Eastport Bungalow | Yard, Grill & Walk Downtown

Welcome to The Captain's Quarters, a beautifully restored 4BR/3BA home in the heart of walkable, historic Eastport. Old-world craftsmanship meets thoughtful modern (and sustainable) updates—wood floors, wood furnishings, and curated nautical artwork throughout. Enjoy the front porch, back patio, plus a fenced, dog-friendly backyard. Sleeps 8. Free parking. Friendly Navy/Marine neighbors and unbeatable location—everything is just steps away.

Charming 1920s Bungalow in Eastport – Walk to Downtown Annapolis

About the Space:
-Unique, restored bungalow in the heart of Eastport’s maritime district
-Just one mile to Downtown Annapolis, City Dock, Naval Academy, and the State House
-Historic charm meets modern comfort with wood floors, antique decor, and nautical touches
-Ideal for families, small groups, or those seeking a cozy getaway

Living Spaces:
Main Room:
-Filled with maritime-themed decor and eclectic character
-Drum set for music lovers
-Futon sofa and armchair


Second Living Room:
-Perfect for reading or intimate gatherings
-Desk with maps and books for exploration
-Flows into the dining room and fully equipped kitchen

Outdoor Oasis:
-Sliding door from the kitchen leads to a large, private fenced-in yard
-Organic garden with fig and pawpaw trees
-Two small ponds (one in the front)
-Patio with a grill, chiminea, lawn furniture, and shade trees
-Eco-friendly landscaping for a sustainable retreat

Bedrooms & Bathrooms:
First Floor:
-Queen bedroom with attached bathroom and shower
Second Floor:
-Three bedrooms, each with a queen bed
-Hall bathroom with a stand-up shower
-Primary suite has a queen bed and private bathroom with a large soaking tub and hand-held showerhead

Eco-Friendly Features:
-Rooftop solar panels for sustainable energy
-Permeable gravel driveway for environmental benefits
-Energy-efficient tankless water heater means you'll never run out of hot water!
-Composting and recycling encouraged

Amenities & Conveniences:
-One off-street parking space; free on-street parking available
-Ceiling fans, central AC, and complimentary WiFi
-Two smart TVs for entertainment
-Two office spaces with desks and chairs – great for remote work
-Books on sailing and local culture for curious minds

Pet Rules
-Guests must disclose pets at the time of booking.
-Guests may bring up to 2 dogs who weigh 60 lbs or less each.
-Guests must keep dog(s) leashed when outside of the home or yard.
-Dog(s) are not permitted on beds/couches/chairs.
-Guests must clean up pet waste.

Getting Around:
-Most Annapolis attractions within walking distance
-Water Taxi Nearby:
-Just a 3-minute walk to the South Annapolis Yacht Center pickup spot (750 Boucher Ave.)
-A scenic ride to Annapolis City Dock with optional dockside pickups along the way
-Ask your Water Taxi Captain for local tips and recommendations!

We’ll follow up with a short online registration once you book. It’s fast, simple, and helps us prepare for your visit. Non-Airbnb guests will be asked to pay a small damage waiver OR refundable deposit.