07/28/2026
Hi, I’m Shawn—the owner and longtime caretaker of Chesapeake Paradise.
This place has grown slowly, thoughtfully, and one space at a time.
It began in 2009 with the upstairs Flat, which I renovated as a private waterfront apartment where people could retreat, settle down, and simply breathe. That one special stay later became known as Maryland’s most wished-for Airbnb by Travel + Leisure magazine.
As more guests came—and more families wanted to gather here—I began transforming the rest of the property. The whole house, once known as Light Landing, was completely transformed into Chesapeake Paradise—expanded, modernized, and reimagined around the water,
More recently, the little cottage next door received a beautiful new open-concept kitchen, along with a bay-window upgrade in the waterfront bedroom that created a cozy place to sit, read, and take in the view—all while keeping the quaint, cottage-like character that makes it feel so welcoming.
That blend of old and new is part of what makes Chesapeake Paradise feel the way it does. Some spaces are fresh and modern. Others are cozy, familiar, and full of history. All have been shaped with care.
I’ve always believed this place offers more than a beautiful view or somewhere comfortable to sleep. There is something about the water, the wide-open sky, and the quiet here that helps people soften a little. Families reconnect. People open up and breathe deeper without even realizing it.
Creating that kind of experience—and continuing to tend it with care—is one of the great joys of my life.
So when you stay at Chesapeake Paradise, you are not booking with a large rental company. You are stepping into a place that has been built, renovated, loved, and shared by a real person who genuinely wants you to feel at home here.
