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Search results; Over 1,000 homes in Simpsonville

Top guest favourite
Farm stay in Simpsonville
Farm House - near Bourbon Trail & Pet Friendly
4 bedrooms, 4 beds, 1 shared bathroom
18–23 Aug
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4.89 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
A Slice Of Bourbon Country 1 BR *Fresh Breakfast*
1 king bed, 1.5 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 99 reviews
Top guest favourite
Room in Simpsonville
Sky Blue Ensuite has a King bed & balcony.
1 king bed, 1 bathroom
17–22 Aug
4.99 out of 5 average rating, 625 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, 67 reviews
Top guest favourite
Flat in Simpsonville
Ridgecrest Estate. Comfort and Convenience.
1 king bed, 1 bathroom
18–23 Aug
4.98 out of 5 average rating, 141 reviews
Top guest favourite
Home in Simpsonville
Eastern Sky
3 bedrooms, 3 beds, 2 bathrooms
18–23 Aug
4.95 out of 5 average rating, 42 reviews
Guest favourite
Home in Simpsonville
The Haven Simpsonville* Bourbon Trail* 3 bed/3bath
3 bedrooms, 3 queen beds, 3 bathrooms
22–27 Aug
4.98 out of 5 average rating, 40 reviews
Guest favourite
Home in Simpsonville
Luxury Country Retreat w 7 Bedroom | Bourbon Trail
7 bedrooms, 7 beds, 3.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 8 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, 55 reviews
Top guest favourite
Home in Simpsonville
Sleeps 26, Hot Tub & Sauna - Near Bourbon Trail
6 bedrooms, 14 beds, 4 bathrooms
17–22 Aug
5.0 out of 5 average rating, 14 reviews
Guest favourite
Loft in Shelbyville
The Lucky Penny Downtown Loft - Central Location!
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
4.92 out of 5 average rating, 50 reviews
Guest favourite
Room in Jeffersonville
Zen Garden Retreat • Queen Bed • Private Room
1 double bed, 1 bathroom
22–27 Oct
4.92 out of 5 average rating, 834 reviews
Guest favourite
Flat in Prospect
Exclusive Farmhouse w/ a Romantic Garden View!
1 bedroom, 2 single beds, 1 bathroom
27 Aug – 1 Sept
4.87 out of 5 average rating, 94 reviews
Top guest favourite
Home in Louisville
"Call Me Old-Fashioned"in Derby & Bourbon Country!
3 bedrooms, 4 beds, 1 bathroom
30 Aug – 4 Sept
4.99 out of 5 average rating, 254 reviews
Guest favourite
Home in Shelbyville
Lake Escape | Fire Pit, Fishing & Bourbon Trail
1 bedroom, 1 queen bed, 1.5 bathrooms
21–26 Aug
4.9 out of 5 average rating, 101 reviews
Farm stay in Simpsonville
Restored 1919 Farmhouse on 100 Private Acres
4 bedrooms, 3 beds, 2 bathrooms
18–23 Aug
Guest favourite
Home in Shelbyville
The Hutch on Hardesty
1 bedroom, 2 beds, 1 bathroom
17–22 Aug
4.96 out of 5 average rating, 27 reviews
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, 21 reviews