Chesapeake Beach Vacation Rentals

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Vacation Rentals in Chesapeake Beach

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

North Beach MD

Located in Owings, this vacation home is within a 5-minute drive of Bayside History Museum and Chesapeake Bay.

Kitchen

Air conditioning

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

St. Michaels MD

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

Kitchen

Washer

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Prince Frederick MD

$384 nightly

$407 total

Jan 6 - Jan 7, 2026

Total with taxes and fees

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

Kitchen

Washer

Edgewater/Mayo Gateaway w/ Hot Tub

Edgewater MD

With a stay at this vacation home in Edgewater, you'll be within a 10-minute drive of Chesapeake Bay and Northern Chesapeake Bay.

Hot Tub

Kitchen

Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis

Annapolis MD

With a stay at this vacation home in Annapolis (Cape St. John), you'll be within a 15-minute drive of U.S. Naval Academy and Annapolis Harbour Center.

Pool

Kitchen

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Port Republic MD

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

Kitchen

Washer

Discover tranquility near Calvert Cliffs

Saint Leonard MD

Located in St. Leonard, this vacation home is on the waterfront, within a 10-minute drive of Perigeaux Vineyards and Winery and Jefferson Patterson Park and Museum.

Kitchen

Washer

Midcentury Modern Lake House, gorgeous views, deck, 4-bedrooms in Lusby/Solomons

Lusby MD

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

Kitchen

Washer

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Prince Frederick MD

$344 nightly

$365 total

Dec 18 - Dec 19

Total with taxes and fees

Located in Prince Frederick, this vacation home is near the beach, within a 5-minute walk of Chesapeake Bay and Northern Chesapeake Bay.

Kitchen

Washer

Heart of Tilghman Island | Pet Friendly | Perfect for Weddings Guests & Families

Tilghman Island MD

With a stay at this vacation home in Tilghman, you'll be within a 5-minute walk of Talbot County Library Tilghman Branch and Tilghman Watermen’s Museum.

Kitchen

Washer

Beautiful 2-bedroom water view house in Annapolis

Annapolis MD

With a stay at this vacation home in Annapolis (Arundel on the Bay), you'll be within a 10-minute walk of Chesapeake Bay and Northern Chesapeake Bay.

Washer

Dryer

Holly Hill Haven - Sleeps 10

Edgewater MD

Located in Edgewater, this vacation home is within a 10-minute drive of South River Golf Links and Chesapeake Bay.

Kitchen

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.