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Search results; Over 1,000 homes in Charlestown

Guest favourite
Cabin in Charlestown
Historic Shabby Cabin W/ Modern Comfort Sleeps 11!
3 bedrooms, 7 beds, 2.5 private bathrooms
11–16 Oct
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4.78 out of 5 average rating, 60 reviews
Guest favourite
Home in Charlestown
The Quaint Cottage -No cleaning fee. Snack basket.
3 bedrooms, 3 beds, 1 bathroom
18–23 Sept
5.0 out of 5 average rating, 18 reviews
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
Guest favourite
Guest house in Charlestown
Watson Mansion Carriage House
1 bedroom, 2 queen beds, 1.5 bathrooms
27 Sept – 2 Oct
4.81 out of 5 average rating, 48 reviews
Top guest favourite
Home in Clarksville
Derby Dreams City Convenience Meets Country Charm
4 bedrooms, 9 beds, 2.5 bathrooms
23–28 Oct
5.0 out of 5 average rating, 13 reviews
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
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, 33 reviews
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
Top guest favourite
Home in Jeffersonville
Southern Indiana Patio Home
3 bedrooms, 3 beds, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 71 reviews
Home in Charlestown
15 Mi to Louisville: Game Room + EV Charger
4 bedrooms, 4 beds, 3 bathrooms
28 Sept – 3 Oct
Guest favourite
Home in Jeffersonville
18 minutes to Churchill Downs! King, Queen & full!
3 bedrooms, 4 beds, 2.5 bathrooms
4–9 Oct
4.87 out of 5 average rating, 207 reviews
Guest favourite
Home in Louisville
St. Matthew’s - Walk to Shops & Restaurants
2 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
4.94 out of 5 average rating, 32 reviews
Guest favourite
Flat in Prospect
Exclusive Farmhouse w/ a Romantic Garden View!
1 bedroom, 2 single beds, 1 bathroom
29 Sept – 4 Oct
4.88 out of 5 average rating, 96 reviews
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
Top guest favourite
Rooms in Jeffersonville
Sleep Easy in Jeffersonville 1-2 bed sleep up to 4
2 bedrooms, 3 beds, 1.5 bathrooms
3–8 Oct
4.99 out of 5 average rating, 368 reviews
Guest favourite
Home in Prospect
LUX Waterside Retreat|Geo Dome+Outdoor Fire Table
3 bedrooms, 4 beds, 2.5 bathrooms
19–24 Oct
4.98 out of 5 average rating, 130 reviews
Top guest favourite
Guest suite in Prospect
Private Prospect Flat
2 bedrooms, 3 beds, 1 bathroom
28 Sept – 3 Oct
4.97 out of 5 average rating, 270 reviews
Top guest favourite
Home in Bedford
Atoka Farms
3 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
4.99 out of 5 average rating, 230 reviews
Top guest favourite
Home in Jeffersonville
Southern Indiana Patio Home
3 bedrooms, 3 beds, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 17 reviews