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Search results; Over 1,000 homes in Simpsonville

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Top guest favourite
Room in Simpsonville
A Slice Of Bourbon Country 1 BR *Fresh Breakfast*
1 bedroom, 1 bed, 1.5 private bathrooms
4–9 Oct
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5.0 out of 5 average rating, 102 reviews
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Place to stay in Simpsonville
Private Lower Level King Bed/Farm View
2 bedrooms, 2 beds, 1 bathroom
11–16 Oct
4.99 out of 5 average rating, 783 reviews
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Home in Simpsonville
Luxury Country Retreat w 7 Bedroom | Bourbon Trail
7 bedrooms, 7 beds, 3.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 8 reviews
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Room in Simpsonville
Sky Blue Ensuite has a King bed & balcony.
1 king bed, 1 bathroom
1–6 Sept
4.99 out of 5 average rating, 625 reviews
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Flat in Simpsonville
Ridgecrest Estate. Comfort and Convenience.
1 king bed, 1 bathroom
6–11 Sept
4.98 out of 5 average rating, 141 reviews
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Cottage in Simpsonville
KY Cottage near Bourbon, Expo & Horse Park|Hot Tub
3 bedrooms, 4 beds, 2 bathrooms
21–26 Oct
5.0 out of 5 average rating, 68 reviews
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Home in Simpsonville
The Haven Simpsonville* Bourbon Trail* 3 bed/3bath
3 bedrooms, 3 queen beds, 3 bathrooms
6–11 Sept
4.98 out of 5 average rating, 40 reviews
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Home in Simpsonville
Eastern Sky
3 bedrooms, 3 beds, 2 bathrooms
5–10 Oct
4.95 out of 5 average rating, 43 reviews
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Home in Simpsonville
Sleeps 26, Hot Tub & Sauna - Near Bourbon Trail
6 bedrooms, 14 beds, 4 bathrooms
5–11 Oct
5.0 out of 5 average rating, 15 reviews
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Farm stay in Simpsonville
4BR Farm~Bourbon Trail~private heated pool~horses
4 bedrooms, 4 beds, 3 bathrooms
8–13 Sept
5.0 out of 5 average rating, 57 reviews
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Loft in Shelbyville
The Stick at Pondview
3 bedrooms, 4 beds, 1 bathroom
18–23 Oct
5.0 out of 5 average rating, 18 reviews
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Loft in Shelbyville
Close to Buffalo Trace/Transpo available-Must See
5 bedrooms, 5 beds, 3 bathrooms
1–6 Sept
4.98 out of 5 average rating, 123 reviews
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Cabin in Shelbyville
The Rec Farm-Log Cabin, Private Lake & Arcade
3 bedrooms, 7 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 21 reviews
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Farm stay in Simpsonville
Restored 1919 Farmhouse on 100 Private Acres
4 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
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Loft in Shelbyville
The Lucky Penny Downtown Loft - Central Location!
1 bedroom, 2 beds, 1 bathroom
12–17 Sept
4.92 out of 5 average rating, 51 reviews
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Barn in Louisville
Luxury modern barn home on a Kentucky horse farm
3 bedrooms, 4 beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 21 reviews
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Home in Shelbyville
Long Ridge Farm
3 bedrooms, 4 beds, 2.5 bathrooms
7–12 Sept
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Home in Louisville
Unique Serenity - Entire Home On Private 3-Acres
4 bedrooms, 6 beds, 4 bathrooms
12–17 Oct
5.0 out of 5 average rating, 64 reviews
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Farm stay in Simpsonville
Farm House - near Bourbon Trail & Pet Friendly
4 bedrooms, 4 beds, 1 bathroom
12–17 Dec
4.89 out of 5 average rating, 101 reviews