Ogelton Overlook

Welcome to Ogelton Overlook. This 5 bedroom / 5 bathroom Coastal Charm sleeps 14 comfortably. This thoughtfully stylish home overlooks the Bay and is your perfect Annapolis escape.

Nestled in a charming coastal neighborhood, this beautifully located home offers the perfect blend of relaxation, comfort, and classic Chesapeake Bay charm. Whether you're visiting for sailing, a weekend getaway, Naval Academy events, or simply to explore the historic waterfront, this home puts you right in the heart of it all. Step inside and feel instantly at home in a bright, welcoming space designed for comfort and relaxation. This inviting property offers the perfect setting for families, couples, and groups looking to experience Annapolis like a local.

Guests love the mix of comfortable living spaces perfect for relaxing after a day on the water. Thoughtfully designed interiors with coastal-inspired touches

Plenty of room to unwind, connect, and make memories. Whether you're enjoying morning coffee before a day of sailing or relaxing after exploring downtown, this home offers the ideal home base. Additionally, you'll have easy access to downtown Annapolis, a quiet neighborhood feel while staying close to everything and a relaxing place to unwind after a day of exploring.

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During your stay you'll be minutes from; the Historic downtown waterfront full of Sailing, Marinas, and Chesapeake Bay views. The local flavor full of incredible seafood restaurants and waterfront dining. Local boutiques for shopping, town favorite coffee shops, and art galleries. Naval Academy events and campus visits.

Spend your day exploring cobblestone streets, watching boats glide across the harbor, or enjoying famous Maryland crab cakes before returning to your peaceful retreat.

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We want every guest to have a 5-star stay. You'll enjoy:

Easy self check-in

Clear communication

Local recommendations

A clean, comfortable home prepared for your arrival

​​​​​​Book now and experience the charm, history, and coastal beauty of Annapolis from your own private retreat.