Deale Beach Vacation Rentals

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Vacation Rentals in Deale Beach

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Annapolis MD

A stay at this vacation home places you in the heart of Annapolis, within a 10-minute walk of U.S. Naval Academy and Ellen O. Moyer Nature Park at Back Creek.

Kitchen

Washer

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

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Annapolis MD

This vacation home is in the heart of Annapolis, within a 10-minute walk of Maynard-Burgess House and U.S. Naval Academy.

Kitchen

Washer

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

Annapolis MD

With a stay at this vacation home, you'll be centrally located in Annapolis, within a 5-minute drive of U.S. Naval Academy and Annapolis Harbor.

Pool

Kitchen

Charming garden row home, easy 4 block walk to the heart of Annapolis.

Annapolis MD

With a stay at this vacation home in Annapolis (Historic District), you'll be within a 5-minute walk of U.S. Naval Academy and Hammond-Harwood House.

Kitchen

Washer

Location is perfect and a big bonus we have our own parking at the home!

Annapolis MD

With a stay at this vacation home in Annapolis (Historic District), you'll be within a 10-minute walk of U.S. Naval Academy and 97, 99 and 101 East Street.

Kitchen

Washer

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

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

Crofton MD

A stay at this vacation home places you in the heart of Crofton, within a 5-minute drive of Walden Golf Club and Regal Waugh Chapel.

Kitchen

Washer

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

Prince Frederick MD

$402 nightly

$426 total

Jan 8 - Jan 9, 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

Gather, Relax & Explore — Townhome 1 Block from State Capitol Building with Backyard & Parking

Annapolis MD

With a stay at this vacation home, you'll be centrally located in Annapolis, within a 5-minute drive of U.S. Naval Academy and Annapolis Civil Rights Plaque.

Kitchen

Washer

Edgewater/Mayo Gateaway w/ Hot Tub

Edgewater MD

$658 nightly

$713 total

Jan 8 - Jan 9, 2026

Total with taxes and fees

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

Luxury Waterfront Executive Family Home Annapolis with All Amenities

Annapolis MD

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

Hot Tub

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.