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Search results; Over 1,000 homes in Chesapeake Beach

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Guest favourite
Cottage in Chesapeake Beach
Bay View Cliffside Cottage w/ Private Dog Yard
Studio, 1 bed, 1 private bathroom
8–13 Sept
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4.93 out of 5 average rating, 74 reviews
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Home in North Beach
Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces
2 bedrooms, 2 queen beds, 2.5 bathrooms
25–30 Nov
5.0 out of 5 average rating, 186 reviews
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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
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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
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Home in North Beach
Huge 4 BR Beach House | Fire Pit | Fenced Yard
4 bedrooms, 4 beds, 3 bathrooms
18–23 Oct
4.97 out of 5 average rating, 195 reviews
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Top guest favourite
Home in North Beach
Stunning North Beach Getaway w/ Inground Pool
4 bedrooms, 7 beds, 2 bathrooms
10–15 Sept
5.0 out of 5 average rating, 35 reviews
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Top guest favourite
Cottage in North Beach
Waterfront Cottage Near Herrington and North Beach
2 bedrooms, 3 beds, 2 bathrooms
26–31 Oct
4.97 out of 5 average rating, 381 reviews
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Guest favourite
Home in North Beach
Emerald Bay
3 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Home in North Beach
Modern Bay Home a few blocks from Boardwalk
4 bedrooms, 5 beds, 4.5 bathrooms
25–30 Sept
5.0 out of 5 average rating, 21 reviews
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Top guest favourite
Home in North Beach
Comfy King Bed Home, walk to dinner & beach!
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 39 reviews
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Top guest favourite
Townhouse in North Beach
Beachside Oasis + Beach Passes | A Haven Away
3 bedrooms, 3 beds, 2 bathrooms
26 Sept – 1 Oct
4.96 out of 5 average rating, 249 reviews
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Top guest favourite
Home in North Beach
Sea La Vie
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
4.94 out of 5 average rating, 33 reviews
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Guest favourite
Home in North Beach
Cozy Cottage By The Beach-Pet Friendly
3 bedrooms, 4 beds, 2 bathrooms
12–17 Oct
4.94 out of 5 average rating, 48 reviews
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Cottage in North Beach
The Blue Crab Beach House - Free beach passes
2 bedrooms, 2 beds, 2 bathrooms
6–11 Sept
4.95 out of 5 average rating, 84 reviews
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Top guest favourite
Home in North Beach
The Licorne Beach Cottage
3 bedrooms, 3 beds, 2 bathrooms
3–8 Oct
5.0 out of 5 average rating, 19 reviews
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Top guest favourite
Home in North Beach
Waterfront- 5-Bedroom House
5 bedrooms, 12 beds, 5.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Home in Deale
Hannah’s Hideaway
3 bedrooms, 7 beds, 2 bathrooms
20–25 Oct
4.99 out of 5 average rating, 161 reviews
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Guest favourite
Home in Oak Grove
Private beach access, kayaks and fire pit!
3 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 10 reviews
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Top guest favourite
Home in West River
Cozy waterview home in West River!
3 bedrooms, 3 beds, 2.5 bathrooms
4–9 Oct
4.97 out of 5 average rating, 168 reviews