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Search results; Over 1,000 homes in Simpsonville

Top guest favourite
Room in Simpsonville
Sky Blue Ensuite has a King bed & balcony.
1 bedroom, 1 bed, 1 private bathroom
19–24 Jul
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4.99 out of 5 average rating, 623 reviews
Top guest favourite
Home in Simpsonville
Luxury Country Retreat w 7 Bedroom | Bourbon Trail
5 bedrooms, 7 beds, 3.5 bathrooms
3–8 Jul
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Place to stay in Simpsonville
Private Lower Level King Bed/Farm View
2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
4.99 out of 5 average rating, 767 reviews
Top guest favourite
Cottage in Simpsonville
KY Cottage near Bourbon, Expo & Horse Park|Hot Tub
3 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
5.0 out of 5 average rating, 59 reviews
Guest favourite
Home in Simpsonville
Eastern Sky
3 bedrooms, 3 beds, 2 bathrooms
19–24 Jul
4.94 out of 5 average rating, 36 reviews
Guest favourite
Home in Simpsonville
The Haven Simpsonville* Bourbon Trail* 3 bed/3bath
3 bedrooms, 3 queen beds, 3 bathrooms
3–8 Jul
4.97 out of 5 average rating, 36 reviews
Top guest favourite
Rooms in Simpsonville
Slice Of Bourbon Country 2 BR FreshBreakfast
2 bedrooms, 2 beds, 1.5 bathrooms
19–24 Jul
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Flat in Simpsonville
Ridgecrest Estate. Comfort and Convenience.
1 king bed, 1 bathroom
18–23 Jul
4.98 out of 5 average rating, 141 reviews
Top guest favourite
Home in Simpsonville
Sleeps 24, Hot Tub, Sauna, Privacy on 5 acres
6 bedrooms, 14 beds, 4 bathrooms
3–8 Jul
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Farm stay in Simpsonville
Farm House - near Bourbon Trail & Pet Friendly
4 bedrooms, 4 beds, 1 bathroom
11–16 Jul
4.88 out of 5 average rating, 92 reviews
Top guest favourite
Farm stay in Simpsonville
4BR Farm~Bourbon Trail~private heated pool~horses
4 bedrooms, 4 beds, 3 bathrooms
8–13 Sept
5.0 out of 5 average rating, 50 reviews
Top guest favourite
Home in Shelbyville
Parris on Main St - Downtown, Bourbon and Derby!
3 bedrooms, 4 beds, 2.5 bathrooms
5–10 Jul
4.96 out of 5 average rating, 23 reviews
Top guest favourite
Farm stay in Shelbyville
Cozy Retreat at Red Gate Farm
1 bedroom, 1 queen bed, 1 bathroom
13–18 Jul
4.99 out of 5 average rating, 94 reviews
Top guest favourite
Guest house in Shelbyville
Cottage of Eden. Bourbon Trail Stay in Shelby Co.
1 bedroom, 1 king bed, 1 bathroom
5–10 Jul
4.97 out of 5 average rating, 139 reviews
Farm stay in Simpsonville
Restored 1919 Farmhouse on 100 Private Acres
4 bedrooms, 3 beds, 2 bathrooms
4–9 Jul
Home in Shelbyville
Bourbon Trail Farmhouse | Hot Tub + Fenced Yard
3 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
New place to stay
Top guest favourite
Home in Louisville
Entire House in Middletown - Trailers/RVs access
3 bedrooms, 3 queen beds, 2.5 bathrooms
12–17 Jul
4.96 out of 5 average rating, 51 reviews
Top guest favourite
Home in Pleasureville
Bourbon Trail Country Getaway
3 bedrooms, 4 beds, 2 bathrooms
3–8 Aug
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Home in Shelbyville
The Hutch on Hardesty
1 bedroom, 2 beds, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 20 reviews