The Pearl of Oyster Harbor - Annapolis, MD

Welcome to The Pearl of Oyster Harbor, managed by Vacasa. This house is located in Annapolis but your 24/7 support is always nearby.

This house features 3 bedrooms and 2 bathrooms with space enough for 8.

Please review our property photos and our available amenities to make sure this rental is a perfect fit for your needs. We strive to keep this information as up-to-date as possible so you can feel confident in knowing what you are renting.

We will send you all necessary pre-arrival and check-in information after booking. This can include guest instructions, notices, and other helpful information.

What We Love

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. Bonus features include a washer/dryer and a small desk in the bunk room - with a WiFi printer - that's perfect for remote work.

House Rules

• Streaming services are available with guests' own account credentials.
• Check-in time: 4:00 PM.
• Check-out time: 10:00 AM.
• All guests shall abide by Vacasa's good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AM.
• No smoking is permitted anywhere on the premises.

• 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

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