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Search results; Over 1,000 homes in Simpsonville

Top guest favourite
Farm stay in Simpsonville
4BR Farm~Bourbon Trail~private heated pool~horses
4 bedrooms, 4 beds, 3 private bathrooms
10–15 Oct
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5.0 out of 5 average rating, 57 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
4.98 out of 5 average rating, 787 reviews
Home in Simpsonville
Spacious Bourbon retreat near Downtown Louisville!
5 bedrooms, 6 beds, 2 bathrooms
28 Sept – 3 Oct
New place to stay
Guest favourite
Home in Simpsonville
Luxury Country Retreat w 7 Bedroom | Bourbon Trail
7 bedrooms, 7 beds, 3.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Simpsonville
The Haven Simpsonville* Bourbon Trail* 3 bed/3bath
3 bedrooms, 3 queen beds, 3 bathrooms
11–16 Oct
4.98 out of 5 average rating, 41 reviews
Top guest favourite
Cottage in Simpsonville
KY Cottage near Bourbon, Expo & Horse Park|Hot Tub
3 bedrooms, 4 beds, 2 bathrooms
15–20 Nov
5.0 out of 5 average rating, 69 reviews
Top guest favourite
Rooms in Simpsonville
Slice Of Bourbon Country 2 BR FreshBreakfast
2 bedrooms, 2 beds, 1.5 bathrooms
17–22 Oct
5.0 out of 5 average rating, 54 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, 16 reviews
Top guest favourite
Home in Simpsonville
Eastern Sky
3 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
4.96 out of 5 average rating, 45 reviews
Top guest favourite
Room in Simpsonville
Sky Blue Ensuite has a King bed & balcony.
1 king bed, 1 bathroom
28 Sept – 3 Oct
4.99 out of 5 average rating, 629 reviews
Top guest favourite
Flat in Simpsonville
Ridgecrest Estate. Comfort and Convenience.
1 king bed, 1 bathroom
9–14 Oct
4.98 out of 5 average rating, 142 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, 102 reviews
Farm stay in Simpsonville
Restored 1919 Farmhouse on 100 Private Acres
4 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
Top guest favourite
Home in Shelbyville
Kentucky Estate: Speakeasy, Theater & Sleeps 20
8 bedrooms, 11 beds, 4.5 bathrooms
15–20 Sept
4.99 out of 5 average rating, 68 reviews
Top guest favourite
Home in Louisville
Unique Serenity - Entire Home On Private 3-Acres
4 bedrooms, 6 beds, 4 bathrooms
12–17 Oct
5.0 out of 5 average rating, 64 reviews
Guest favourite
Farm stay in Simpsonville
Horse Farm with Beautiful Views
2 bedrooms, 4 beds, 2.5 bathrooms
4–9 May
4.89 out of 5 average rating, 80 reviews
Top guest favourite
Home in Shelbyville
Historic Downtown~Heart of Bourbon Trail
3 bedrooms, 4 beds, 2.5 bathrooms
9–14 Nov
5.0 out of 5 average rating, 66 reviews
Top guest favourite
Home in Louisville
Entire House in Middletown - Trailers/RVs access
3 bedrooms, 3 queen beds, 2.5 bathrooms
28 Sept – 3 Oct
4.96 out of 5 average rating, 54 reviews
Top guest favourite
Home in Louisville
Newly Renovated Derby House
3 bedrooms, 3 queen beds, 2 bathrooms
5–10 Oct
4.99 out of 5 average rating, 219 reviews