The Pearl of Oyster Harbor - Annapolis, MD

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

• Check-in time: 4:00 p.m.
• Check-out time: 10:00 a.m.
• All guests shall abide by Vacasa’s good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.
• No smoking is permitted anywhere on the premises.
• This home is dog-friendly, but only 2 dogs are allowed per reservation. Neighbors are uber-sensitive to barking and off-leash dogs, so please be pet-friendly to neighbors. Keep your dogs on a leash when outdoors. Please do not leave dogs in the yard unattended. Dogs must also be crated in the street-facing bedroom if you leave them alone in the house.

• 2 dogs welcome in this home. No other animals are allowed without specific Vacasa approval.
• Parking notes: There is free parking available for 4 vehicles.
• Guest entry instructions: This rental utilizes an E-lock, a digital lock that requires a unique code to enter. This code is reset after each guest's stay.
• Security camera details: Front door and towards dock

County permit number: STR346

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