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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
28 Sept – 3 Oct
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4.99 out of 5 average rating, 629 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, 785 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, 8 reviews
Top guest favourite
Room in Simpsonville
A Slice Of Bourbon Country 1 BR *Fresh Breakfast*
1 king bed, 1.5 bathrooms
17–22 Oct
5.0 out of 5 average rating, 105 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
Flat in Simpsonville
Ridgecrest Estate. Comfort and Convenience.
1 king bed, 1 bathroom
10–15 Sept
4.98 out of 5 average rating, 141 reviews
Top guest favourite
Home in Simpsonville
Eastern Sky
3 bedrooms, 3 beds, 2 bathrooms
5–10 Oct
4.96 out of 5 average rating, 45 reviews
Top guest favourite
Farm stay in Simpsonville
4BR Farm~Bourbon Trail~private heated pool~horses
4 bedrooms, 4 beds, 3 bathrooms
10–15 Sept
5.0 out of 5 average rating, 57 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, 40 reviews
Top guest favourite
Cabin in Louisville
Historically Registered 1847 Log Home
3 bedrooms, 6 beds, 2.5 bathrooms
9–14 Sept
5.0 out of 5 average rating, 80 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, 24 reviews
Home in Shelbyville
Long Ridge Farm
3 bedrooms, 4 beds, 2.5 bathrooms
9–14 Sept
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
Top guest favourite
Loft in Shelbyville
The Stick at Pondview
3 bedrooms, 4 beds, 1 bathroom
18–23 Oct
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Barn in Louisville
Luxury modern barn home on a Kentucky horse farm
3 bedrooms, 4 beds, 1 bathroom
10–15 Sept
5.0 out of 5 average rating, 21 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
Guest favourite
Home in Shelbyville
Hitching Post on the Bourbon Trl
5 bedrooms, 6 beds, 3 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 12 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