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Search results; Over 1,000 homes in Chesapeake Beach

Home in Chesapeake Beach
Bay Bliss - Beach Cottage
2 bedrooms, 5 beds, 1 private bathroom
1–6 Feb
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4.91 out of 5 average rating, 66 reviews
Top guest favourite
Home in North Beach
Bayfront Home with Amazing Rooftop Deck!
5 bedrooms, 10 beds, 4.5 bathrooms
13–18 Sept
4.98 out of 5 average rating, 133 reviews
Home in North Beach
Bay watch Oasis Awaits!
3 bedrooms, 1 king bed, 2.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 3 reviews
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
Top guest favourite
Guest suite in Lusby
Waterfront on St. Leonard Creek at Fort Hill
2 bedrooms, 4 beds, 2 bathrooms
27 Oct – 1 Nov
4.98 out of 5 average rating, 118 reviews
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, 250 reviews
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, 186 reviews
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, 60 reviews
Superhost
Home in Stevensville
Private & Peaceful | Water Views, Big Deck, Games
3 bedrooms, 5 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Huntingtown
Grand Tudor Home w/ Saltwater Pool & Hot Tub
5 bedrooms, 6 beds, 3.5 bathrooms
9–14 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Royal Oak
Waterfront Family Retreat - mins from St. Michaels
6 bedrooms, 9 beds, 4.5 bathrooms
22–27 Sept
5.0 out of 5 average rating, 5 reviews
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
Top guest favourite
Home in Deale
Charming Waterfront 3BR Cottage on Chesapeake Bay
3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 10 reviews
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
Top guest favourite
Home in Cambridge
• Peaceful Point • A relaxing waterfront retreat
3 bedrooms, 7 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 63 reviews
Top guest favourite
Guest house in Owings
Relaxing retreat on the river.
1 king bed, 1 bathroom
26–31 Jan
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Lusby
Private Beach, Dock, Hottub @ Solomons Bay A-Frame
4 bedrooms, 7 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Cottage in Deale
"Seas the Bay Cottage" in Deale with Kayaks
3 bedrooms, 6 beds, 3 bathrooms
28 Sept – 3 Oct
4.97 out of 5 average rating, 95 reviews
Top guest favourite
Home in Hollywood
Waterfront Home: Osprey Getaway
4 bedrooms, 6 beds, 3 bathrooms
27 Sept – 2 Oct
4.99 out of 5 average rating, 107 reviews