Chesapeake Beach Vacation Rentals

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Vacation Rentals in Chesapeake Beach

Sweet Bamboo Beach Cottage

north beach MD

When you stay at this vacation home in North Beach, you'll be on the beach, within a 10-minute walk of Bayside History Museum and Chesapeake Bay.

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Washer

Grace Cottage, Saint Michaels Walk to everything!

Saint Michaels MD

With a stay at this vacation home in St. Michaels (Downtown St. Michaels), you'll be steps from Muskrat Park and Saint Marys Square.

Charming Annapolis WaterVIEW Home

Annapolis MD

With a stay at this vacation home in Annapolis (Arundel on the Bay), you'll be steps from Chesapeake Bay and Northern Chesapeake Bay.

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Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views

Tilghman Island MD

When you stay at this vacation home in Tilghman, you'll be on the waterfront, just steps from Chesapeake Bay and Northern Chesapeake Bay.

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Washer

Amazing views waterfront 3-bedroom home in Madison with a 190 foot pier!

Madison MD

Located in Madison, this vacation home is on the waterfront, within a 15-minute drive of Blackwater National Wildlife Refuge and Harriet Tubman Underground Railroad National Historical Park.

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Washer

Mid-Century Modern on Private Beach, Designed by Award Winning Architect!

Chesapeake Beach MD

When you stay at this vacation home in Chesapeake Beach, you'll be on the beach, just steps from Chesapeake Bay and Northern Chesapeake Bay.

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Washer

GRATITUDE FARM - A Tranquil Waterfront Renovated Farmhouse - Bozman, MD

Bozman MD

Located in Bozman, this vacation home is on the waterfront, within a 15-minute drive of Neavitt Park and Perry Cabin Park.

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Secluded Woodland Waterfront Retreat

Solomons MD

This vacation home is 1.3 mi (2.2 km) from Annmarie Sculpture Garden and Arts Center and 1.4 mi (2.2 km) from Southern Branch Library.

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Private Cottage on gated estate

Annapolis MD

With a stay at this vacation home in Annapolis, you'll be within a 15-minute walk of Chesapeake Bay and Northern Chesapeake Bay.

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Washer

Mid-Century Modern Lake House – Gorgeous Fall Views, Fire pit, Sauna, 4BR

Lusby MD

Located in Lusby, this vacation home is a 5-minute drive from Chesapeake Bay and 6 minutes from Chesapeake Hills Golf Course.

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Washer

Waterfront Cheerful 6 BR Home with Private Pier

Edgewater MD

Located in Edgewater, this vacation home is on the waterfront, within a 10-minute drive of South River Golf Links and London Town.

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Washer

Million Dollar View of the Chesapeake Bay

Deale MD

Located in Deale, this vacation home is on the waterfront, within a 10-minute drive of Chesapeake Bay and Northern Chesapeake Bay.

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Washer

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.