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Search results; Over 1,000 homes in Shelbyville

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Guest favourite
Flat in Shelbyville
End of Summer Vacation Getaway
6 bedrooms, 6 beds, 6 private bathrooms
26–31 Oct
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4.94 out of 5 average rating, 17 reviews
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Home in Simpsonville
Luxury Country Retreat w 7 Bedroom | Bourbon Trail
7 bedrooms, 7 beds
1–6 Sept
5.0 out of 5 average rating, 8 reviews
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Loft in Shelbyville
Sleeps 16/near everything-Transportation available
5 bedrooms, 7 beds
1–6 Sept
4.99 out of 5 average rating, 142 reviews
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Home in Shelbyville
Kentucky Estate: Speakeasy, Theater & Sleeps 20
8 bedrooms, 11 beds
15–20 Sept
4.99 out of 5 average rating, 67 reviews
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Cabin in Shelbyville
The Rec Farm-Log Cabin, Private Lake & Arcade
3 bedrooms, 7 beds
13–18 Sept
5.0 out of 5 average rating, 21 reviews
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Flat in Shelbyville
Unique Downtown Studio with an Industrial Vibe
1 bedroom, 1 queen bed
12–17 Sept
4.97 out of 5 average rating, 145 reviews
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Top guest favourite
Home in Shelbyville
Luxury Manor 8BR 16 Beds HeatedPool~Sauna~ HotTubs
7 bedrooms, 16 beds
17–22 Oct
5.0 out of 5 average rating, 21 reviews
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Home in Shelbyville
Long Ridge Farm
3 bedrooms, 4 beds
7–12 Sept
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Loft in Shelbyville
The Stick at Pondview
3 bedrooms, 4 beds
18–23 Oct
5.0 out of 5 average rating, 18 reviews
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Home in Waddy
Cabin Escape | Hot Tub, Game Room & Fire Pit
2 bedrooms, 4 beds
6–11 Sept
4.98 out of 5 average rating, 45 reviews
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Guest favourite
Farm stay in Shelbyville
Horse &Hound Bourbon Trail Retreat@Chickapoo Farm
3 bedrooms, 4 beds
1–6 Sept
5.0 out of 5 average rating, 16 reviews
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Farm stay in Simpsonville
Restored 1919 Farmhouse on 100 Private Acres
4 bedrooms, 3 beds
1–6 Sept
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Top guest favourite
Home in Shelbyville
Peaceful Bourbon trail home POOL hot tub 3 kings
4 bedrooms, 5 beds
14–19 Sept
4.93 out of 5 average rating, 73 reviews
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Farm stay in Shelbyville
A truly Kentucky experience on the Bourbon Trail
4 bedrooms, 7 beds
7–12 Sept
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Apartment in Shelbyville
Modern cozy condo, family, friends & bourbon trail
2 bedrooms, 2 beds
7–12 Sept
4.94 out of 5 average rating, 159 reviews
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Home in Shelbyville
The Hutch on Hardesty
1 bedroom, 2 beds
5–10 Oct
4.96 out of 5 average rating, 27 reviews
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Home in Shelbyville
Hitching Post on the Bourbon Trl
5 bedrooms, 6 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 12 reviews
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Cabin in Waddy
Landmark Luxury Lodge in the heart of the Blugrass
5 bedrooms, 10 beds
6–11 Sept
4.99 out of 5 average rating, 92 reviews
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Home in Shelbyville
Bourbon Trail*Hot Tub*Sauna*Mini Golf*Wi-Fi*EVSE
3 bedrooms, 4 beds
30 Oct – 4 Nov
5.0 out of 5 average rating, 89 reviews