filters

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
8–13 Sept
,
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
4.99 out of 5 average rating, 784 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, 104 reviews
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
Sky Blue Ensuite has a King bed & balcony.
1 king bed, 1 bathroom
28 Sept – 3 Oct
4.99 out of 5 average rating, 627 reviews
Top guest favourite
Flat in Simpsonville
Ridgecrest Estate. Comfort and Convenience.
1 king bed, 1 bathroom
7–12 Sept
4.98 out of 5 average rating, 141 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, 68 reviews
Guest favourite
Home in Simpsonville
The Haven Simpsonville* Bourbon Trail* 3 bed/3bath
3 bedrooms, 3 queen beds, 3 bathrooms
7–12 Sept
4.98 out of 5 average rating, 40 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, 44 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
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, 80 reviews
Top guest favourite
Farm stay in Louisville
Gentleman’s Farm CEORetreat, Bourbon Trail, In-Cty
6 bedrooms, 15 beds, 3.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 39 reviews
Guest favourite
Loft in Shelbyville
The Lucky Penny Downtown Loft - Central Location!
1 bedroom, 2 beds, 1 bathroom
12–17 Sept
4.91 out of 5 average rating, 53 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
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
Superhost
Home in Shelbyville
Cozy Kentucky Winter, Bourbon Trail, Location!
2 bedrooms, 5 beds, 2.5 bathrooms
12–17 Oct
4.9 out of 5 average rating, 93 reviews
Guest favourite
Cottage in Shelbyville
Hot Tub ~ Art Gallery ~ Bourbon Trail ~ KY Derby
3 bedrooms, 5 beds, 3 bathrooms
8–13 Nov
4.96 out of 5 average rating, 92 reviews
Home in Shelbyville
Long Ridge Farm
3 bedrooms, 4 beds, 2.5 bathrooms
7–12 Sept
Guest favourite
Home in Louisville
Red Bridge Retreat
4 bedrooms, 4 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 34 reviews