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Search results; 671 homes in Charlestown

Top guest favourite
Home in Charlestown
Catching Sunsets on the Bay
3 bedrooms, 3 beds, 2.5 private bathrooms
20–25 Sept
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4.99 out of 5 average rating, 84 reviews
Guest favourite
Home in Charlestown
The Sunset House-Hot Tub-Sauna
5 bedrooms, 5 beds
20–25 Sept
4.95 out of 5 average rating, 91 reviews
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
Guest favourite
Cottage in Charlestown
Charlestown Cottage at Cattail Bend
2 bedrooms, 3 beds
19–24 Sept
4.86 out of 5 average rating, 113 reviews
Top guest favourite
Room in Charlestown
"Sunrise on the River"
2 beds
20–25 Sept
4.99 out of 5 average rating, 104 reviews
Superhost
Flat in Perryville
Cottage House by the Bay
1 bedroom, 1 queen bed
21–26 Nov
New place to stay
Top guest favourite
Home in North East
Riverfront Haven @ Hances Point
4 bedrooms, 7 beds
21–26 Sept
5.0 out of 5 average rating, 33 reviews
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, 96 reviews
Top guest favourite
Cottage in North East
Vintage Waterfront Cottage with Stunning Sunsets
2 bedrooms, 4 beds
16–21 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
22–27 Oct
5.0 out of 5 average rating, 11 reviews
Guest favourite
Cabin in North East
Bayview Cottage
2 bedrooms, 2 queen beds
15–20 Sept
4.9 out of 5 average rating, 69 reviews
Top guest favourite
Home in Perryville
Upper Chesapeake Getaway
3 bedrooms, 6 beds
20–25 Sept
4.96 out of 5 average rating, 171 reviews
Superhost
Home in Charlestown
Stay Blue Heron, Coastal Comfort in Charlestown.
4 bedrooms, 5 beds
23–28 Sept
4.62 out of 5 average rating, 13 reviews
Guest favourite
Home in Elkton
Chesapeake Point | Waterfront w/ HOT TUB + Beach!
7 bedrooms, 10 beds
15–20 Sept
4.92 out of 5 average rating, 39 reviews
Top guest favourite
Cottage in North East
Cottage Just Off North East's Main Street
1 bedroom, 1 queen bed
20–25 Sept
4.94 out of 5 average rating, 448 reviews
Rooms in Perryville
North River Hideaway | Sleeps 8
2 bedrooms, 5 beds
15–20 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Perryville
Waldins Chesapeake
3 bedrooms, 3 beds
4–9 Oct
4.9 out of 5 average rating, 10 reviews
Superhost
Resort in North East
Beautiful King Bayside Room
1 bedroom, 3 beds
24–29 Sept
Top guest favourite
Home in North East
Red Point Lighthouse
4 bedrooms, 7 beds
20–25 Sept
4.96 out of 5 average rating, 137 reviews