About Cragston

Benjamin Chester has been hosting at Cragston, a historic estate in Highland Falls, New York, for two years. In that time he has welcomed families, reunion groups and corporate teams to The Main House. The house was once Billy Joel’s home and sits on the grounds of J.P. Morgan’s 1859 Cragston estate, looking out over the Hudson River. Benjamin keeps a perfect 5.0 rating across more than 100 guest reviews. Guests often mention how quickly he responds, how well the home is kept, and how carefully it is set up for large groups. The Main House sleeps up to 25 guests across seven bedrooms, and he can add the neighboring Carriage House for groups of up to 35. Benjamin also has a background in startups, which shapes how he hosts. He offers direct booking with clear, upfront pricing, 3D virtual tours so guests can check sleeping arrangements before they book, and quick communication from inquiry through checkout. His aim is a quiet, comfortable stay that lets groups focus on time together, just minutes from West Point and Bear Mountain State Park.