Home Vacation Home Rentals By Owner In Shelbyville, KY

Showing 20 Of 33 Vacation Rentals
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$755.62

/ Nightly
Private Vacation Home

Your Kentucky Bourbon Trail stay hosted by Sixteen Chairs with panoramic horse country views, barrel sauna, cold plunge, hot tub, gym, game room, theatre room, and dedicated outdoor space

Shelbyville, Kentucky, United States

Bed 4

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(8)

$432.98

/ Nightly
Private Vacation Home

Hot Tub | Firepit | Putting Green | 5 Bedrooms

Shelbyville, Kentucky, United States

Bed 5

Bed

Bath 3

Bath

Sleep 12

Sleeps
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Exceptional(19)

$447.43

/ Nightly
Private Vacation Home

Beautiful, Peaceful Lakefront home in ❤️ of Bourbon Country in Shelbyville, KY

Shelbyville, Kentucky, United States

Bed 4

Bed

Bath 2

Bath

Sleep 7

Sleeps
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Exceptional(43)

$474.78

/ Nightly
Private Vacation Home

Historic 1909 Gem on the Bourbon Trail w/4 King Beds

Shelbyville, Kentucky, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
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Exceptional(16)

$477.48

/ Nightly
Private Vacation Home

6 Mi to Bourbon Trail: Group Estate on 20 Acres

Shelbyville, Kentucky, United States

Bed 5

Bed

Bath 4

Bath

Sleep 10

Sleeps
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Exceptional(1)

$525.29

/ Nightly
Private Vacation Home

Lakefront - Bourbon Trl - Hot Tub

Shelbyville, Kentucky, United States

Bed 4

Bed

Bath 2

Bath

Sleep 10

Sleeps
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$554.38

/ Nightly
Private Vacation Home

the bourbon barrel escape HotTub Game Room pets ok

Shelbyville, Kentucky, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(23)

$637.61

/ Nightly
Private Vacation Home

Bourbon Trail! Game Room Hot Tub Speakeasy FirePit

Shelbyville, Kentucky, United States

Bed 3

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(2)

$658.15

/ Nightly
Private Vacation Home

Family & Pet Friendly, Fire Pit, Two Hot Tubs, Country Views, Theatre Room

Shelbyville, Kentucky, United States

Bed 5

Bed

Bath 3

Bath

Sleep 16

Sleeps
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$430.23

/ Nightly
Private Vacation Home

Haven of the Bluegrass | Bourbon Trail Getaway!

Shelbyville, Kentucky, United States

Bed 3

Bed

Bath 2

Bath

Sleep 10

Sleeps
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$784.99

/ Nightly
Private Vacation Home

Two Hot Tubs, Pet Friendly, BBQ,,, Theatre Room

Shelbyville, Kentucky, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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Exceptional(6)

$883.72

/ Nightly
Private Vacation Home

Historic Home Farm Stay in the Heart of Bourbon Country

Shelbyville, Kentucky, United States

Bed 4

Bed

Bath 4

Bath

Sleep 12

Sleeps
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Exceptional(4)

$986.22

/ Nightly
Private Vacation Home

Shelby Stop on Bourbon Trail- HOT TUB and Pool. Pool is now Open

Shelbyville, Kentucky, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(4)

$1026.24

/ Nightly
Private Vacation Home

Speakeasy w/heated pool, hot tub, pond, game room

Shelbyville, Kentucky, United States

Bed 8

Bed

Bath 7

Bath

Sleep 16

Sleeps
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Exceptional(5)

$1149.15

/ Nightly
Private Vacation Home

Speakeasy, Hot Tub, Theater, Pickle Ball, Sleeps 20

Shelbyville, Kentucky, United States

Bed 8

Bed

Bath 4

Bath

Sleep 20

Sleeps
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Exceptional(6)

$1263.47

/ Nightly
Private Vacation Home

Heated Pool~2 hottubs~ Barrel Sauna~Theatre~PS5 Lounge~ 16 BEDS~ Eminence Downs

Shelbyville, Kentucky, United States

Bed 7

Bed

Bath 4

Bath

Sleep 25

Sleeps
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Exceptional(7)

$1661.71

/ Nightly
Private Vacation Home

Flint Ridge Reserve - Sleeps 29 Heated PoolHotTub - Golf Sim - Arcade - Games

Shelbyville, Kentucky, United States

Bed 10

Bed

Bath 5

Bath

Sleep 29

Sleeps
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Exceptional(4)

$171.62

/ Nightly
Private Vacation Home

Lakefront Retreat: Fishing, Family, Fire Pit & Bourbon Trail

Shelbyville, Kentucky, United States

Bed 1

Bed

Bath 1

Bath

Sleep 3

Sleeps
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Exceptional(10)

$420.16

/ Nightly
Private Vacation Home

Bourbon Trail, Hot Tub, Pool, Quiet/Peaceful Location, 3 King Beds

Shelbyville, Kentucky, United States

Bed 4

Bed

Bath 2

Bath

Sleep 9

Sleeps
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Exceptional(9)

$412.23

/ Nightly
Private Vacation Home

Bourbon Trail Retreat . Sleeps 10 + Hot Tub. In the Heart of the Bourbon Trail

Shelbyville, Kentucky, United States

Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Home Most popular vacation rentals in Shelbyville

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Exceptional(9)

$296.75

/ Nightly
Private vacation home

Historic Gem on the Bourbon Trail at The Copper

Shelbyville, Kentucky, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps
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Exceptional(9)

$407.65

/ Nightly
Private vacation home

Hitching Post on the Bourbon Trl

Shelbyville, Kentucky, United States

Bed 5

Bed

Bath 3

Bath

Sleep 12

Sleeps
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Exceptional(9)

$405.69

/ Nightly
Private vacation home

Heritage House 1900’s home part/close to the Bourbon Trail

Shelbyville, Kentucky, United States

Bed 3

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(9)

$402.54

/ Nightly
Private vacation home

The Horse & Hound Bourbon Trail Retreat at Chickapoo Farm

Shelbyville, Kentucky, United States

Bed 3

Bed

Bath 2

Bath

Sleep 7

Sleeps
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Exceptional(9)

$391.22

/ Nightly
Agritourism

The Country Pleasure Farm – Where Rustic Charm Meets Relaxation

Shelbyville, Kentucky, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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Exceptional(9)

$350.88

/ Nightly
Private vacation home

Quiet Downtown Maple Cottage Gem

Shelbyville, Kentucky, United States

Bed 0

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(9)

$342.25

/ Nightly
Private vacation home

Brown Ave Bourbon Trail & Beds- Shelbyville, KY

Shelbyville, Kentucky, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(9)

$332.79

/ Nightly
Agritourism

Farm Stay! Horses welcome! On the bourbon trail between Lexington and Louisville

Shelbyville, Kentucky, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(9)

$184.32

/ Nightly
Apartment

Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

Shelbyville, Kentucky, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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Exceptional(9)

$205.91

/ Nightly
Apartment

Shelbyville Farm studio close to hiking, horses, Kentucky derby and distillery’s

Shelbyville, Kentucky, United States

Bed 1

Bed

Bath 1

Bath

Sleep 3

Sleeps

Most Popular Cities in Kentucky