Chesapeake Beach Vacation Rentals

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Vacation Rentals in Chesapeake Beach

Dollhouse in Central Historic St Michaels

St Michaels MD

With a stay at this vacation home in St. Michaels (Downtown St. Michaels), you'll be within a 5-minute walk of Muskrat Park and Higgins Yacht Yard and Marina.

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Washer

The Blue Crab Beach House - Free beach passes

North Beach MD

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

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Washer

The Cozy Crab- Your Charming Haven in Lovely North Beach!

North Beach MD

With a stay at this vacation home in Owings, you'll be within a 5-minute drive of Chesapeake Bay and Bayside History Museum.

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Air conditioning

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

"La Licorne" Waterfront Beach Cottage

North Beach MD

With a stay at this vacation home in North Beach, you'll be steps from Chesapeake Bay and Northern Chesapeake Bay.

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Washer

Secluded Woodland Waterfront Retreat

Solomons MD

This vacation home is 6.3 mi (10.1 km) from Chesapeake Bay and 1.3 mi (2.2 km) from Annmarie Sculpture Garden and Arts Center.

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Beautiful 3 Bedroom Retreat walking distance to Downtown St. Michaels

Saint Michaels MD

A stay at this vacation home places you in the heart of St. Michaels, within a 10-minute walk of Classic Motor Museum and Windon Distilling.

Kitchen

Washer

Pool & Yard Retreat | 4BR | 20 Min to Annapolis

Harwood MD

This family-friendly vacation home is 12.3 mi (19.8 km) from Chesapeake Bay and 13.4 mi (21.6 km) from U.S. Naval Academy.

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Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Tilghman Island MD

When you stay at this vacation home in Tilghman, you'll be on the waterfront, within a 15-minute walk of Chesapeake Bay and Northern Chesapeake Bay.

Kitchen

Washer

Grace Cottage, St Michaels Walk to everything!

Saint Michaels MD

A stay at this vacation home places you in the heart of St. Michaels, steps from Muskrat Park and Saint Marys Square.

Washer

Dryer

Cozy Cottage By The Beach-Pet Friendly

North Beach MD

With a stay at this vacation home in North Beach, you'll be within a 15-minute walk of Chesapeake Bay and Bayside History Museum.

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Washer

Luxury modern mansion/Cabin Near Washington DC-on over 4 Acres of private land.

Upper Marlboro MD

With a stay at this vacation home in Upper Marlboro, you'll be within a 15-minute drive of Northwest Stadium and Liberty Sports Park.

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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.