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Search results; Over 1,000 homes in Simpsonville

Top guest favourite
Room in Simpsonville
A Slice Of Bourbon Country 1 BR *Fresh Breakfast*
1 bedroom, 1 bed, 1.5 private bathrooms
1–6 Sept
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5.0 out of 5 average rating, 101 reviews
Top guest favourite
Place to stay in Simpsonville
Private Lower Level King Bed/Farm View
2 bedrooms, 2 beds, 1 bathroom
11–16 Oct
4.99 out of 5 average rating, 780 reviews
Top guest favourite
Room in Simpsonville
Sky Blue Ensuite has a King bed & balcony.
1 king bed, 1 bathroom
1–6 Sept
4.99 out of 5 average rating, 625 reviews
Guest favourite
Home in Simpsonville
The Haven Simpsonville* Bourbon Trail* 3 bed/3bath
3 bedrooms, 3 queen beds, 3 bathrooms
6–11 Sept
4.98 out of 5 average rating, 40 reviews
Top guest favourite
Cottage in Simpsonville
KY Cottage near Bourbon, Expo & Horse Park|Hot Tub
3 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
5.0 out of 5 average rating, 68 reviews
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
Top guest favourite
Flat in Simpsonville
Ridgecrest Estate. Comfort and Convenience.
1 king bed, 1 bathroom
6–11 Sept
4.98 out of 5 average rating, 141 reviews
Top guest favourite
Home in Simpsonville
Eastern Sky
3 bedrooms, 3 beds, 2 bathrooms
5–10 Oct
4.95 out of 5 average rating, 43 reviews
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
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, 56 reviews
Farm stay in Simpsonville
Restored 1919 Farmhouse on 100 Private Acres
4 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
Top guest favourite
Flat in Simpsonville
Barn Apartment Getaway near Louisville
2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Farm stay in Simpsonville
Farm House - near Bourbon Trail & Pet Friendly
4 bedrooms, 4 beds, 1 bathroom
12–17 Dec
4.89 out of 5 average rating, 101 reviews
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, 78 reviews
Room in Shelbyville
Near Weissinger Hills Golf Course + Free Breakfast
2 queen beds, 1 bathroom
1–6 Sept
New place to stay
Top guest favourite
Home in Crestwood
Briar Creek Cottage
2 bedrooms, 2 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 92 reviews
Top guest favourite
Home in Shelbyville
The Hutch on Hardesty
1 bedroom, 2 beds, 1 bathroom
6–11 Sept
4.96 out of 5 average rating, 27 reviews
Guest favourite
Room in Jeffersonville
Zen Garden Retreat • Queen Bed • Private Room
1 double bed, 1 bathroom
10–15 Sept
4.92 out of 5 average rating, 834 reviews
Top guest favourite
Home in Finchville
Country Retreat on Bourbon Trail - Fire Pit - King
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 91 reviews