USA Maryland Annapolis Listing #110378

The Pearl of Oyster Harbor - Annapolis, MD

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2 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 
Address provided after booking

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Expert cleaning

Pro housekeepers clean thoroughly and provide fresh linens before every stay.

Local support

Count on 24/7 guest care and local teams everywhere we operate.


Smart locks or lockboxes at many homes offer smooth, contactless check-in.

Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard

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

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. 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

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


2 reviews