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Search results; 646 homes in Charlestown

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
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
20–25 Sept
4.95 out of 5 average rating, 91 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
Superhost
Flat in Perryville
Cottage House by the Bay
1 bedroom, 1 queen bed, 1 bathroom
21–26 Nov
New place to stay
Top guest favourite
Room in Charlestown
"Sunrise on the River"
2 beds, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 104 reviews
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, 96 reviews
Top guest favourite
Home in North East
Riverfront Haven @ Hances Point
4 bedrooms, 7 beds, 3 bathrooms
21–26 Sept
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Cottage in North East
Vintage Waterfront Cottage with Stunning Sunsets
2 bedrooms, 4 beds, 2.5 bathrooms
24–29 Sept
5.0 out of 5 average rating, 65 reviews
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, 11 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, 171 reviews
Guest favourite
Cabin in North East
Bayview Cottage
2 bedrooms, 2 queen beds, 1 bathroom
15–20 Sept
4.9 out of 5 average rating, 69 reviews
Superhost
Home in Charlestown
Stay Blue Heron, Coastal Comfort in Charlestown.
4 bedrooms, 5 beds, 3.5 bathrooms
23–28 Sept
4.62 out of 5 average rating, 13 reviews
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, 448 reviews
Guest favourite
Home in Perryville
Waldins Chesapeake
3 bedrooms, 4 beds, 1.5 bathrooms
4–9 Oct
4.9 out of 5 average rating, 10 reviews
Home in North East
Pool House by the North East River
3 bedrooms, 6 beds, 2.5 bathrooms
27 Sept – 2 Oct
4.7 out of 5 average rating, 37 reviews
Guest favourite
Home in Elkton
Chesapeake Point | Waterfront w/ HOT TUB + Beach!
7 bedrooms, 10 beds, 4.5 bathrooms
15–20 Sept
4.92 out of 5 average rating, 39 reviews
Superhost
Resort in North East
Beautiful King Bayside Room
1 bedroom, 3 beds, 1 bathroom
24–29 Sept
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