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Search results; Over 1,000 homes in Chesapeake Beach

Guest favourite
Cottage in Chesapeake Beach
Bay View Cliffside Cottage w/ Private Dog Yard
Studio, 1 bed, 1 private bathroom
9–14 Aug
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4.93 out of 5 average rating, 72 reviews
Top guest favourite
Home in North Beach
Sea La Vie
3 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
4.93 out of 5 average rating, 29 reviews
Top guest favourite
Home in North Beach
Modern Bay Home a few blocks from Boardwalk
4 bedrooms, 5 beds, 4.5 bathrooms
28 Aug – 2 Sept
5.0 out of 5 average rating, 16 reviews
Home in North Beach
Emerald Bay
3 bedrooms, 4 beds, 2 bathrooms
12–17 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Shady Side
A Happy Place
3 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 29 reviews
Top guest favourite
Home in North Beach
Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces
2 bedrooms, 2 queen beds, 2.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 184 reviews
Guest favourite
Home in North Beach
The Licorne Beach Cottage
3 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 17 reviews
Superhost
Home in West River
Cozy Bayside Retreat
2 bedrooms, 4 beds, 1.5 bathrooms
10–15 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Townhouse in North Beach
Beachside Oasis + Beach Passes | A Haven Away
3 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
4.96 out of 5 average rating, 245 reviews
Top guest favourite
Home in Church Creek
Blackwater Sika & Wildlife Retreat
3 bedrooms, 4 beds, 2 bathrooms
10–15 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Cottage in North Beach
The Blue Crab Beach House - Free beach passes
2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug
4.96 out of 5 average rating, 83 reviews
Top guest favourite
Cottage in Deale
"Seas the Bay Cottage" in Deale with Kayaks
3 bedrooms, 6 beds, 3 bathrooms
10–15 Aug
4.97 out of 5 average rating, 92 reviews
Top guest favourite
Home in North Beach
Huge 4 BR Beach House | Fire Pit | Fenced Yard
4 bedrooms, 4 beds, 3 bathrooms
17–22 Aug
4.97 out of 5 average rating, 194 reviews
Top guest favourite
Home in West River
Cozy waterview home in West River!
3 bedrooms, 3 beds, 2.5 bathrooms
16–21 Aug
4.97 out of 5 average rating, 164 reviews
Home in North Beach
Bay watch Oasis Awaits!
3 bedrooms, 1 king bed, 2.5 bathrooms
7–12 Aug
Top guest favourite
Home in Leonardtown
Water's Edge Cottage | Luxury Retreat
2 bedrooms, 2 beds, 2 bathrooms
13–18 Oct
4.99 out of 5 average rating, 137 reviews
Home in Silver Spring
NEW DC-Area Lux Stay with Jacuzzi/Sauna & Gameroom
4 bedrooms, 5 beds, 2.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Shady Side
Canary Pointe-A popular getaway for 2!
1 bedroom, 2 beds, 1 bathroom
21–26 Aug
4.99 out of 5 average rating, 273 reviews
Home in Huntingtown
Plum Point Cottage #3
2 bedrooms, 2 beds, 1 bathroom
10–15 Aug