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Search results; Over 1,000 homes in Simpsonville

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Top guest favourite
Cottage in Simpsonville
KY Cottage near Bourbon, Expo & Horse Park|Hot Tub
3 bedrooms, 4 beds, 2 shared bathrooms
15–20 Nov
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5.0 out of 5 average rating, 71 reviews
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Top guest favourite
Place to stay in Simpsonville
Private Lower Level King Bed/Farm View
2 bedrooms, 2 beds
20–25 Oct
4.98 out of 5 average rating, 790 reviews
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Home in Simpsonville
Golf, Bourbon & Horses | The Kentucky Trifecta
4 bedrooms, 4 beds
11–16 Oct
New place to stay
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Guest favourite
Home in Simpsonville
Luxury Country Retreat w 7 Bedroom | Bourbon Trail
7 bedrooms, 7 beds
1–6 Oct
5.0 out of 5 average rating, 10 reviews
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Home in Simpsonville
Spacious Bourbon retreat near Downtown Louisville!
5 bedrooms, 6 beds
12–17 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Rooms in Simpsonville
Slice Of Bourbon Country 2 BR FreshBreakfast
2 bedrooms, 2 beds
30 Oct – 4 Nov
5.0 out of 5 average rating, 55 reviews
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Guest favourite
Home in Simpsonville
The Haven Simpsonville* Bourbon Trail* 3 bed/3bath
3 bedrooms, 3 queen beds
11–16 Oct
4.98 out of 5 average rating, 41 reviews
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Top guest favourite
Home in Simpsonville
Sleeps 26, Hot Tub & Sauna - Near Bourbon Trail
6 bedrooms, 14 beds
5–10 Oct
5.0 out of 5 average rating, 16 reviews
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Top guest favourite
Room in Simpsonville
Nautical, King bed w/sitting area.
1 king bed
1–6 Oct
4.99 out of 5 average rating, 249 reviews
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Top guest favourite
Home in Simpsonville
Eastern Sky
3 bedrooms, 3 beds
1–6 Nov
4.96 out of 5 average rating, 45 reviews
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Top guest favourite
Farm stay in Simpsonville
4BR Farm~Bourbon Trail~private heated pool~horses
4 bedrooms, 4 beds
10–15 Oct
5.0 out of 5 average rating, 57 reviews
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Farm stay in Simpsonville
Restored 1919 Farmhouse on 100 Private Acres
4 bedrooms, 3 beds
1–6 Oct
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Top guest favourite
Flat in Simpsonville
Ridgecrest Estate. Comfort and Convenience.
1 king bed
9–14 Oct
4.98 out of 5 average rating, 143 reviews
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Top guest favourite
Farm stay in Simpsonville
Farm House - near Bourbon Trail & Pet Friendly
4 bedrooms, 4 beds
12–17 Dec
4.89 out of 5 average rating, 102 reviews
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Top guest favourite
Home in Louisville
Entire House in Middletown - Trailers/RVs access
3 bedrooms, 3 queen beds
12–17 Oct
4.96 out of 5 average rating, 54 reviews
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Guest favourite
Home in Shelbyville
Hitching Post on the Bourbon Trl
5 bedrooms, 6 beds
12–17 Oct
5.0 out of 5 average rating, 13 reviews
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Top guest favourite
Home in Louisville
Unique Serenity - Entire Home On Private 3-Acres
4 bedrooms, 6 beds
24–29 Oct
5.0 out of 5 average rating, 64 reviews
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Guest suite in Simpsonville
Simply Simpsonville
1 bedroom, 1 queen bed
1–6 Oct
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Superhost
Home in Shelbyville
Cozy Kentucky Winter, Bourbon Trail, Location!
2 bedrooms, 5 beds
12–17 Oct
4.9 out of 5 average rating, 94 reviews