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Search results; 730 homes in Charlestown

Top guest favourite
Serviced apartment in Charlestown
The Osprey Nest at the Cooper House
2 bedrooms, 3 beds, 2 private bathrooms
3–8 Jan
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4.93 out of 5 average rating, 56 reviews
Guest favourite
Home in Charlestown
Catching Sunsets on the Bay
3 bedrooms, 3 beds, 2.5 bathrooms
17–22 Jul
4.99 out of 5 average rating, 76 reviews
Top guest favourite
Home in Charlestown
The Cooper House in Charlestown, MD
4 bedrooms, 6 beds, 4 bathrooms
26–31 Jul
4.99 out of 5 average rating, 87 reviews
Guest favourite
Home in Charlestown
The Sunset House-Hot Tub-Sauna
5 bedrooms, 5 beds, 3 bathrooms
5–10 Aug
4.95 out of 5 average rating, 83 reviews
Superhost
Home in Charlestown
Stay Blue Heron, Coastal Comfort in Charlestown.
4 bedrooms, 5 beds, 3.5 bathrooms
19–24 Jul
4.2 out of 5 average rating, 5 reviews
Guest favourite
Home in North East
Waterfront Historical District Home Near River
3 bedrooms, 4 beds, 2 bathrooms
5–10 Aug
5.0 out of 5 average rating, 15 reviews
Guest favourite
Cottage in Charlestown
Charlestown Cottage at Cattail Bend
2 bedrooms, 3 beds, 1 bathroom
11–16 Jul
4.85 out of 5 average rating, 109 reviews
Top guest favourite
Home in Perryville
Upper Chesapeake Getaway
3 bedrooms, 6 beds, 1.5 bathrooms
30 Aug – 4 Sept
4.98 out of 5 average rating, 161 reviews
Home in Charlestown
Cozy cape cod in water oriented Community near I95
3 bedrooms, 3 beds, 1 bathroom
18–23 Aug
4.84 out of 5 average rating, 115 reviews
Top guest favourite
Home in North East
Boho River Cottage
2 bedrooms, 3 beds, 1 bathroom
25–30 Jul
4.98 out of 5 average rating, 80 reviews
Top guest favourite
Cottage in Charlestown
Long Beach Cottage, Hot Tub, Beachfront
1 bedroom, 1 king bed, 1 bathroom
20–25 Sept
4.96 out of 5 average rating, 279 reviews
Top guest favourite
Room in Charlestown
"Sunrise on the River"
2 beds, 1 bathroom
11–16 Jul
4.99 out of 5 average rating, 98 reviews
Top guest favourite
Home in North East
Riverfront Haven @ Hances Point
4 bedrooms, 7 beds, 3 bathrooms
7–12 Jul
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Cottage in Charlestown
Key West Cottage in Charlestown, MD
3 bedrooms, 4 beds, 2 bathrooms
18–23 Jul
4.92 out of 5 average rating, 25 reviews
Top guest favourite
Cottage in North East
Persimmon Pastures
3 bedrooms, 3 beds, 1 bathroom
16–21 Aug
4.98 out of 5 average rating, 689 reviews
Guest favourite
Home in Perryville
Top of the Chesapeake - Private Waterfront Home
5 bedrooms, 8 beds, 2 bathrooms
31 Aug – 5 Sept
4.92 out of 5 average rating, 245 reviews
Top guest favourite
Home in Perryville
Chesapeake Waterfront Vacation Rental with Dock
5 bedrooms, 7 beds, 2 bathrooms
11–16 Jul
4.92 out of 5 average rating, 25 reviews
Top guest favourite
Flat in Havre de Grace
The Sappington House - Eagle View
2 bedrooms, 3 beds, 1 bathroom
26–31 Jul
5.0 out of 5 average rating, 20 reviews
Home in North East
Pool House by the North East River
3 bedrooms, 6 beds, 2.5 bathrooms
26–31 Jul
4.67 out of 5 average rating, 33 reviews