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Guest favorite
Farm stay in Simpsonville
4BR Farm~Bourbon Trail~private pool~horses
8 guests4 bedrooms4 beds3 baths
Sep 29 – Oct 4
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Sep 29 – Oct 4
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R50,222 ZAR for 5 nights
for 5 nights

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Top guest favorite
Place to stay in Simpsonville
Private Lower Level King Bed/Patio
Free cancellation
Jun 21 – 26
R10,911 ZAR for 5 nights
for 5 nights
4.98 out of 5 average rating, 661 reviews
Guest favorite
Home in Simpsonville
The Haven Simpsonville* Bourbon Trail* 3 bed/3bath
Free cancellation
Jun 11 – 16
R23,367 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 10 reviews
Top guest favorite
Room in Simpsonville
Stay with AmyCulinary teacher,
A Slice Of Bourbon Country 1 BR *Fresh Breakfast*
Jun 15 – 20
R9,326 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 55 reviews
Guest favorite
Home in Simpsonville
Eastern Sky
Free cancellation
Jun 15 – 20
R15,754 ZAR for 5 nights
for 5 nights
4.91 out of 5 average rating, 11 reviews
Guest favorite
Home in Simpsonville
Charming 4 Bedroom classic home bourbon trail!
4 beds
Jun 9 – 14
R20,723 ZAR for 5 nights
for 5 nights
4.87 out of 5 average rating, 151 reviews
Top guest favorite
Room in Simpsonville
Stay with DianaRetired,
Sky Blue Ensuite has a King bed & balcony.
Jun 8 – 13
R12,687 ZAR for 5 nights
for 5 nights
4.99 out of 5 average rating, 574 reviews
Guest favorite
Home in Simpsonville
Comfortable sleek home bourbon trail
4 beds
Jun 10 – 15
R21,547 ZAR for 5 nights
for 5 nights
4.95 out of 5 average rating, 112 reviews
Top guest favorite
Cottage in Simpsonville
Miles Around KY Cottage-Hot Tub
4 beds
Jun 10 – 15
R24,318 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 34 reviews
Top guest favorite
Home in Simpsonville
Sleeps 24, 6BR, 4BA, Hot Tub
Free cancellation
Jun 13 – 18
R68,598 ZAR for 5 nights
for 5 nights
4.95 out of 5 average rating, 66 reviews
Guest favorite
Home in Simpsonville
Derby Bourbon Trail Classic
Jun 14 – 19
R22,732 ZAR for 5 nights
for 5 nights
4.89 out of 5 average rating, 35 reviews
Guest favorite
Home in Simpsonville
*Distilleries close by* Hot tub*Firepit
3 beds
Jul 5 – 10
R35,525 ZAR for 5 nights
for 5 nights
4.96 out of 5 average rating, 23 reviews
Guest favorite
Farm stay in Simpsonville
Spacious Home with Beautiful Views
4 beds
Jun 22 – 27
R15,994 ZAR for 5 nights
for 5 nights
4.9 out of 5 average rating, 68 reviews
Top guest favorite
Home in Finchville
Country Retreat on Bourbon Trail - Fire Pit - King
Free cancellation
Jun 15 – 20
R17,403 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 38 reviews
Top guest favorite
Cottage in Shelbyville
Cozy Cottage on Firefly Farm
Free cancellation
Jul 14 – 19
R10,256 ZAR for 5 nights
for 5 nights
4.94 out of 5 average rating, 208 reviews
Top guest favorite
Farm stay in Shelbyville
Cozy Retreat at Red Gate Farm
1 queen bed
Jul 1 – 6
R13,619 ZAR for 5 nights
for 5 nights
4.98 out of 5 average rating, 58 reviews
Guest favorite
Home in Shelbyville
Shelbyville, KY - Bourbon Trail and Horse Country.
4 queen beds
Jun 9 – 14
R27,067 ZAR for 5 nights
for 5 nights
4.93 out of 5 average rating, 14 reviews
Top guest favorite
Room in Louisville
Stay with Harriette. a retired teacher,
Large room with bath in quiet neighborhood
Jun 25 – 30
R5,857 ZAR for 5 nights
for 5 nights
4.96 out of 5 average rating, 1400 reviews
Superhost
Home in Shelbyville
Ideal for Mid-Term: 3-Bed w/ fin bsmt on 1+ acre
3 beds
Jun 8 – 13
R31,719 ZAR for 5 nights
for 5 nights