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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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Guest favourite
Home in Jeffersonville
BRAND NEW, Jeff, IN Cottage, The Newport
4 bedrooms, 5 beds, 2 bathrooms
29 Sept – 4 Oct
4.93 out of 5 average rating, 121 reviews
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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 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 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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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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Top guest favourite
Home in Jeffersonville
Cozy Neighborhood Home - 10 min to Louisville!
2 bedrooms, 2 queen beds, 2 bathrooms
6–11 Oct
4.95 out of 5 average rating, 114 reviews
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Top guest favourite
Home in Jeffersonville
Happy Home / Neat and cosy accommodation experience / With electric vehicle charging socket
3 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 34 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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Guest favourite
Home in Jeffersonville
Quiet Home w/ Sunroom & Fire Pit Near Downtown
3 bedrooms, 3 beds, 1 bathroom
11–16 Oct
4.96 out of 5 average rating, 115 reviews
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Top guest favourite
Farm stay in Goshen
The Coop
2 bedrooms, 2 double beds, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 382 reviews
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Top guest favourite
Home in Bedford
Atoka Farms
3 bedrooms, 4 beds, 2 bathrooms
5–10 Oct
4.99 out of 5 average rating, 231 reviews
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Top guest favourite
Home in Jeffersonville
Beautiful RiverHouse with Elevator and Water Views
4 bedrooms, 9 beds, 3.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 38 reviews
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Top guest favourite
Flat in Memphis
Basement apt. Country setting 2 bedrooms 1 bath
2 bedrooms, 4 beds, 1 bathroom
5–10 Oct
4.94 out of 5 average rating, 48 reviews
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Top guest favourite
Guest suite in Floyds Knobs
Walkout Basement Unit - Private Entrance
2 bedrooms, 2 beds, 1 bathroom
29 Sept – 4 Oct
4.96 out of 5 average rating, 137 reviews
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Top guest favourite
Home in Jeffersonville
Southern Indiana Patio Home
3 bedrooms, 3 beds, 2 bathrooms
26–31 Oct
5.0 out of 5 average rating, 72 reviews