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Search results; Over 1,000 homes in Chesapeake Beach

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Top guest favourite
Cottage in North Beach
Waterfront Cottage Near Herrington and North Beach
2 bedrooms, 3 beds, 2 bathrooms
18–23 Nov
4.97 out of 5 average rating, 381 reviews
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Home in North Beach
Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces
2 bedrooms, 2 queen beds, 2.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 189 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
4–9 Oct
4.95 out of 5 average rating, 85 reviews
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Top guest favourite
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
Cozy Cottage By The Beach-Pet Friendly
3 bedrooms, 4 beds, 2 bathrooms
12–17 Oct
4.94 out of 5 average rating, 50 reviews
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Guest favourite
Home in North Beach
Bay Beach House | Screened Porch TV | Walkable
4 bedrooms, 4 beds, 2 bathrooms
11–16 Oct
4.88 out of 5 average rating, 8 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
1–6 Oct
5.0 out of 5 average rating, 40 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
12–17 Oct
5.0 out of 5 average rating, 21 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, 199 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
4–9 Oct
4.96 out of 5 average rating, 252 reviews
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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, 62 reviews
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Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds, 1 bathroom
3–8 Oct
4.97 out of 5 average rating, 473 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
25–30 Oct
4.98 out of 5 average rating, 287 reviews
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Home in Deale
Hannah’s Hideaway
3 bedrooms, 7 beds, 2 bathrooms
28 Oct – 2 Nov
4.99 out of 5 average rating, 161 reviews
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Guest favourite
Home in North Beach
The Licorne Beach Cottage
3 bedrooms, 3 beds, 2 bathrooms
3–8 Oct
4.91 out of 5 average rating, 23 reviews
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Guest favourite
Home in North Beach
Emerald Bay
3 bedrooms, 4 beds, 2 bathrooms
13–18 Oct
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Home in Solomons
The Little House on Back Creek
2 bedrooms, 2 beds, 2.5 bathrooms
11–16 Oct
5.0 out of 5 average rating, 143 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, 170 reviews