Osterville once had several historic inns and lodges that provided accommodations to visitors in the late 19th and early 20th centuries, taking advantage of the village's proximity to beaches, bays, and activities. Some of the largest inns included the West Bay Inn, East Bay Lodge, and Crosby House. These establishments offered meals, events, and views of the water but have mostly been lost to fires and redevelopment over the decades. Smaller lodging options also previously existed throughout the village.