Stay in Osterville from Town and Country
With neither a hotel or inn to be found here, and precious little even in the way of Airbnbs, those who know Osterville will suggest turning to realtor Michelle Sylvia to secure a week, or more, in one of the exclusive seaside private residences she represents. One particular standout: Bunny Mellon’s former six-bedroom estate, where two cottages are nestled among beautiful gardens. (Her BFF Jackie Kennedy was a frequent visitor.) Sylvia’s ace concierge team can have the fridge stocked with all your favorites before arrival, set you up with a great private chef, organize golden hour family photoshoots, and, especially key here, arrange access to locals-only beaches.
By Andrew Sessa Published: Jul 27, 2025