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Search results; Over 1,000 homes in Simpsonville

Top guest favourite
Place to stay in Simpsonville
Private Lower Level King Bed/Farm View
2 bedrooms, 2 beds, 1 private bathroom
11–16 Oct
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4.99 out of 5 average rating, 780 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
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
Top guest favourite
Room in Simpsonville
A Slice Of Bourbon Country 1 BR *Fresh Breakfast*
1 king bed, 1.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 101 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
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
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
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
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
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
Farm stay in Simpsonville
Restored 1919 Farmhouse on 100 Private Acres
4 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
Top guest favourite
Cabin in Louisville
Historically Registered 1847 Log Home
3 bedrooms, 6 beds, 2.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 79 reviews
Top guest favourite
Guest house in Shelbyville
Cottage of Eden. Bourbon Trail Stay in Shelby Co.
1 bedroom, 1 king bed, 1 bathroom
11–16 Sept
4.97 out of 5 average rating, 145 reviews
Cabin in Louisville
5 Acre Estate + Event Space w/ Hot Tub & Theater
5 bedrooms, 7 beds, 3.5 bathrooms
4–9 Oct
New place to stay
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
Cottage in Shelbyville
Hot Tub ~ Art Gallery ~ Bourbon Trail ~ KY Derby
3 bedrooms, 5 beds, 3 bathrooms
1–6 Sept
4.96 out of 5 average rating, 92 reviews
Room in Shelbyville
Near Weissinger Hills Golf Course + Free Breakfast
2 queen beds, 1 bathroom
1–6 Sept
New place to stay
Guest favourite
Camper van/Motorhome in Louisville
The Grace Airstream at Progress Park in Derby City
4 beds, 1 bathroom
7–12 Sept
4.97 out of 5 average rating, 342 reviews
Top guest favourite
Cabin in Lawrenceburg
Hidden View Cabin
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
4.99 out of 5 average rating, 130 reviews