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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 15 – 20
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May 15 – 20
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ﺩ.ﺇ2,583 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 10 – 15
ﺩ.ﺇ1,894 for 5 nights
for 5 nights
4.98 out of 5 average rating, 656 reviews
Guest favorite
Home in Simpsonville
Charming 4 Bedroom classic home bourbon trail!
4 beds
May 18 – 23
ﺩ.ﺇ4,219 for 5 nights
for 5 nights
4.87 out of 5 average rating, 148 reviews
Guest favorite
Home in Simpsonville
The Haven Simpsonville* Bourbon Trail* 3 bed/3bath
Free cancellation
May 18 – 23
ﺩ.ﺇ4,757 for 5 nights
for 5 nights
5.0 out of 5 average rating, 7 reviews
Guest favorite
Home in Simpsonville
Comfortable sleek home bourbon trail
Free cancellation
Jun 9 – 14
ﺩ.ﺇ4,254 for 5 nights
for 5 nights
4.94 out of 5 average rating, 109 reviews
Guest favorite
Home in Simpsonville
Eastern Sky
3 beds
May 17 – 22
ﺩ.ﺇ3,207 for 5 nights
for 5 nights
4.86 out of 5 average rating, 7 reviews
Top guest favorite
Cottage in Simpsonville
Miles Around KY Cottage-Hot Tub
4 beds
May 17 – 22
ﺩ.ﺇ5,010 for 5 nights
for 5 nights
5.0 out of 5 average rating, 32 reviews
Top guest favorite
Room in Simpsonville
Stay with AmyCulinary teacher,
A Slice Of Bourbon Country 1 BR *Fresh Breakfast*
May 25 – 30
ﺩ.ﺇ1,899 for 5 nights
for 5 nights
5.0 out of 5 average rating, 49 reviews
Guest favorite
Home in Simpsonville
Derby Bourbon Trail Classic
Free cancellation
Jun 1 – 6
ﺩ.ﺇ4,628 for 5 nights
for 5 nights
4.9 out of 5 average rating, 31 reviews
Top guest favorite
Farm stay in Shelbyville
Cozy Retreat at Red Gate Farm
1 queen bed
May 16 – 21
ﺩ.ﺇ2,592 for 5 nights
for 5 nights
4.98 out of 5 average rating, 57 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, 20 reviews
Top guest favorite
Home in Simpsonville
Sleeps 24, 6BR, 4BA, Hot Tub
Free cancellation
Jun 8 – 13
ﺩ.ﺇ22,178 for 5 nights
for 5 nights
4.95 out of 5 average rating, 65 reviews
Guest favorite
Farm stay in Simpsonville
Spacious Home with Beautiful Views
4 beds
May 17 – 22
ﺩ.ﺇ3,812 for 5 nights
for 5 nights
4.89 out of 5 average rating, 66 reviews
Top guest favorite
Cabin in Louisville
Historic Cabin by Bourbon Trail
2 beds
May 17 – 22
ﺩ.ﺇ2,820 for 5 nights
for 5 nights
5.0 out of 5 average rating, 204 reviews
Guest favorite
Farm stay in Simpsonville
Farm House - near Bourbon Trail & Pet Friendly
Free cancellation
Jun 1 – 6
ﺩ.ﺇ3,659 for 5 nights
for 5 nights
4.87 out of 5 average rating, 70 reviews
Top guest favorite
Home in Finchville
Country Retreat on Bourbon Trail - Fire Pit - King
Free cancellation
Jun 9 – 14
ﺩ.ﺇ4,322 for 5 nights
for 5 nights
5.0 out of 5 average rating, 32 reviews
Top guest favorite
Farm stay in Simpsonville
4BR Farm~Bourbon Trail~private pool~horses
Free cancellation
Sep 29 – Oct 4
ﺩ.ﺇ10,224 for 5 nights
for 5 nights
5.0 out of 5 average rating, 25 reviews
Top guest favorite
Farm stay in Pleasureville
Nelson Farms Bunkhouse
5 beds
May 15 – 20
ﺩ.ﺇ2,841 for 5 nights
for 5 nights
5.0 out of 5 average rating, 10 reviews
Top guest favorite
Condo in Shelbyville
Your Kentucky Home Away From Home
2 beds
May 16 – 21
ﺩ.ﺇ2,559 for 5 nights
for 5 nights
4.88 out of 5 average rating, 127 reviews