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Search results; Over 1,000 homes in Chesapeake Beach

Top guest favourite
Home in North Beach
Huge 4 BR Beach House | Fire Pit | Fenced Yard
4 bedrooms, 4 beds, 3 bathrooms
20–25 Sept
4.97 out of 5 average rating, 194 reviews
Top guest favourite
Room in Deale
Sunrise Suite Exquisite Bay View Lux/Rom/Spiritual
1 bed, 1 bathroom
30 Sept – 5 Oct
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in North Beach
Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces
2 bedrooms, 2 queen beds, 2.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 185 reviews
Top guest favourite
Home in North Beach
Bayfront Home with Amazing Rooftop Deck!
5 bedrooms, 10 beds, 4.5 bathrooms
8–13 Sept
4.98 out of 5 average rating, 133 reviews
Top guest favourite
Guest house in Owings
Relaxing retreat on the river.
1 king bed, 1 bathroom
26–31 Jan
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Place to stay in Cambridge
Wye Three Oaks
2 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
4.96 out of 5 average rating, 104 reviews
Top guest favourite
Cottage in Leonardtown
Waterfront Cottage ❤️ Private Beach, Dock & Kayaks
3 bedrooms, 4 beds, 2.5 bathrooms
8–13 Sept
4.97 out of 5 average rating, 134 reviews
Top guest favourite
Room in Cambridge
Sailor's Retreat Captain's Quarters
1 king bed, 1 bathroom
1–6 Oct
4.98 out of 5 average rating, 96 reviews
Guest favourite
Home in North Beach
Bay Beach House | Screened Porch TV | Walkable
4 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.86 out of 5 average rating, 7 reviews
Top guest favourite
Guest house in St. Leonard
Studio on the Bay.
1 bedroom, 1 queen bed, 1 bathroom
9–14 Sept
4.97 out of 5 average rating, 124 reviews
Top guest favourite
Home in North Beach
Sea La Vie
3 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
4.94 out of 5 average rating, 32 reviews
Top guest favourite
Guest suite in North Beach
Charming 1BR Bungalow Guest Suite | Close To Water
1 bedroom, 1 queen bed, 1 bathroom
12–17 Oct
4.97 out of 5 average rating, 59 reviews
Top guest favourite
Home in Lusby
Cove Point Beach Home 1 &1/2 blocks to Beach
3 bedrooms, 4 beds, 1.5 bathrooms
27 Sept – 2 Oct
4.99 out of 5 average rating, 241 reviews
Home in Montross
Crystal Blue: Waterfront home on the Potomac River
3 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
New place to stay
Top guest favourite
Home in Solomons
The Little House on Back Creek
2 bedrooms, 2 beds, 2.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 139 reviews
Top guest favourite
Home in Hollywood
Waterfront Home: Osprey Getaway
4 bedrooms, 6 beds, 3 bathrooms
9–14 Sept
4.99 out of 5 average rating, 106 reviews
Top guest favourite
Home in Cambridge
Gorgeous, Waterfront Home Is Perfect for Families!
7 bedrooms, 12 beds, 5 bathrooms
13–18 Sept
4.96 out of 5 average rating, 139 reviews
Top guest favourite
Farm stay in Brandywine
Convenient Cozy Farm Cottage 15 Miles from DC
2 bedrooms, 3 beds, 1 bathroom
1–6 Sept
4.94 out of 5 average rating, 17 reviews