Our Story

The Dockside Inn has been a staple of the Oak Bluffs harbor for decades. Since taking ownership 15 years ago, John and Caleb have thoughtfully shaped the property into a boutique hotel experience that reflects both modern comfort and classic Martha’s Vineyard charm.

Their hands-on approach, attention to detail, and commitment to genuine hospitality can be felt throughout the inn — from the award-winning design to the welcoming service guests experience during every stay.

Whether you’re visiting for a romantic getaway, a family vacation, or a special event, John, Caleb, and the Dockside Inn team are here to make your island experience unforgettable.