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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
11–16 Aug
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4.99 out of 5 average rating, 625 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, 777 reviews
Top guest favourite
Room in Simpsonville
A Slice Of Bourbon Country 1 BR *Fresh Breakfast*
1 king bed, 1.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 99 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, 65 reviews
Top guest favourite
Home in Simpsonville
Eastern Sky
3 bedrooms, 3 beds, 2 bathrooms
16–21 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
Top guest favourite
Flat in Simpsonville
Ridgecrest Estate. Comfort and Convenience.
1 king bed, 1 bathroom
12–17 Aug
4.98 out of 5 average rating, 141 reviews
Guest favourite
Home in Simpsonville
Luxury Country Retreat w 7 Bedroom | Bourbon Trail
7 bedrooms, 7 beds, 3.5 bathrooms
11–16 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
16–21 Aug
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Farm stay in Simpsonville
Farm House - near Bourbon Trail & Pet Friendly
4 bedrooms, 4 beds, 1 bathroom
15–20 Aug
4.89 out of 5 average rating, 101 reviews
Guest favourite
Farm stay in La Grange
The Cottage at StoneLedge 2 bedroom/1bath
2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
4.94 out of 5 average rating, 795 reviews
Farm stay in Simpsonville
Restored 1919 Farmhouse on 100 Private Acres
4 bedrooms, 3 beds, 2 bathrooms
12–17 Aug
Top 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, 99 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
Top guest favourite
Home in Louisville
"Call Me Old-Fashioned"in Derby & Bourbon Country!
3 bedrooms, 4 beds, 1 bathroom
13–18 Aug
4.99 out of 5 average rating, 251 reviews
Top guest favourite
Cabin in Mount Eden
Bourbon Country Cottage
2 bedrooms, 2 beds, 1 bathroom
12–17 Aug
4.97 out of 5 average rating, 188 reviews
Top guest favourite
Cabin in La Grange
The Log Cabin at StoneLedge
4 bedrooms, 7 beds, 2 bathrooms
22–27 Aug
4.97 out of 5 average rating, 134 reviews
Top guest favourite
Tiny home in La Grange
Brakeman's Cottage
1 bed, 1 bathroom
15–20 Aug
4.99 out of 5 average rating, 272 reviews