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Search results; 596 homes in Chaplin

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Guest favourite
Farm stay in Chaplin
Cottage Retreat at Tiwazzen Farm
1 bedroom, 1 bed, 1 private bathroom
16–21 Oct
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4.95 out of 5 average rating, 123 reviews
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Top guest favourite
Home in Bloomfield
Relaxing Bourbon Trail Countryside Home & GameRoom
3 bedrooms, 4 beds, 3 bathrooms
18–23 Oct
4.97 out of 5 average rating, 39 reviews
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Top guest favourite
Home in Bloomfield
Charred Oak Reserve-Sleeps 10 Hot Tub, Firepit
5 bedrooms, 5 beds, 3 bathrooms
25–30 Oct
5.0 out of 5 average rating, 29 reviews
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Guest favourite
Home in Bloomfield
Hilltop Retreat-Bourbon Trail-Pool w/Slide-Hot Tub
5 bedrooms, 6 beds, 4 bathrooms
12–17 Oct
4.89 out of 5 average rating, 18 reviews
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Top guest favourite
Home in Bloomfield
Miss Allie's Homestead
4 bedrooms, 4 beds, 3 bathrooms
1–6 Oct
4.95 out of 5 average rating, 59 reviews
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Guest favourite
Cabin in Willisburg
Bourbon Trail Cabin - Central to the Distilleries
4 bedrooms, 6 beds, 2.5 bathrooms
26–31 Oct
4.9 out of 5 average rating, 138 reviews
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Cabin in Willisburg
The Arthur Farnsworth Cottage
2 bedrooms, 3 beds, 1 bathroom
1–6 Oct
New place to stay
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Top guest favourite
Home in Chaplin
Bourbon Trail Estate | 6BR | Pickleball | Hot Tub
6 bedrooms, 6 beds, 4.5 bathrooms
18–23 Oct
4.93 out of 5 average rating, 15 reviews
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Top guest favourite
Shipping container in Chaplin
Container home on Bourbon Trail 3 beds
3 bedrooms, 3 beds, 1 bathroom
29 Nov – 4 Dec
5.0 out of 5 average rating, 20 reviews
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Guest favourite
Cabin in Bloomfield
Boone's Cabin
4 bedrooms, 4 beds, 2 bathrooms
1–6 Oct
4.98 out of 5 average rating, 54 reviews
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Guest favourite
Home in Bloomfield
The Clayborn House
3 bedrooms, 3 queen beds, 2 bathrooms
1–6 Oct
4.93 out of 5 average rating, 27 reviews
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Guest favourite
Cabin in Willisburg
Bourbon Trail Cabin | Hot Tub Fire Pit | Sleeps 6
3 bedrooms, 4 beds, 1 bathroom
16–21 Oct
4.88 out of 5 average rating, 8 reviews
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Tiny home in Willisburg
Perfect Getaway
3 bedrooms, 5 beds, 1 bathroom
1–6 Oct
New place to stay
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Guest favourite
Holiday home in Bloomfield
The Cosmopolitan
1 bedroom, 1 bed, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 7 reviews
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Guest favourite
Cabin in Bloomfield
Family Holiday Cabin in Kentucky w/ Hot Tub!
3 bedrooms, 6 beds, 2 bathrooms
25–30 Oct
5.0 out of 5 average rating, 10 reviews
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Cottage in Taylorsville
Lake Refuge near Louisville & Bourbon Trail #52
3 bedrooms, 7 beds, 3 bathrooms
4–9 Oct
4.87 out of 5 average rating, 157 reviews
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Home in Taylorsville
Peaceful 56-Acre Farm Retreat Near Louisville
2 bedrooms, 2 beds, 2 bathrooms
1–6 Oct
New place to stay
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Top guest favourite
Home in Springfield
Scenic Getaway near Bardstown & Bourbon Trail
3 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 29 reviews
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Cabin in Bloomfield
The Baker’s Acres Luxurious 2100 sq ft on 61 Acres
3 bedrooms, 3 bathrooms
5–10 Oct