Vacation Rentals By Owner In Shelbyville, KY

Showing 40 Of 61 Vacation Rentals

Exceptional(19)

$447.43

/ Nightly

Private Vacation Home

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

Shelbyville, Kentucky, United States

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Bath

Sleeps

Exceptional(7)

$391.22

/ Nightly

Agritourism

The Country Pleasure Farm – Where Rustic Charm Meets Relaxation

Shelbyville, Kentucky, United States

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Bath

Sleeps

$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

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Bath

Sleeps

Exceptional(7)

$388.87

/ Nightly

Private Vacation Home

Bourbon Trail*Hot Tub*Sauna*Mini Golf*WiFi*EVSE

Shelbyville, Kentucky, United States

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Bath

Sleeps

Exceptional(7)

$1661.71

/ Nightly

Private Vacation Home

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

Shelbyville, Kentucky, United States

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Sleeps

Exceptional(2)

$658.15

/ Nightly

Private Vacation Home

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

Shelbyville, Kentucky, United States

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Sleeps

Exceptional(13)

$395.66

/ Nightly

Agritourism

Peace and Quiet Close to Louisville - 80+ Acres

Shelbyville, Kentucky, United States

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Sleeps

Exceptional(21)

$405.69

/ Nightly

Private Vacation Home

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

Shelbyville, Kentucky, United States

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Bath

Sleeps

Exceptional(4)

$1026.24

/ Nightly

Private Vacation Home

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

Shelbyville, Kentucky, United States

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Sleeps

Exceptional(42)

$519.59

/ Nightly

Agritourism

Bourbon Trail Farmhouse w/ Hot Tub & Fenced Yard

Shelbyville, Kentucky, United States

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Bath

Sleeps

Exceptional(6)

$305.52

/ Nightly

Private Vacation Home

Shelbyville, KY - Bourbon Trail, Horse Country and more. A modern, spacious gem.

Shelbyville, Kentucky, United States

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Sleeps

Exceptional(10)

$526.45

/ Nightly

Cabin

The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade, Pickle Ball, Sleeps 12+

Shelbyville, Kentucky, United States

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Bath

Sleeps

Exceptional(6)

$282.15

/ Nightly

Condo

Charming 3-bedroom Loft on the Bourbon Trail.

Shelbyville, Kentucky, United States

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Bath

Sleeps

Exceptional(1)

$296.75

/ Nightly

Private Vacation Home

Historic Gem on the Bourbon Trail at The Copper

Shelbyville, Kentucky, United States

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Bath

Sleeps

Exceptional(4)

$171.62

/ Nightly

Private Vacation Home

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

Shelbyville, Kentucky, United States

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Bath

Sleeps

Exceptional(8)

$432.98

/ Nightly

Private Vacation Home

Hot Tub | Firepit | Putting Green | 5 Bedrooms

Shelbyville, Kentucky, United States

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Bath

Sleeps

Exceptional(8)

$272.08

/ Nightly

Cottage

KY Bourbon Trail Home, King Bed, FirePit, Near Louisville

Shelbyville, Kentucky, United States

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Sleeps

Exceptional(2)

$239.15

/ Nightly

Private Vacation Home

Spacious 4-bedroom house Shelbyville 1 mile from I-64

Shelbyville, Kentucky, United States

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Bath

Sleeps

Exceptional(1)

$424.61

/ Nightly

Lodge

Spacious charming exclusive rental in Shelbyville, KY

Shelbyville, Kentucky, United States

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Bath

Sleeps

Exceptional(43)

$474.78

/ Nightly

Private Vacation Home

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

Shelbyville, Kentucky, United States

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Rent a place that suits your needs

Private vacation home

View 33 Private vacation home

Most popular vacation rentals in Shelbyville

Exceptional(43)

$296.75

/ Nightly

Private vacation home

Historic Gem on the Bourbon Trail at The Copper

Shelbyville, Kentucky, United States

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Bath

Sleeps

Exceptional(43)

$407.65

/ Nightly

Private vacation home

Hitching Post on the Bourbon Trl

Shelbyville, Kentucky, United States

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Bath

Sleeps

Exceptional(43)

$405.69

/ Nightly

Private vacation home

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

Shelbyville, Kentucky, United States

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Bath

Sleeps

Exceptional(43)

$402.54

/ Nightly

Private vacation home

The Horse & Hound Bourbon Trail Retreat at Chickapoo Farm

Shelbyville, Kentucky, United States

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Bath

Sleeps

Exceptional(43)

$391.22

/ Nightly

Agritourism

The Country Pleasure Farm – Where Rustic Charm Meets Relaxation

Shelbyville, Kentucky, United States

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Bath

Sleeps

Exceptional(43)

$350.88

/ Nightly

Private vacation home

Quiet Downtown Maple Cottage Gem

Shelbyville, Kentucky, United States

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Bath

Sleeps

Exceptional(43)

$342.25

/ Nightly

Private vacation home

Brown Ave Bourbon Trail & Beds- Shelbyville, KY

Shelbyville, Kentucky, United States

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Bath

Sleeps

Exceptional(43)

$332.79

/ Nightly

Agritourism

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

Shelbyville, Kentucky, United States

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Sleeps

Exceptional(43)

$184.32

/ Nightly

Apartment

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

Shelbyville, Kentucky, United States

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Bath

Sleeps

Exceptional(43)

$205.91

/ Nightly

Apartment

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

Shelbyville, Kentucky, United States

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Bath

Sleeps

Vacation Rentals By Owner In Shelbyville, KY

$447.43

$391.22

$755.62

$388.87

$1661.71

$658.15

$395.66

$405.69

$1026.24

$519.59

$305.52

$526.45

$282.15

$296.75

$171.62

$432.98

$272.08

$239.15

$424.61

$474.78

Rent a place that suits your needs

Most popular vacation rentals in Shelbyville

$296.75

$407.65

$405.69

$402.54

$391.22

$350.88

$342.25

$332.79

$184.32

$205.91

Most Popular Cities in Kentucky