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Search results; 675 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
13–18 Sept
4.95 out of 5 average rating, 91 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, 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
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
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
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
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
Top guest favourite
Flat in Elkton
Cozy Nest Apartment- Close to the Chesapeake Bay
2 bedrooms, 4 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 15 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
17–22 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, 61 reviews
Superhost
Home in Elkton
Cozy Cottage Elkton North East 3bed 2 bath Patio
3 bedrooms, 6 beds, 2 bathrooms
24–29 Oct
4.83 out of 5 average rating, 403 reviews
Top guest favourite
Room in Charlestown
"Sunrise on the River"
2 beds, 1 bathroom
14–19 Sept
4.99 out of 5 average rating, 104 reviews
Top guest favourite
Flat in Havre de Grace
The Sappington House - Eagle View
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 38 reviews
Top guest favourite
Flat in Havre de Grace
Harbor Sweet
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 72 reviews
Top guest favourite
Home in North East
Boho River Cottage
2 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.98 out of 5 average rating, 88 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