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Search results; 664 homes in Charlestown

Top guest favourite
Cottage in Charlestown
Long Beach Cottage, Hot Tub,Wood Burning Fireplace
1 bedroom, 1 bed, 1 private bathroom
23–28 Nov
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4.96 out of 5 average rating, 296 reviews
Top guest favourite
Home in Charlestown
Catching Sunsets on the Bay
3 bedrooms, 3 beds, 2.5 bathrooms
20–25 Sept
4.99 out of 5 average rating, 84 reviews
Guest favourite
Home in Charlestown
The Sunset House-Hot Tub-Sauna
5 bedrooms, 5 beds, 3 bathrooms
13–18 Sept
4.94 out of 5 average rating, 90 reviews
Top guest favourite
Home in North East
Riverfront Haven @ Hances Point
4 bedrooms, 7 beds, 3 bathrooms
4–9 Sept
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Room in Charlestown
"Sunrise on the River"
2 beds, 1 bathroom
7–12 Sept
4.99 out of 5 average rating, 104 reviews
Guest favourite
Cottage in Charlestown
Charlestown Cottage at Cattail Bend
2 bedrooms, 3 beds, 1 bathroom
19–24 Sept
4.86 out of 5 average rating, 113 reviews
Top guest favourite
Home in North East
Downtown Living in North East, MD!
2 bedrooms, 3 beds, 1.5 bathrooms
13–18 Sept
4.99 out of 5 average rating, 195 reviews
Top guest favourite
Home in Charlestown
The Cooper House in Charlestown, MD
4 bedrooms, 6 beds, 4 bathrooms
7–12 Sept
4.99 out of 5 average rating, 95 reviews
Guest favourite
Home in Charlestown
Long Beach Wellness Retreat Hot tub/Sauna/Plunge
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Perryville
Waldins Chesapeake
3 bedrooms, 3 beds, 1.5 bathrooms
4–9 Oct
4.9 out of 5 average rating, 10 reviews
Top guest favourite
Home in Perryville
Upper Chesapeake Getaway
3 bedrooms, 6 beds, 1.5 bathrooms
20–25 Sept
4.96 out of 5 average rating, 170 reviews
Top guest favourite
Home in Perryville
Stunning Chesapeake Bay views, 5 bedrooms, 3 bath
5 bedrooms, 9 beds, 3 bathrooms
7–12 Sept
5.0 out of 5 average rating, 45 reviews
Top guest favourite
Home in Perryville
Top of the Chesapeake - Private Waterfront Home
5 bedrooms, 8 beds, 2 bathrooms
20–25 Sept
4.92 out of 5 average rating, 248 reviews
Guest favourite
Home in North East
Historic Creekside Home - 2br 2.5ba Downtown
2 bedrooms, 3 beds, 2.5 bathrooms
6–11 Sept
4.94 out of 5 average rating, 141 reviews
Superhost
Home in Charlestown
Stay Blue Heron, Coastal Comfort in Charlestown.
4 bedrooms, 5 beds, 3.5 bathrooms
13–18 Sept
4.55 out of 5 average rating, 11 reviews
Guest favourite
Home in North East
Spacious North East Home w/ Fenced Yard & Fire Pit
5 bedrooms, 6 beds, 3 bathrooms
25–30 Oct
5.0 out of 5 average rating, 31 reviews
Superhost
Resort in North East
Beautiful King Bayside Room
1 bedroom, 3 beds, 1 bathroom
13–18 Sept
Top guest favourite
Cottage in North East
Cottage Just Off North East's Main Street
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.94 out of 5 average rating, 445 reviews
Top guest favourite
Home in North East
Red Point Lighthouse
4 bedrooms, 7 beds, 4 bathrooms
20–25 Sept
4.96 out of 5 average rating, 137 reviews