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Search results; 665 homes in Charlestown

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Top guest favourite
Cottage in Charlestown
Long Beach Cottage, Hot Tub,Wood Burning Fireplace
1 bedroom, 1 bed, 1 private bathroom
29 Nov – 4 Dec
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4.96 out of 5 average rating, 298 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 Sunset House-Hot Tub-Sauna
5 bedrooms, 5 beds, 3 bathrooms
4–9 Oct
4.95 out of 5 average rating, 91 reviews
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Top guest favourite
Home in Charlestown
The Cooper House in Charlestown, MD
4 bedrooms, 6 beds, 4 bathrooms
4–9 Oct
4.99 out of 5 average rating, 98 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
Cottage in Charlestown
Charlestown Cottage at Cattail Bend
2 bedrooms, 3 beds, 1 bathroom
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, 3.5 bathrooms
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, 1.5 bathrooms
12–17 Oct
4.96 out of 5 average rating, 171 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, 104 reviews
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Guest favourite
Home in Charlestown
Long Beach Wellness Retreat Hot tub/Sauna/Plunge
1 bedroom, 2 beds, 1 bathroom
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, 2 bathrooms
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, 2 bathrooms
11–16 Oct
4.92 out of 5 average rating, 249 reviews
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Superhost
Home in Elkton
Cozy Cottage Elkton North East 3bed 2 bath Patio
3 bedrooms, 6 beds, 2 bathrooms
24–29 Oct
4.82 out of 5 average rating, 404 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, 33 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
Flat in Havre de Grace
The Sappington House - Eagle View
2 bedrooms, 3 beds, 1 bathroom
11–16 Oct
5.0 out of 5 average rating, 38 reviews
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Rooms in Perryville
North River Hideaway | Sleeps 8
2 bedrooms, 5 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Flat in Elkton
Cozy Nest Apartment- Close to the Chesapeake Bay
2 bedrooms, 4 beds, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 15 reviews
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Top guest favourite
Cottage in North East
Vintage Waterfront Cottage with Stunning Sunsets
2 bedrooms, 4 beds, 2.5 bathrooms
19–24 Oct
5.0 out of 5 average rating, 66 reviews