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Search results; Over 1,000 homes in Simpsonville

Top guest favourite
Flat in Simpsonville
Ridgecrest Estate. Comfort and Convenience.
Studio, 1 bed, 1 private bathroom
21–26 Jul
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4.98 out of 5 average rating, 141 reviews
Top guest favourite
Place to stay in Simpsonville
Private Lower Level King Bed/Farm View
4.99 out of 5 average rating, 771 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
Guest favourite
Home in Simpsonville
Luxury Country Retreat w 7 Bedroom | Bourbon Trail
5.0 out of 5 average rating, 6 reviews, 7 bedrooms, 7 beds, 3.5 bathrooms
26–31 Jul
Top guest favourite
Room in Simpsonville
Sky Blue Ensuite has a King bed & balcony.
4.99 out of 5 average rating, 623 reviews, 1 king bed, 1 bathroom
20–25 Jul
Guest favourite
Home in Simpsonville
Eastern Sky
4.95 out of 5 average rating, 38 reviews, 3 bedrooms, 3 beds, 2 bathrooms
21–26 Jul
Top guest favourite
Cottage in Simpsonville
KY Cottage near Bourbon, Expo & Horse Park|Hot Tub
5.0 out of 5 average rating, 61 reviews, 3 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
Top guest favourite
Rooms in Simpsonville
Slice Of Bourbon Country 2 BR FreshBreakfast
5.0 out of 5 average rating, 51 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
14–19 Aug
Guest favourite
Home in Simpsonville
The Haven Simpsonville* Bourbon Trail* 3 bed/3bath
4.97 out of 5 average rating, 36 reviews, 3 bedrooms, 3 beds, 3 bathrooms
31 Jul – 5 Aug
Top guest favourite
Farm stay in Simpsonville
4BR Farm~Bourbon Trail~private heated pool~horses
5.0 out of 5 average rating, 52 reviews, 4 bedrooms, 4 beds, 3 bathrooms
8–13 Sept
Top guest favourite
Farm stay in Simpsonville
Farm House - near Bourbon Trail & Pet Friendly
4.89 out of 5 average rating, 96 reviews, 4 bedrooms, 4 beds, 1 bathroom
9–14 Aug
Top guest favourite
Home in Simpsonville
Sleeps 24, Hot Tub, Sauna, Privacy on 5 acres
5.0 out of 5 average rating, 12 reviews, 6 bedrooms, 14 beds, 4 bathrooms
20–25 Jul
Farm stay in Simpsonville
Restored 1919 Farmhouse on 100 Private Acres
4 bedrooms, 3 beds, 2 bathrooms
20–25 Jul
Top guest favourite
Home in Shelbyville
Jeptha Crest-Bourbon Trail, Hot Tub, Sauna, Dog OK
5.0 out of 5 average rating, 26 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
26–31 Jul
Top guest favourite
Guest house in Shelbyville
Cottage of Eden. Bourbon Trail Stay in Shelby Co.
4.97 out of 5 average rating, 142 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
Top guest favourite
Home in Shelbyville
Historic Downtown~Heart of Bourbon Trail
5.0 out of 5 average rating, 62 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
3–8 Aug
Top guest favourite
Home in Shelbyville
The Hutch on Hardesty
5.0 out of 5 average rating, 23 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Home in Finchville
Country Retreat on Bourbon Trail - Fire Pit - King
5.0 out of 5 average rating, 88 reviews, 2 bedrooms, 2 beds, 1 bathroom
18–23 Aug
Home in Shelbyville
Long Ridge Farm
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Jul
Top guest favourite
Room in Louisville
The Yellow Horse Room / King bed & Futon
4.98 out of 5 average rating, 435 reviews, 1 king bed, 1.5 bathrooms
2–7 Aug