Perhaps the most famous hotel in Sag Harbor is the American Hotel, with a prominent Main Street location. Addison Youngs and his father-in-law Captain William Freeman opened the American Hotel in 1877, as on the first hotels on Long Island to offer the conveniences of electric lights, steam heating, and indoor plumbing. Previously, the building existed as a commercial space for furniture-maker Nathan Tinker, on the site where James Howell operated an Inn in the pre-revolutionary period. The structure that currently stands is not pre-revolutionary, and it reflects construction after the 1845 fire. It reflects the c. 1880 expansions and additions of Addison Youngs. These expansions included the iconic front porch, which is now a popular dining area.
Also near the American Hotel was the Mansion House, located in the present-day municipal building. Built in 1846, in the glory days of the whaling industry, the Mansion House also provided a free carriage service to the steamboats. The Mansion House hotel included several shops. One of the shops was the pharmacy operated by local anthropologist-historian-pharmacist-photographer William Wallace Tooker.
Near the present-day Corner Bar, the Oakley family built an expansion of their Nassau Hotel. However, the Nassau Hotel caught fire in 1854, and by 1859 the Oakley family had to auction the hotel. The new owner continued to operate a hotel under the name Nassau House on the site. Other fires and remodeling influenced the ownership and façade of the hotel. By 1894, Nassau House was remodeled into the four-story building with modern utilities remembered as the Hotel Bayview.
This image of the Hotel Bayview was published in Dorothy Zaykowski’s book, it originally came from the collection of Otto Fenn.
Several boardinghouses operated in the village during the 19th century, including a few that catered to specific summer clientele, like the Lobstein House, the Lily Pond House, the Lundhurst Hotel, and the East End Hotel, and the Bijou Hotel. From 1891 until 1970, the preferred summer accommodations for the wealthy and celebrities was actually on Brickkiln Road outside the village. This hotel was called the Sea View Hotel (later Hill Top Acres) operated on Brickkiln Road.
For the less famous, Hedges House opened in 1817, across from the Nassau Hotel, catering to sailors during the heyday of the whaling industry. Betsy Josie also operated a boarding house on Meadow Street, in the path of the railroad. Her fight with the Long Island Railroad is featured in SHHS’s current exhibit on the Long Island Railroad in Sag Harbor.