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Search results; 745 homes in Charlestown

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Top guest favourite
Flat in Charlestown
The Osprey Nest at the Cooper House
2 bedrooms, 3 beds, 2 private bathrooms
3–8 Jan
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4.93 out of 5 average rating, 56 reviews
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Top guest favourite
Home in North East
Waterfront Historical District Home Near River
3 bedrooms, 4 beds, 2 bathrooms
22–27 Oct
5.0 out of 5 average rating, 21 reviews
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Guest favourite
Home in Charlestown
The Cooper House in Charlestown, MD
4 bedrooms, 6 beds, 4 bathrooms
4–9 Oct
4.95 out of 5 average rating, 99 reviews
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Top guest favourite
Home in Charlestown
Catching Sunsets on the Bay
3 bedrooms, 3 beds, 2.5 bathrooms
4–9 Oct
4.99 out of 5 average rating, 84 reviews
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Guest favourite
Home in Charlestown
The Sunset House-Hot Tub-Sauna
5 bedrooms, 5 beds, 3 bathrooms
4–9 Oct
4.93 out of 5 average rating, 92 reviews
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Guest favourite
Cottage in Charlestown
Charlestown Cottage at Cattail Bend
2 bedrooms, 3 beds, 1 bathroom
13–18 Oct
4.86 out of 5 average rating, 115 reviews
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Superhost
Home in Charlestown
Stay Blue Heron, Coastal Comfort in Charlestown.
4 bedrooms, 5 beds, 3.5 bathrooms
4–9 Oct
4.62 out of 5 average rating, 13 reviews
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Top guest favourite
Room in Charlestown
"Sunrise on the River"
2 beds, 1 bathroom
5–10 Oct
4.99 out of 5 average rating, 105 reviews
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Guest favourite
Cottage in Charlestown
Key West Cottage in Charlestown, MD
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
4.92 out of 5 average rating, 26 reviews
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Guest favourite
Home in Charlestown
Long Beach Wellness Retreat Hot tub/Sauna/Plunge
1 bedroom, 2 beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 13 reviews
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Top guest favourite
Home in Perryville
Top of the Chesapeake - Private Waterfront Home
5 bedrooms, 8 beds, 2 bathrooms
11–16 Oct
4.92 out of 5 average rating, 250 reviews
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Top guest favourite
Home in Perryville
Upper Chesapeake Getaway
3 bedrooms, 6 beds, 1.5 bathrooms
18–23 Oct
4.96 out of 5 average rating, 171 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, 1 bathroom
18–23 Oct
4.94 out of 5 average rating, 451 reviews
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Top guest favourite
Cottage in Charlestown
Long Beach Cottage, Hot Tub,Wood Burning Fireplace
1 bedroom, 1 king bed, 1 bathroom
29 Nov – 4 Dec
4.96 out of 5 average rating, 300 reviews
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Top guest favourite
Home in North East
Riverfront Haven @ Hances Point
4 bedrooms, 7 beds, 3 bathrooms
1–6 Oct
5.0 out of 5 average rating, 34 reviews
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Top guest favourite
Flat in Havre de Grace
Harbor Sweet
2 bedrooms, 3 beds, 1 bathroom
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, 1 bathroom
4–9 Oct
4.98 out of 5 average rating, 90 reviews
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Superhost
Home in Elkton
Cozy Cottage Elkton North East 3bed 2 bath Patio
3 bedrooms, 6 beds, 2 bathrooms
8–13 Nov
4.82 out of 5 average rating, 404 reviews
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Guest favourite
Home in North East
The Fishing Factory
3 bedrooms, 7 beds, 2.5 bathrooms
11–16 Oct
4.95 out of 5 average rating, 109 reviews