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Search results; Over 1,000 homes in Simpsonville

Top guest favourite
Flat in Simpsonville
Ridgecrest Estate. Comfort and Convenience.
Studio, 1 bed, 1 private bathroom
16–21 Aug
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4.98 out of 5 average rating, 141 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, 779 reviews
Top guest favourite
Room in Simpsonville
Sky Blue Ensuite has a King bed & balcony.
1 king bed, 1 bathroom
15–20 Aug
4.99 out of 5 average rating, 625 reviews
Guest favourite
Home in Simpsonville
Luxury Country Retreat w 7 Bedroom | Bourbon Trail
7 bedrooms, 7 beds, 3.5 bathrooms
15–20 Aug
5.0 out of 5 average rating, 8 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
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, 66 reviews
Top guest favourite
Rooms in Simpsonville
Slice Of Bourbon Country 2 BR FreshBreakfast
2 bedrooms, 2 beds, 1.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 53 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
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
Farm stay in Simpsonville
Farm House - near Bourbon Trail & Pet Friendly
4 bedrooms, 4 beds, 1 bathroom
18–23 Aug
4.89 out of 5 average rating, 101 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
Farm stay in Simpsonville
Restored 1919 Farmhouse on 100 Private Acres
4 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
Top guest favourite
Home in Louisville
Entire House in Middletown - Trailers/RVs access
3 bedrooms, 3 queen beds, 2.5 bathrooms
16–21 Aug
4.96 out of 5 average rating, 53 reviews
Guest favourite
Cottage in Shelbyville
Hot Tub ~ Art Gallery ~ Bourbon Trail ~ KY Derby
3 bedrooms, 5 beds, 3 bathrooms
16–21 Aug
4.96 out of 5 average rating, 92 reviews
Cabin in Louisville
5 Acre Estate + Event Space w/ Hot Tub & Theater
5 bedrooms, 7 beds, 3.5 bathrooms
23–28 Aug
New place to stay
Room in Shelbyville
Near Weissinger Hills Golf Course + Free Breakfast
2 queen beds, 1 bathroom
16–21 Aug
New place to stay
Guest favourite
Home in Shelbyville
Bourbon Trail Farmhouse | Hot Tub + Fenced Yard
3 bedrooms, 4 beds, 2 bathrooms
17–22 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Camper van/Motorhome in Louisville
The GiGi Airstream, Lakeside at Progress Park
1 bedroom, 5 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 161 reviews
Top guest favourite
Farm stay in Shelbyville
Cozy Retreat at Red Gate Farm
1 bedroom, 1 queen bed, 1 bathroom
15–20 Aug
4.99 out of 5 average rating, 99 reviews