Experience the Difference: Professionally Managed by iTrip Annapolis

Waterfront Oasis with Private Dock, Firepit & Kayaks

Welcome to the Pearl of Oyster Harbor – a tranquil waterfront retreat on the Annapolis Neck Peninsula. This charming cottage offers the best of all worlds: stunning natural beauty, water activities, and modern comforts.



Outdoor Features:

Private dock for boating, kayaking (3 total kayaks: two adult and one youth), or paddleboarding (inflatable SUP included)

Expansive lawn perfect for cornhole, yard games, or simply soaking up the view

Firepit for cozy evenings with s'mores and stories

Hammock for relaxing with a good book or simply enjoying nature

Parking for 3-4 cars on the driveway



Indoor Highlights:

Bright, airy sunroom with harbor views for board games and family time

Sleek, modern kitchen with large picture windows framing the waterfront

Living room featuring a smart TV and gas fireplace for cozy evenings

Small desk and WiFi printer for remote work convenience



Neighborhood amenities:

Swimming beach

Exercise: Beach volley ball court, 1-mile exercise circuit course, 12' climbing wall, 16' rope climb,

Fishing pier and boat ramp

Playgrounds, nature preserve, picnic areas, beach gazebos



Starter Amenity Pack:

We've got you covered with essentials to make your stay stress-free, including:

Coffee, sweeteners, dish soap, and paper towels

Soap, shampoo, conditioner, and hand sanitizer

Freshly-laundered sheets and towels for every guest



Sleeping Arrangements (3 BR / 2 BA, Sleeps 8):

Front Queen Bedroom: Queen bed, shared full bath in the hall

Waterfront Bedroom: Full bed, shared full bath in the hall

Bunk Bedroom: Twin bunk beds (two twins), shared hall bath

Loft: Full bed above the living room



House Rules:

Family rentals only; one guest must be at least 25 years of age

No smoking, parties, or events

Quiet hours from 9:00 pm to 8:00 am

Dogs allowed with $150 per pet non-refundable fee paid prior to checkin.

Check-in: 4:00 pm | Check-out: 11:00 am



Property Distance to:

-Downtown Annapolis – 4 miles (10 mins)

-U.S. Naval Academy – 4.5 miles (12 mins)

-Washington, DC – 35 miles

-Baltimore - 20 miles



Create lasting memories at The Pearl (of Oyster Harbor), where waterfront tranquility meets thoughtful amenities and outdoor fun. Book your stay today for an unforgettable Chesapeake Bay escape!