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Search results; Over 1,000 homes in Shelbyville

Guest favourite
Loft in Shelbyville
Close to Buffalo Trace/Transpo available-Must See
5 bedrooms, 5 beds, 3 private bathrooms
13–18 Sept
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4.98 out of 5 average rating, 124 reviews
Guest favourite
Home in Simpsonville
Luxury Country Retreat w 7 Bedroom | Bourbon Trail
7 bedrooms, 7 beds, 3.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 8 reviews
Home in Shelbyville
Long Ridge Farm
3 bedrooms, 4 beds, 2.5 bathrooms
8–13 Sept
Guest favourite
Loft in Shelbyville
Sleeps 16/near everything-Transportation available
5 bedrooms, 7 beds, 3.5 bathrooms
8–13 Sept
4.99 out of 5 average rating, 142 reviews
Top guest favourite
Home in Finchville
Country Retreat on Bourbon Trail - Fire Pit - King
2 bedrooms, 2 beds, 1 bathroom
29 Sept – 4 Oct
5.0 out of 5 average rating, 91 reviews
Top guest favourite
Cabin in Waddy
Landmark Luxury Lodge in the heart of the Blugrass
5 bedrooms, 10 beds, 4 bathrooms
8–13 Sept
4.99 out of 5 average rating, 92 reviews
Top guest favourite
Farm stay in Shelbyville
A truly Kentucky experience on the Bourbon Trail
4 bedrooms, 7 beds, 4.5 bathrooms
9–14 Sept
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Rooms in Simpsonville
Slice Of Bourbon Country 2 BR FreshBreakfast
2 bedrooms, 2 beds, 1.5 bathrooms
17–22 Oct
5.0 out of 5 average rating, 53 reviews
Top guest favourite
Flat in Shelbyville
Unique Downtown Studio with an Industrial Vibe
1 bedroom, 1 queen bed, 1 bathroom
12–17 Sept
4.97 out of 5 average rating, 146 reviews
Top guest favourite
Home in Waddy
Cabin Escape | Hot Tub, Game Room & Fire Pit
2 bedrooms, 4 beds, 2 bathrooms
3–8 Oct
4.98 out of 5 average rating, 45 reviews
Guest favourite
Farm stay in Shelbyville
Horse &Hound Bourbon Trail Retreat@Chickapoo Farm
3 bedrooms, 4 beds, 2 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 16 reviews
Guest favourite
Home in Simpsonville
The Haven Simpsonville* Bourbon Trail* 3 bed/3bath
3 bedrooms, 3 queen beds, 3 bathrooms
11–16 Oct
4.98 out of 5 average rating, 40 reviews
Top guest favourite
Home in Shelbyville
HeatedPool~Sauna~ 2 HotTubs ~16 beds ~ Sleeps 25*
7 bedrooms, 16 beds, 4.5 bathrooms
17–22 Oct
5.0 out of 5 average rating, 22 reviews
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
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
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, 68 reviews
Guest favourite
Cabin in Waddy
Spacious Home, Sleeps 10, perfect for retreats
4 bedrooms, 6 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Shelbyville
Bourbon Trail*Hot Tub*Sauna*Mini Golf*Wi-Fi*EVSE
3 bedrooms, 4 beds, 2 bathrooms
30 Oct – 4 Nov
5.0 out of 5 average rating, 89 reviews
Top guest favourite
Cottage in Simpsonville
KY Cottage near Bourbon, Expo & Horse Park|Hot Tub
3 bedrooms, 4 beds, 2 bathrooms
15–20 Nov
5.0 out of 5 average rating, 69 reviews