Search all holiday resorts in Chesapeake Beach, MD

This spacious 2,700+ sq ft apartment in North Beach is situated just four blocks from the waterfront and boardwalk, placing you within a 10-minute walk of the beach, shops, restaurants, and breweries, with a private two-car driveway offering rare convenience in this walkable community.
This four-bedroom, four-and-a-half-bathroom residence accommodates up to eight guests, featuring two primary suites, an upper-level bonus room, a rear deck for outdoor enjoyment, and a kitchen equipped with a fridge, freezer, microwave oven, and dishwasher, all supported by air conditioning and internet.

The North Beach Retreat House is situated in North Beach, Maryland, a short drive from Chesapeake Beach Water Park and the Chesapeake Beach Railway Museum.
This three-bedroom, three-bathroom property, sleeping up to nine guests, offers free Wi-Fi, air conditioning, and in-house laundry facilities within its 0.001 square kilometre floor area, and is close to Rod 'n' Reel Charter Fishing and Fridays Creek Winery.

This two-bedroom townhouse is situated in a peaceful neighbourhood just 1.6km from the North Beach boardwalk, offering a quiet escape from the bustling beachfront. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The house is ideal for families or groups of up to four guests, providing a private and spacious living area. Guests can enjoy a fully equipped kitchen, a basement with a pool table and comfortable seating, and a garden, alongside free parking for two vehicles.

The Cozy Crab apartment is situated in Calvert County, Maryland, a short drive from attractions such as the Rod 'n' Reel Charter Fishing and Fridays Creek Winery.
This one-bedroom, one-bathroom self-catering flat sleeps four guests and features a fully equipped kitchen with appliances including a fridge, microwave, and dishwasher, plus air conditioning, a garden, and parking.