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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
18–23 Jul
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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
4.99 out of 5 average rating, 769 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Room in Simpsonville
Sky Blue Ensuite has a King bed & balcony.
4.99 out of 5 average rating, 623 reviews, 1 king bed, 1 bathroom
19–24 Jul
Top guest favourite
Rooms in Simpsonville
Slice Of Bourbon Country 2 BR FreshBreakfast
5.0 out of 5 average rating, 50 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
19–24 Jul
Top guest favourite
Home in Simpsonville
Luxury Country Retreat w 7 Bedroom | Bourbon Trail
5.0 out of 5 average rating, 5 reviews, 5 bedrooms, 7 beds, 3.5 bathrooms
19–24 Jul
Top guest favourite
Cottage in Simpsonville
KY Cottage near Bourbon, Expo & Horse Park|Hot Tub
5.0 out of 5 average rating, 59 reviews, 3 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
Guest favourite
Home in Simpsonville
Eastern Sky
4.95 out of 5 average rating, 37 reviews, 3 bedrooms, 3 beds, 2 bathrooms
21–26 Jul
Guest favourite
Home in Simpsonville
The Haven Simpsonville* Bourbon Trail* 3 bed/3bath
4.97 out of 5 average rating, 36 reviews, 3 bedrooms, 3 beds, 3 bathrooms
31 Jul – 5 Aug
Top guest favourite
Loft in Shelbyville
The Stick at Pondview
5.0 out of 5 average rating, 17 reviews, 3 bedrooms, 4 beds, 1 bathroom
19–24 Jul
Top guest favourite
Farm stay in Simpsonville
Farm House - near Bourbon Trail & Pet Friendly
4.88 out of 5 average rating, 95 reviews, 4 bedrooms, 4 beds, 1 bathroom
18–23 Jul
Top guest favourite
Home in Simpsonville
Sleeps 24, Hot Tub, Sauna, Privacy on 5 acres
5.0 out of 5 average rating, 12 reviews, 6 bedrooms, 14 beds, 4 bathrooms
19–24 Jul
Top guest favourite
Flat in Shelbyville
Unique Downtown Studio with an Industrial Vibe
4.97 out of 5 average rating, 139 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Home in Shelbyville
Long Ridge Farm
3 bedrooms, 4 beds, 2.5 bathrooms
12–17 Jul
Top guest favourite
Home in Shelbyville
Bourbon, Bridles & Birdies Retreat
5.0 out of 5 average rating, 16 reviews, 4 bedrooms, 7 beds, 2 bathrooms
17–22 Aug
Top guest favourite
Farm stay in Shelbyville
Cozy Retreat at Red Gate Farm
4.99 out of 5 average rating, 94 reviews, 1 bedroom, 1 bed, 1 bathroom
20–25 Jul
Guest favourite
Cottage in Shelbyville
Hot Tub ~ Art Gallery ~ Bourbon Trail ~ KY Derby
4.95 out of 5 average rating, 88 reviews, 3 bedrooms, 5 beds, 3 bathrooms
9–14 Aug
Guest favourite
Farm stay in Shelbyville
Horse &Hound Bourbon Trail Retreat@Chickapoo Farm
5.0 out of 5 average rating, 16 reviews, 3 bedrooms, 4 beds, 2 bathrooms
12–17 Jul
Home in Shelbyville
Bourbon Trail Farmhouse | Hot Tub + Fenced Yard
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 4 beds, 2 bathrooms
20–25 Jul
Top guest favourite
Farm stay in Simpsonville
4BR Farm~Bourbon Trail~private heated pool~horses
5.0 out of 5 average rating, 51 reviews, 4 bedrooms, 4 beds, 3 bathrooms
24–29 Aug