A harbor with boats docked, a pier, and a row of houses along the water.

Chesapeake Beach cottages

We found 52 cottages — enter your dates for availability

Explore Chesapeake Beach cottage rentals

Image of 3 bedroom, waterfront cottage on the shores of the Chesapeake Bay.

3 bedroom, waterfront cottage on the shores of the Chesapeake Bay.

Sleeps 8 · 3 bedrooms · 2 bathrooms

Image of Cliffside Chesapeake Bay Cottage: Pet-friendly, Easy DC Drive

Cliffside Chesapeake Bay Cottage: Pet-friendly, Easy DC Drive

Sleeps 2 · 1 bedroom · 1 bathroom

Image of Updated North Beach Cottage: Pet Friendly!

Premier Host

Updated North Beach Cottage: Pet Friendly!

Sleeps 8 · 3 bedrooms · 2 bathrooms

Image of Cottage Located on the Patuxent River!

Premier Host

Cottage Located on the Patuxent River!

Sleeps 2 · 1 bedroom · 1 bathroom

Image of Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Premier Host

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Sleeps 8 · 3 bedrooms · 2+ bathrooms

Image of Soul Oasis - home on the Chesapeake Bay

Premier Host

Soul Oasis - home on the Chesapeake Bay

Sleeps 5 · 2 bedrooms · 1 bathroom

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