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Search results; Over 1,000 homes in Shelbyville

Guest favourite
Farm stay in Shelbyville
Horse &Hound Bourbon Trail Retreat@Chickapoo Farm
3 bedrooms, 4 beds, 2 private bathrooms
5–10 Sept
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5.0 out of 5 average rating, 16 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
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
Guest favourite
Loft in Shelbyville
Sleeps 16/near everything-Transportation available
5 bedrooms, 7 beds, 3.5 bathrooms
5–10 Sept
4.99 out of 5 average rating, 142 reviews
Superhost
Home in Shelbyville
the bourbon barrel escape HotTub Game Room
4 bedrooms, 5 beds, 3 bathrooms
7–12 Sept
New place to stay
Top guest favourite
Home in Shelbyville
Bourbon, Bridles & Birdies Retreat
4 bedrooms, 7 beds, 2 bathrooms
7–12 Dec
5.0 out of 5 average rating, 23 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, 145 reviews
Top guest favourite
Home in Shelbyville
Parris on Main St - Downtown, Bourbon and Derby!
3 bedrooms, 4 beds, 2.5 bathrooms
30 Dec – 4 Jan
4.96 out of 5 average rating, 27 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
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
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, 44 reviews
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
Top guest favourite
Home in Shelbyville
Historic Downtown~Heart of Bourbon Trail
3 bedrooms, 4 beds, 2.5 bathrooms
9–14 Nov
5.0 out of 5 average rating, 65 reviews
Guest favourite
Loft in Shelbyville
Close to all the popular distilleries Perfect Spot
2 bedrooms, 2 beds, 2 bathrooms
8–13 Sept
4.98 out of 5 average rating, 113 reviews
Top guest favourite
Home in Shelbyville
High Rollers' Retreat w/pool and Pond
8 bedrooms, 8 beds, 7.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 16 reviews
Guest favourite
Home in Shelbyville
Bourbon Trail Retreat: Pool, Hot tub & Game Room
4 bedrooms, 4 beds, 2.5 bathrooms
28 Sept – 3 Oct
4.92 out of 5 average rating, 13 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
Guest favourite
Loft in Shelbyville
The Lucky Penny Downtown Loft - Central Location!
1 bedroom, 2 beds, 1 bathroom
12–17 Sept
4.91 out of 5 average rating, 53 reviews
Top guest favourite
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, 38 reviews