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Search results; 744 homes in Charlestown

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Top guest favourite
Room in Charlestown
"Sunrise on the River"
1 bedroom, 2 beds, 1 private bathroom
5–10 Oct
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4.99 out of 5 average rating, 104 reviews
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Top guest favourite
Home in North East
Waterfront Historical District Home Near River
3 bedrooms, 4 beds
22–27 Oct
5.0 out of 5 average rating, 21 reviews
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Top guest favourite
Home in Charlestown
The Cooper House in Charlestown, MD
4 bedrooms, 6 beds
4–9 Oct
4.99 out of 5 average rating, 98 reviews
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Guest favourite
Home in Charlestown
The Sunset House-Hot Tub-Sauna
5 bedrooms, 5 beds
4–9 Oct
4.95 out of 5 average rating, 91 reviews
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Top guest favourite
Home in Charlestown
Catching Sunsets on the Bay
3 bedrooms, 3 beds
4–9 Oct
4.99 out of 5 average rating, 84 reviews
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Guest favourite
Cottage in Charlestown
Charlestown Cottage at Cattail Bend
2 bedrooms, 3 beds
13–18 Oct
4.86 out of 5 average rating, 114 reviews
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Superhost
Home in Charlestown
Stay Blue Heron, Coastal Comfort in Charlestown.
4 bedrooms, 5 beds
4–9 Oct
4.62 out of 5 average rating, 13 reviews
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Top guest favourite
Home in Perryville
Upper Chesapeake Getaway
3 bedrooms, 6 beds
12–17 Oct
4.96 out of 5 average rating, 171 reviews
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Guest favourite
Home in Charlestown
Long Beach Wellness Retreat Hot tub/Sauna/Plunge
1 bedroom, 2 beds
22–27 Oct
5.0 out of 5 average rating, 12 reviews
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Guest favourite
Cottage in Charlestown
Key West Cottage in Charlestown, MD
3 bedrooms, 4 beds
4–9 Oct
4.92 out of 5 average rating, 26 reviews
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Top guest favourite
Home in Perryville
Top of the Chesapeake - Private Waterfront Home
5 bedrooms, 8 beds
11–16 Oct
4.92 out of 5 average rating, 249 reviews
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Top guest favourite
Cottage in Charlestown
Long Beach Cottage, Hot Tub,Wood Burning Fireplace
1 bedroom, 1 king bed
29 Nov – 4 Dec
4.96 out of 5 average rating, 298 reviews
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Top guest favourite
Cottage in North East
Cottage Just Off North East's Main Street
1 bedroom, 1 queen bed
18–23 Oct
4.94 out of 5 average rating, 450 reviews
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Top guest favourite
Flat in Charlestown
The Osprey Nest at the Cooper House
2 bedrooms, 3 beds
3–8 Jan
4.93 out of 5 average rating, 56 reviews
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Top guest favourite
Flat in Havre de Grace
Harbor Sweet
2 bedrooms, 3 beds
4–9 Oct
5.0 out of 5 average rating, 74 reviews
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Top guest favourite
Home in North East
Boho River Cottage
2 bedrooms, 3 beds
4–9 Oct
4.98 out of 5 average rating, 89 reviews
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Top guest favourite
Home in North East
Riverfront Haven @ Hances Point
4 bedrooms, 7 beds
1–6 Oct
5.0 out of 5 average rating, 34 reviews
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Guest favourite
Home in North East
The Fishing Factory
3 bedrooms, 7 beds
11–16 Oct
4.95 out of 5 average rating, 109 reviews
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Guest favourite
Home in Elkton
Chesapeake Point | Waterfront w/ HOT TUB + Beach!
7 bedrooms, 10 beds
6–11 Oct
4.92 out of 5 average rating, 39 reviews