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Search results; 662 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, 297 reviews
Guest favourite
Home in Charlestown
The Sunset House-Hot Tub-Sauna
5 bedrooms, 5 beds, 3 bathrooms
13–18 Sept
4.95 out of 5 average rating, 91 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
Top guest favourite
Home in Charlestown
The Cooper House in Charlestown, MD
4 bedrooms, 6 beds, 4 bathrooms
19–24 Sept
4.99 out of 5 average rating, 95 reviews
Top guest favourite
Home in North East
Waterfront Historical District Home Near River
3 bedrooms, 4 beds, 2 bathrooms
24–29 Sept
5.0 out of 5 average rating, 20 reviews
Superhost
Home in Charlestown
Stay Blue Heron, Coastal Comfort in Charlestown.
4 bedrooms, 5 beds, 3.5 bathrooms
13–18 Sept
4.58 out of 5 average rating, 12 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
Home in North East
Pool House by the North East River
3 bedrooms, 6 beds, 2.5 bathrooms
21–26 Sept
4.7 out of 5 average rating, 37 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
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
Cottage in Charlestown
Key West Cottage in Charlestown, MD
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
4.92 out of 5 average rating, 26 reviews
Top guest favourite
Flat in Havre de Grace
The Sappington House * easy stay near 95 * HdG
3 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.92 out of 5 average rating, 60 reviews
Top guest favourite
Home in North East
Riverfront Haven @ Hances Point
4 bedrooms, 7 beds, 3 bathrooms
8–13 Sept
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Home in Perryville
Chesapeake Waterfront Vacation Rental with Dock
5 bedrooms, 12 beds, 2 bathrooms
4–9 Oct
4.94 out of 5 average rating, 31 reviews
Home in Elkton
The C&D Retreat
3 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 4 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
Top guest favourite
Home in Elkton
Woodland Retreat at Fair Hill-Relax and Recharge
6 bedrooms, 7 beds, 4.5 bathrooms
5–10 Oct
4.92 out of 5 average rating, 39 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
Top guest favourite
Home in Perryville
Stunning Chesapeake Bay views, 5 bedrooms, 3 bath
5 bedrooms, 9 beds, 3 bathrooms
8–13 Sept
5.0 out of 5 average rating, 45 reviews