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Search results; Over 1,000 homes in Charlestown

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Guest favourite
Flat in Charlestown
Cozy Hideaway
Studio, 3 beds, 1 private bathroom
29 Sept – 4 Oct
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4.93 out of 5 average rating, 73 reviews
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Guest favourite
Home in Charlestown
The Quaint Cottage -No cleaning fee. Snack basket.
3 bedrooms, 3 beds, 1 bathroom
3–8 Oct
5.0 out of 5 average rating, 19 reviews
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Guest favourite
Guest house in Charlestown
Watson Mansion Carriage House
1 bedroom, 2 queen beds, 1.5 bathrooms
27 Sept – 2 Oct
4.82 out of 5 average rating, 49 reviews
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Top guest favourite
Home in Charlestown
Patio Home Charlestown State Park & River Ridge
3 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 23 reviews
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Home in Jeffersonville
Dreamy Retreat | 10 Min to Louisville | Sleeps 7
4 bedrooms, 6 beds, 2 bathrooms
4–9 Oct
New place to stay
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Top guest favourite
Home in Prospect
Riverfront Cottage | Dock + Kayaks Near Louisville
2 bedrooms, 3 beds, 1 bathroom
12–17 Oct
5.0 out of 5 average rating, 36 reviews
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Home in Charlestown
15 Mi to Louisville: Game Room + EV Charger
4 bedrooms, 4 beds, 3 bathrooms
28 Sept – 3 Oct
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Top guest favourite
Home in Clarksville
Derby Dreams City Convenience Meets Country Charm
4 bedrooms, 9 beds, 2.5 bathrooms
24–29 Oct
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Home in Sellersburg
Comfort de Casa
3 bedrooms, 4 beds, 2 bathrooms
24–29 Dec
4.9 out of 5 average rating, 51 reviews
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Top guest favourite
Flat in Westport
The Back Porch Nook at Knock On Wood
1 bedroom, 2 beds, 1 bathroom
5–10 Oct
5.0 out of 5 average rating, 32 reviews
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Top guest favourite
Cabin in Henryville
Close to Louisville~Hot Tub~Fire Pit~Game Room
4 bedrooms, 6 beds, 3 bathrooms
15–20 Nov
4.97 out of 5 average rating, 385 reviews
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Guest favourite
Room in River Bluff
Shallow Creek Suite
1 bed, 1 bathroom
28 Sept – 3 Oct
4.8 out of 5 average rating, 50 reviews
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Top guest favourite
Barn in Sellersburg
WKU Man Cave (Efficiency Apartment)
1 bedroom, 1 queen bed, 1 bathroom
21–26 Sept
4.99 out of 5 average rating, 111 reviews
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Top guest favourite
Home in Floyds Knobs
Home with Breathtaking View
2 bedrooms, 2 beds, 2 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 115 reviews
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Guest favourite
Home in Jeffersonville
18 minutes to Churchill Downs! King, Queen & full!
3 bedrooms, 4 beds, 2.5 bathrooms
4–9 Oct
4.88 out of 5 average rating, 209 reviews
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Guest favourite
Flat in Clarksville
Beach Vibes 2 mile to Whiskey Row Bourbon City
1 bedroom, 2 beds, 1 bathroom
17–22 Oct
4.84 out of 5 average rating, 134 reviews
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Top guest favourite
Home in Goshen
The Boathouse: A Peaceful Paradise
2 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
4.91 out of 5 average rating, 33 reviews
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Top guest favourite
Home in Jeffersonville
Fossils on the River
3 bedrooms, 3 beds, 2 bathrooms
9–14 Dec
5.0 out of 5 average rating, 12 reviews
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Top guest favourite
Home in Jeffersonville
Beachfront River Cottage
1 bedroom, 1 bed, 1 bathroom
28 Sept – 3 Oct
4.95 out of 5 average rating, 106 reviews