A river with a bridge, marina, and residential area.

Chesapeake City cottage rentals

We found 12 cottage rentals — enter your dates for availability

Explore Chesapeake City cottage rentals

Image of Waterfront Cottage on the C&D Canal!

Waterfront Cottage on the C&D Canal!

Sleeps 4 · 1 bedroom · 1 bathroom

Image of Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

Premier Host

Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

Sleeps 6 · 2 bedrooms · 1+ bathroom

Image of The Cove On The Waterfront

Premier Host

The Cove On The Waterfront

Sleeps 8 · 3 bedrooms · 2 bathrooms

Image of Private Carriage House Retreat on a 33 Acre Historic Working Estate

Private Carriage House Retreat on a 33 Acre Historic Working Estate

Sleeps 8 · 2 bedrooms · 2 bathrooms

Image of Waterfront Home, Private Dock, A/C, Amazing Views, Boating, Fishing & Kayaking

Waterfront Home, Private Dock, A/C, Amazing Views, Boating, Fishing & Kayaking

Sleeps 4 · 2 bedrooms · 1 bathroom

Image of Chesapeake City Pool Retreat – Waterfront Stay in the Woods

Chesapeake City Pool Retreat – Waterfront Stay in the Woods

Sleeps 7 · 2 bedrooms · 1+ bathroom

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Enjoy full kitchens, laundry, pools, gardens and more
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