Search results; Over 1,000 homes in Charlestown

Top guest favourite
Cottage in Charlestown
Key West Cottage in Charlestown, MD
3 bedrooms, 4 beds, 2 private bathrooms
18–23 Jul
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4.92 out of 5 average rating, 25 reviews
Guest favourite
Home in Charlestown
Catching Sunsets on the Bay
3 bedrooms, 3 beds
17–22 Jul
4.99 out of 5 average rating, 75 reviews
Superhost
Home in Charlestown
Long Beach Wellness Retreat Hot tub/Sauna/Plunge
1 bedroom, 2 beds
31 Jul – 5 Aug
New place to stay
Top guest favourite
Cottage in Charlestown
Long Beach Cottage, Hot Tub, Beachfront
1 bedroom, 1 king bed
20–25 Sept
4.96 out of 5 average rating, 278 reviews
Superhost
Home in Charlestown
Stay Blue Heron, Coastal Comfort in Charlestown.
4 bedrooms, 5 beds
19–24 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Room in Charlestown
"Sunrise on the River"
2 beds
11–16 Jul
4.99 out of 5 average rating, 98 reviews
Guest favourite
Home in Charlestown
The Sunset House-Hot Tub-Sauna
5 bedrooms, 5 beds
16–21 Aug
4.95 out of 5 average rating, 82 reviews
Guest favourite
Cottage in Charlestown
Charlestown Cottage at Cattail Bend
2 bedrooms, 3 beds
11–16 Jul
4.85 out of 5 average rating, 109 reviews
Top guest favourite
Home in Charlestown
The Cooper House in Charlestown, MD
4 bedrooms, 6 beds
26–31 Jul
4.99 out of 5 average rating, 86 reviews
Guest favourite
Home in North East
Waterfront Historical District Home Near River
3 bedrooms, 4 beds
22–27 Jul
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Home in Perryville
Upper Chesapeake Getaway
3 bedrooms, 6 beds
30 Aug – 4 Sept
4.98 out of 5 average rating, 160 reviews
Top guest favourite
Home in North East
Boho River Cottage
2 bedrooms, 3 beds
25–30 Jul
4.98 out of 5 average rating, 80 reviews
Top guest favourite
Cottage in North East
Persimmon Pastures
3 bedrooms, 3 beds
14–19 Aug
4.98 out of 5 average rating, 687 reviews
Superhost
Home in Havre de Grace
Villa Girard charming river and bay getaway
3 bedrooms, 3 beds
5–10 Jul
New place to stay
Guest favourite
Room in Chesapeake City
Cafe on the Bay - breakfast included!
1 queen bed
12–17 Jul
4.95 out of 5 average rating, 207 reviews
Guest favourite
Cottage in Port Deposit
The River Cottage
1 bedroom, 3 beds
26–31 Jul
4.94 out of 5 average rating, 343 reviews
Top guest favourite
Guest suite in North East
Carriage House Suite on NE Creek!
1 bedroom, 1 queen bed
21–26 Jul
4.97 out of 5 average rating, 135 reviews
Home in Charlestown
Cozy cape cod in water oriented Community near I95
3 bedrooms, 3 beds
18–23 Aug
4.84 out of 5 average rating, 115 reviews
Top guest favourite
Room in Perryville
North River Hideaway | King Suite
1 king bed
2–7 Jul
5.0 out of 5 average rating, 16 reviews