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Search results; Over 1,000 homes in Chesapeake Beach

Top guest favourite
Home in North Beach
Bayfront Home with Amazing Rooftop Deck!
5 bedrooms, 10 beds
21–26 Sept
4.98 out of 5 average rating, 133 reviews
Top guest favourite
Home in North Beach
Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces
2 bedrooms, 2 queen beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 188 reviews
Guest favourite
Home in North Beach
Bay Beach House | Screened Porch TV | Walkable
4 bedrooms, 4 beds
20–25 Sept
4.86 out of 5 average rating, 7 reviews
Top guest favourite
Cottage in North Beach
Waterfront Cottage Near Herrington and North Beach
2 bedrooms, 3 beds
10–15 Nov
4.97 out of 5 average rating, 381 reviews
Top guest favourite
Home in North Beach
Huge 4 BR Beach House | Fire Pit | Fenced Yard
4 bedrooms, 4 beds
18–23 Oct
4.97 out of 5 average rating, 196 reviews
Top guest favourite
Home in North Beach
Modern Bay Home a few blocks from Boardwalk
4 bedrooms, 5 beds
25–30 Sept
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in North Beach
Sea La Vie
3 bedrooms, 3 beds
15–20 Nov
4.94 out of 5 average rating, 34 reviews
Top guest favourite
Townhouse in North Beach
Beachside Oasis + Beach Passes | A Haven Away
3 bedrooms, 3 beds
26 Sept – 1 Oct
4.96 out of 5 average rating, 251 reviews
Top guest favourite
Home in Stevensville
Private & Peaceful Water Views, Big Deck, Games
3 bedrooms, 5 beds
21–26 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in North Beach
Stunning North Beach Getaway w/ Inground Pool
4 bedrooms, 7 beds
15–20 Sept
5.0 out of 5 average rating, 37 reviews
Top guest favourite
Home in North Beach
Emerald Bay
3 bedrooms, 4 beds
16–21 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in North Beach
Waterfront- 5-Bedroom House
5 bedrooms, 12 beds
23–28 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in North Beach
The Licorne Beach Cottage
3 bedrooms, 3 beds
3–8 Oct
4.95 out of 5 average rating, 22 reviews
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
4 bedrooms, 6 beds
4–9 Oct
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Home in North Beach
Comfy King Bed Home, walk to dinner & beach!
2 bedrooms, 2 beds
20–25 Sept
5.0 out of 5 average rating, 40 reviews
Guest favourite
Home in Prince Frederick
Chesapeake Escape Southern Md. Bay Adventures!
3 bedrooms, 7 beds
2–7 Oct
4.95 out of 5 average rating, 55 reviews
Top guest favourite
Home in Deale
Hannah’s Hideaway
3 bedrooms, 7 beds
20–25 Oct
4.99 out of 5 average rating, 161 reviews
Top guest favourite
Cottage in North Beach
The Blue Crab Beach House - Free beach passes
2 bedrooms, 2 beds
25–30 Oct
4.95 out of 5 average rating, 85 reviews