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Guest favorite
Private room in Simpsonville
Sky Blue Ensuite has a King bed & balcony.
2 guests1 bedroom1 bed1 private bath
May 4 – 9
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May 4 – 9
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ﺩ.ﺇ3,099 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
May 4 – 9
ﺩ.ﺇ2,174 for 5 nights
for 5 nights
4.98 out of 5 average rating, 650 reviews
Guest favorite
Home in Simpsonville
Comfortable sleek home bourbon trail
Free cancellation
May 10 – 15
ﺩ.ﺇ4,082 for 5 nights
for 5 nights
4.94 out of 5 average rating, 108 reviews
Home in Simpsonville
The Haven Simpsonville* Bourbon Trail* 3 bed/3bath
Free cancellation
May 4 – 9
ﺩ.ﺇ5,850 for 5 nights
for 5 nights
5.0 out of 5 average rating, 3 reviews
Guest favorite
Home in Simpsonville
Derby Bourbon Trail Classic
Free cancellation
May 11 – 16
ﺩ.ﺇ4,628 for 5 nights
for 5 nights
4.9 out of 5 average rating, 31 reviews
Top guest favorite
Cottage in Simpsonville
Miles Around KY Cottage-Hot Tub
4 beds
Jun 9 – 14
ﺩ.ﺇ4,759 for 5 nights
for 5 nights
5.0 out of 5 average rating, 29 reviews
Guest favorite
Home in Simpsonville
Charming 4 Bedroom classic home bourbon trail!
4 beds
May 4 – 9
ﺩ.ﺇ9,837 for 5 nights
for 5 nights
4.87 out of 5 average rating, 147 reviews
Top guest favorite
Room in Simpsonville
Stay with AmyCulinary teacher,
A Slice Of Bourbon Country 1 BR *Fresh Breakfast*
May 4 – 9
ﺩ.ﺇ1,899 for 5 nights
for 5 nights
5.0 out of 5 average rating, 48 reviews
Top guest favorite
Home in Simpsonville
Sleeps 24, 6BR, 4BA, Hot Tub
Free cancellation
Jun 8 – 13
ﺩ.ﺇ22,256 for 5 nights
for 5 nights
4.95 out of 5 average rating, 64 reviews
Guest favorite
Farm stay in Simpsonville
Spacious Home with Beautiful Views
4 beds
May 10 – 15
ﺩ.ﺇ3,621 for 5 nights
for 5 nights
4.91 out of 5 average rating, 64 reviews
Top guest favorite
Farm stay in Shelbyville
Cozy Retreat at Red Gate Farm
1 queen bed
May 5 – 10
ﺩ.ﺇ2,499 for 5 nights
for 5 nights
4.98 out of 5 average rating, 56 reviews
Top guest favorite
Farm stay in Simpsonville
Farm House - near Bourbon Trail & Pet Friendly
Free cancellation
May 12 – 17
ﺩ.ﺇ3,659 for 5 nights
for 5 nights
4.87 out of 5 average rating, 70 reviews
Guest favorite
Home in Simpsonville
*Distilleries close by* Hot tub*Firepit
3 beds
May 31 – Jun 5
ﺩ.ﺇ8,235 for 5 nights
for 5 nights
4.95 out of 5 average rating, 19 reviews
Top guest favorite
Farm stay in Simpsonville
4BR Farm~Bourbon Trail~private pool~horses
4 beds
May 4 – 9
ﺩ.ﺇ9,807 for 5 nights
for 5 nights
5.0 out of 5 average rating, 22 reviews
Top guest favorite
Home in Finchville
Country Retreat on Bourbon Trail - Fire Pit - King
Free cancellation
May 5 – 10
ﺩ.ﺇ4,292 for 5 nights
for 5 nights
5.0 out of 5 average rating, 30 reviews
Superhost
Home in Shelbyville
Charming Home in Historic Downtown Shelbyville
3 beds
May 11 – 16
ﺩ.ﺇ1,959 for 5 nights
for 5 nights
4.7 out of 5 average rating, 10 reviews
Guest favorite
Home in Simpsonville
Eastern Sky
Free cancellation
May 1 – 6
ﺩ.ﺇ6,272 for 5 nights
for 5 nights
4.8 out of 5 average rating, 5 reviews
Top guest favorite
Cabin in Louisville
Historic Cabin by Bourbon Trail
Free cancellation
May 17 – 22
ﺩ.ﺇ4,043 for 5 nights
for 5 nights
5.0 out of 5 average rating, 201 reviews
Guest suite in Louisville
PGA Perfect stay- 2 miles away
Free cancellation
May 4 – 9
ﺩ.ﺇ2,023 for 5 nights
for 5 nights
4.71 out of 5 average rating, 14 reviews