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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
19–24 Jul
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4.99 out of 5 average rating, 623 reviews
Top guest favourite
Place to stay in Simpsonville
Private Lower Level King Bed/Farm View
2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
4.99 out of 5 average rating, 769 reviews
Top guest favourite
Home in Simpsonville
Luxury Country Retreat w 7 Bedroom | Bourbon Trail
5 bedrooms, 7 beds, 3.5 bathrooms
19–24 Jul
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Simpsonville
The Haven Simpsonville* Bourbon Trail* 3 bed/3bath
3 bedrooms, 3 queen beds, 3 bathrooms
18–23 Jul
4.97 out of 5 average rating, 36 reviews
Top guest favourite
Cottage in Simpsonville
KY Cottage near Bourbon, Expo & Horse Park|Hot Tub
3 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
5.0 out of 5 average rating, 59 reviews
Guest favourite
Home in Simpsonville
Eastern Sky
3 bedrooms, 3 beds, 2 bathrooms
19–24 Jul
4.94 out of 5 average rating, 36 reviews
Top guest favourite
Home in Simpsonville
Sleeps 24, Hot Tub, Sauna, Privacy on 5 acres
6 bedrooms, 14 beds, 4 bathrooms
19–24 Jul
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Rooms in Simpsonville
Slice Of Bourbon Country 2 BR FreshBreakfast
2 bedrooms, 2 beds, 1.5 bathrooms
19–24 Jul
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Farm stay in Simpsonville
Farm House - near Bourbon Trail & Pet Friendly
4 bedrooms, 4 beds, 1 bathroom
18–23 Jul
4.88 out of 5 average rating, 95 reviews
Top guest favourite
Flat in Simpsonville
Ridgecrest Estate. Comfort and Convenience.
1 king bed, 1 bathroom
18–23 Jul
4.98 out of 5 average rating, 141 reviews
Top guest favourite
Farm stay in Simpsonville
4BR Farm~Bourbon Trail~private heated pool~horses
4 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
5.0 out of 5 average rating, 51 reviews
Farm stay in Simpsonville
Restored 1919 Farmhouse on 100 Private Acres
4 bedrooms, 3 beds, 2 bathrooms
20–25 Jul
Guest favourite
Home in Shelbyville
Hitching Post on the Bourbon Trl
5 bedrooms, 6 beds, 3 bathrooms
18–23 Jul
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Louisville
The Persimmon Ridge Lodge - Golf Room & Pickleball
7 bedrooms, 9 beds, 5 bathrooms
1–6 Aug
4.98 out of 5 average rating, 91 reviews
Guest suite in Simpsonville
Simply Simpsonville
1 bedroom, 1 queen bed, 1 bathroom
9–14 Jul
Top guest favourite
Home in Shelbyville
Kentucky Estate: Speakeasy, Theater & Sleeps 20
8 bedrooms, 11 beds, 4.5 bathrooms
2–7 Aug
4.98 out of 5 average rating, 60 reviews
Top guest favourite
Home in Shelbyville
Bourbon, Bridles & Birdies Retreat
4 bedrooms, 7 beds, 2 bathrooms
17–22 Aug
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Home in Shelbyville
Historic Downtown~Heart of Bourbon Trail
3 bedrooms, 4 beds, 2.5 bathrooms
3–8 Aug
5.0 out of 5 average rating, 62 reviews
Superhost
Home in Shelbyville
Cozy Kentucky Winter, Bourbon Trail, Location!
2 bedrooms, 5 beds, 2.5 bathrooms
12–17 Jul
4.93 out of 5 average rating, 89 reviews