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Originally built in the 1880's, the Hillcrest Hotel on Chebeague Island has been a vacation destination for well over a century. In the beginning of the 20th century, the original hotel burned down and was replaced in the 1920's by its current structure. In 2000, the Hillcrest Hotel was renamed Chebeague Island Inn. Over the years the Inn has played an important role in the island community and takes pride in being part of the island's storied history of sailing and architecture.

Chebeague (pron: shuh-Beeg) is one of Maine's most beautiful islands, home to generations of year-round and summer families. Chebeague Island has a storied history of sailing, notably the stone sloopers, men who carried ballast for the sailing ships of 19th century America and later granite for many of the country's most spectacular buildings, including the Washington Monument. The many lovely Greek revival homes on the island were built by these sloopers.