Ira Foss built the Checkley House Hotel in the 1870s at the tip of Prouts Neck in Scarborough, later known as Checkley Point. The hotel was named after Samuel Checkley, one of the early settlers of Scarborough. The building started as a boarding house, expanding several times over the years until Mr. Foss's death in 1919. His widow ran the hotel after his death.

Mr. Foss was an innovative hotel owner. The water system he built for the hotel also benefited the neighboring homes. Mr. Foss purchased electrical generators for the hotel to provide power for his pumps and elevators and lighting before electricity was readily available. He supplied horse-drawn wagons to meet every train at the Scarborough Station to transport people to "the Neck."

The Foss family sold the hotel in the early 1940s. It was razed in 1944 after five years of blackouts and coastal evacuations caused by World War II.