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Search results; Over 1,000 homes in Chesapeake Beach

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Top guest favourite
Home in Chesapeake Beach
Mid-Century Modern: Direct Private Beach Access
2 bedrooms, 2 beds, 1 private bathroom
26–31 Oct
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4.98 out of 5 average rating, 55 reviews
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Top guest favourite
Home in North Beach
Bayfront Home with Amazing Rooftop Deck!
5 bedrooms, 10 beds, 4.5 bathrooms
25–30 Sept
4.98 out of 5 average rating, 133 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
10–15 Nov
4.97 out of 5 average rating, 381 reviews
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Top guest favourite
Home in North Beach
Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces
2 bedrooms, 2 queen beds, 2.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 189 reviews
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Home in North Beach
Sea La Vie
3 bedrooms, 3 beds, 2 bathrooms
5–10 Oct
4.94 out of 5 average rating, 34 reviews
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Guest favourite
Home in North Beach
Bay Beach House | Screened Porch TV | Walkable
4 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.86 out of 5 average rating, 7 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
20–25 Sept
5.0 out of 5 average rating, 40 reviews
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Guest favourite
Home in North Beach
Emerald Bay
3 bedrooms, 4 beds, 2 bathrooms
25–30 Sept
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Home in North Beach
Huge 4 BR Beach House | Fire Pit | Fenced Yard
4 bedrooms, 4 beds, 3 bathrooms
25–30 Oct
4.97 out of 5 average rating, 197 reviews
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Home in North Beach
Bay watch Oasis Awaits!
3 bedrooms, 1 king bed, 2.5 bathrooms
18–23 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Guest suite in North Beach
Charming 1BR Bungalow Guest Suite | Close To Water
1 bedroom, 1 queen bed, 1 bathroom
24–29 Sept
4.97 out of 5 average rating, 61 reviews
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Top guest favourite
Home in Shady Side
Canary Pointe-A popular getaway for 2!
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 286 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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Guest favourite
Home in North Beach
The Licorne Beach Cottage
3 bedrooms, 3 beds, 2 bathrooms
3–8 Oct
4.95 out of 5 average rating, 22 reviews
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Top guest favourite
Cottage in North Beach
The Blue Crab Beach House - Free beach passes
2 bedrooms, 2 beds, 2 bathrooms
25–30 Oct
4.95 out of 5 average rating, 85 reviews
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Home in North Beach
Waterfront- 5-Bedroom House
5 bedrooms, 12 beds, 5.5 bathrooms
23–28 Sept
5.0 out of 5 average rating, 7 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, 252 reviews
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Guest favourite
Hotel room in North Beach
Guest Quarters at the Inn - 102
1 bedroom, 2 queen beds, 1 bathroom
29 Sept – 4 Oct
5.0 out of 5 average rating, 32 reviews