USA Maryland Annapolis Listing #110378

The Pearl of Oyster Harbor - Annapolis, MD

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13 reviews
Max. occupancy: 8 1 queen bed, 2 double beds, 1 twin bed, 1 twin upper bunk bed 3 bedrooms plus loft 2 bathrooms 2 dog max 
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Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard

Whether it's relaxation or activity you seek, you'll find it all in the gorgeous waterfront setting of The Pearl of Oyster Harbor. This is a stunning place for boating and swimming from the private dock, playing yard games at the water's edge, and gathering around the firepit for s'mores and stories once the sun goes down.

This peaceful, two-story home boasts an expansive piece of property in Oyster Harbor, a private community on the Annapolis Neck Peninsula along an inlet of the Chesapeake Bay. The flat, beautiful lawn stretches all the way to the dock, where you're welcome to tie up your boat, launch one of the kayaks (two adult, one youth), or take out the inflatable paddleboard. (The bay can be shallow and tricky in parts; please familiarize yourself with the water before you navigate a boat.)

When you're not strolling less than half a mile to Oyster Harbor Private Beach, make a day of it in the backyard by playing cornhole, yard toss, or Slip-N-Slide. Light the gas grill for a lunchtime barbecue, dine in the coastal breeze on the deck or at the picnic table, and linger all afternoon in the hammock while watching passing boats, birds, and marine life.

Built in 1960 and thoughtfully renovated in the years since, this unique cottage maintains much of its original character while offering modern touches at every turn. Large picture windows and rear glass doors frame the harbor - a lovely view you can take in as you cook in the sleek kitchen, make plans over breakfast each morning, and play board games and cards in the sunroom. In the evenings, enjoy an inviting living room with a smart TV and gas fireplace, three cozy bedrooms, and a sleeping loft. The small desk in the bunk room has a WiFi printer, making it perfect for remote work.

Things to Know

County permit number: STR346

You must be 25 years or older to rent this property.




Heating & cooling

Central AC


Partial AC

Gas fireplace

House rules


Kitchen & dining






Water view






Wireless router

Netflix streaming

Nearby activities & attractions


On-site activities

Adult bikes

Board games



Gas grill : Private




Enclosed yard


Map showing the location of the Unit

13 reviews