The Pearl of Oyster Harbor - Annapolis, MD

Max 8 guests 3 bedrooms 2 baths Dog-friendly 
What our guests are saying...
Diamond AI-generated from guest reviews for this property
The property offers a beautiful and well-lit living space with stunning water views, creating a pleasant atmosphere during sunrise and sunset. It is centrally located, providing easy access to downtown Annapolis and USNA, making it ideal for sightseeing and relaxation. Guests appreciate the ample space and comfortable accommodations, including a lovely outdoor area with a deck, yard, and dock, perfect for gatherings and enjoying the scenery. The house is clean, organized, and charmingly decorated, filled with thoughtful touches that enhance the welcoming ambiance. The well-equipped kitchen and availability of various games and sports equipment contribute to a fun and enjoyable stay. Overall, the property provides a positive experience with its beautiful views and convenient location. Read more
See location on map Address provided after booking

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.

HOUSE AMENITIES

Features

Iron

Heating & cooling

Central AC

Fireplace

Partial AC

Gas fireplace

House rules

Dog-friendly

Kitchen & dining

Dishwasher

Fridge

Microwave

Stove

Location

Water view

Waterfront

Media

Internet

TV

Cable

Wireless router

Netflix streaming

Nearby activities & attractions

Dock

On-site activities

Adult bikes

Board games

Kayaks

Outdoor

Gas grill : Private

Patio

Deck

Firepit

Enclosed yard

Hammock

Map showing the location of the Unit

23 reviews

4.65