~ Hot Tub
Shelbyville, KY
9.8Wonderful(26)
Cottage
Free Wi-Fi
$359+
Check availability
Cozy cottage on beautiful Chickapoo Farm with amazing views. - Shelbyville - Patio
Cozy cottage on beautiful Chickapoo Farm with amazing views.
Shelbyville, KY
9.5Wonderful(4)
Agritourism
$241+
Check availability
Shelbyville Farm studio close to hiking, horses, Kentucky derby and distillery’s - Shelbyville - Kitchen
Shelbyville Farm studio close to hiking, horses, Kentucky derby and distillery’s
Shelbyville, KY
10Wonderful(4)
Apartment
$183+
Check availability
Arcade | Fishing Pond | Cabin on Farm | Slps 12+ - Shelbyville - Living room
Arcade | Fishing Pond | Cabin on Farm | Slps 12+
Shelbyville, KY
9.0Wonderful(4)
Cabin
$739+
Check availability
Shelbyville Home - On to the Bourbon Trail! - Shelbyville - Living room
Shelbyville Home - On to the Bourbon Trail!
Shelbyville, KY
7.3Good(12)
House
Free Wi-Fi
$436+
Check availability
Useful Info

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

July
September
$564
$225
Cheapest month to stay with an average 31% drop in price.
Most expensive month to stay with an average 122% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Shelbyville vacation rental deals

  • Vacation rentals in Shelbyville are around 72% more expensive than hotels on average. Search here to compare prices for all accommodation types in Shelbyville.
  • The best vacation rental properties in Shelbyville are Peaceful, lakefront house on Guist Creek Lake/ Shelbyville-Bourbon Trail (9.9, 42 reviews), 2025 KY Derby 30 min Away ~ Bourbon Trail ~ Hot Tub (9.8, 26), and Urban Loft 5,000 Sqft. Sleeps 17 Next To Frankfort Distilleries,perfect Location (9.8, 37), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Shelbyville, you should consider visiting during the low season. The cheapest vacation homes in Shelbyville can be found in July and October.
  • The cheapest night for renting a vacation home in Shelbyville is Friday. In contrast, the most expensive is Wednesday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Shelbyville for 27 days.

FAQs when booking a vacation home in Shelbyville

  • What types of vacation rentals are available in Shelbyville?

    There are loads of different property types that you can make your vacation home in Shelbyville. You’ll find agritourism, apartments, cabins, condos, cottages and houses.

  • Are there any pet-friendly vacation rentals in Shelbyville?

    There are a number of dog and pet-friendly Shelbyville vacation rentals, with around 4% allowing you to bring your pet along with you.

  • How can I find vacation rentals near me in Shelbyville?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Shelbyville?

Our map will help you find the perfect place to stay in Shelbyville by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Shelbyville