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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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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
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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Home in North Beach
Bay Beach House | Screened Porch TV | Walkable
4 bedrooms, 4 beds, 2 bathrooms
11–16 Oct
4.86 out of 5 average rating, 7 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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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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Flat in North Beach
Waterfront on the North Beach Boardwalk
2 bedrooms, 2 beds, 1.5 bathrooms
12–17 Oct
4.93 out of 5 average rating, 28 reviews
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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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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, 198 reviews
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Cottage in North Beach
The Blue Crab Beach House - Free beach passes
2 bedrooms, 2 beds, 2 bathrooms
1–6 Oct
4.95 out of 5 average rating, 85 reviews
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Home in Stevensville
Private & Peaceful Water Views, Big Deck, Games
3 bedrooms, 5 beds, 3 bathrooms
4–9 Oct
5.0 out of 5 average rating, 6 reviews
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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, 49 reviews
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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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Home in North Beach
Stunning North Beach Getaway w/ Inground Pool
4 bedrooms, 7 beds, 2 bathrooms
11–16 Oct
5.0 out of 5 average rating, 37 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
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Guest favourite
Home in Shady Side
Waterfront Coastal Retreat w/ Beach Access
3 bedrooms, 1 bathroom
17–22 Oct
5.0 out of 5 average rating, 15 reviews
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Home in North Beach
Waterfront- 5-Bedroom House
5 bedrooms, 12 beds, 5.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 7 reviews
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Home in Hague
Indoor Pool, Beach, Game & Movie Cottage Sleeps 21
8 bedrooms, 15 beds, 3 bathrooms
1–6 Oct
5.0 out of 5 average rating, 20 reviews
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Top guest favourite
Cottage in Leonardtown
Waterfront Cottage ❤️ Private Beach, Dock & Kayaks
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Oct
4.97 out of 5 average rating, 137 reviews