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Search results; Over 1,000 homes in Shelbyville

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Guest favourite
Farm stay in Shelbyville
Horse &Hound Bourbon Trail Retreat@Chickapoo Farm
3 bedrooms, 4 beds, 2 private bathrooms
1–6 Sept
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5.0 out of 5 average rating, 16 reviews
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Guest favourite
Home in Simpsonville
Luxury Country Retreat w 7 Bedroom | Bourbon Trail
7 bedrooms, 7 beds, 3.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 8 reviews
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Guest favourite
Loft in Shelbyville
Sleeps 16/near everything-Transportation available
5 bedrooms, 7 beds, 3.5 bathrooms
1–6 Sept
4.99 out of 5 average rating, 142 reviews
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Top guest favourite
Home in Shelbyville
Kentucky Estate: Speakeasy, Theater & Sleeps 20
8 bedrooms, 11 beds, 4.5 bathrooms
15–20 Sept
4.99 out of 5 average rating, 67 reviews
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Top guest favourite
Home in Shelbyville
Luxury Manor 8BR 16 Beds HeatedPool~Sauna~ HotTubs
7 bedrooms, 16 beds, 4.5 bathrooms
17–22 Oct
5.0 out of 5 average rating, 19 reviews
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Guest favourite
Loft in Shelbyville
Close to Buffalo Trace/Transpo available-Must See
5 bedrooms, 5 beds, 3 bathrooms
1–6 Sept
4.98 out of 5 average rating, 123 reviews
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Farm stay in Simpsonville
Restored 1919 Farmhouse on 100 Private Acres
4 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
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Guest favourite
Flat in Shelbyville
Downtown Main St 1-Bedroom Suite w/ Hi-Speed Wifi
1 bedroom, 1 queen bed, 1 bathroom
1–6 Sept
4.96 out of 5 average rating, 79 reviews
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Cabin in Shelbyville
Cozy Hillside Cabin, Slps 20+, Speakeasy + Hot Tub
4 bedrooms, 11 beds, 3.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 37 reviews
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Top guest favourite
Home in Waddy
Private A-frame Cabin | Hot tub, Firepit & Views
2 bedrooms, 4 beds, 2 bathrooms
6–11 Sept
4.98 out of 5 average rating, 45 reviews
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Top guest favourite
Farm stay in Shelbyville
Lux Horse Farm * Pklball * Swim Spa * Sauna * Golf * Speakeasy
7 bedrooms, 8 beds, 4 bathrooms
15–20 Nov
5.0 out of 5 average rating, 42 reviews
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Top guest favourite
Loft in Shelbyville
The Stick at Pondview
3 bedrooms, 4 beds, 1 bathroom
18–23 Oct
5.0 out of 5 average rating, 18 reviews
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Top guest favourite
Home in Shelbyville
Peaceful Bourbon trail home POOL hot tub 3 kings
4 bedrooms, 5 beds, 2.5 bathrooms
14–19 Sept
4.93 out of 5 average rating, 72 reviews
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Room in Shelbyville
Near Weissinger Hills Golf Course + Free Breakfast
2 queen beds, 1 bathroom
1–6 Sept
4.67 out of 5 average rating, 3 reviews
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Guest favourite
Home in Shelbyville
Hitching Post on the Bourbon Trl
5 bedrooms, 6 beds, 3 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 12 reviews
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Top guest favourite
Cabin in Waddy
Landmark Luxury Lodge in the heart of the Blugrass
5 bedrooms, 10 beds, 4 bathrooms
6–11 Sept
4.99 out of 5 average rating, 92 reviews
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Guest favourite
Farm stay in Shelbyville
A truly Kentucky experience on the Bourbon Trail
4 bedrooms, 7 beds, 4.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Home in Waddy
The Ridge: 6BR • 100" TV • Hot Tub • Speakeasy
6 bedrooms, 10 beds, 3 bathrooms
20–25 Sept
4.96 out of 5 average rating, 28 reviews
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Top guest favourite
Home in Simpsonville
Sleeps 26, Hot Tub & Sauna - Near Bourbon Trail
6 bedrooms, 14 beds, 4 bathrooms
5–11 Oct
5.0 out of 5 average rating, 15 reviews