I stayed at a 99-year-old hotel in Montauk for $490. It hasn't lost any of its 1920s charm.
Briefly

Montauk Manor opened in 1926 as part of Carl G. Fisher's early-1920s plan to make Montauk the "Miami of the North," with the hotel sited atop Signal Hill. The property later joined the National Register of Historic Places in 1984. The hotel combines historic architecture with modern amenities and offers duplex units with up to three bedrooms, ground-floor patios, and a U-shaped layout that limits some water views. An outdoor lounge overlooks the grounds. During August the property felt relatively quiet despite summer crowds, likely due to the estate's large size.
But that all began to change when a developer named Carl G. Fisher, the man responsible for building up Miami Beach, set his sights on Montauk. He planned to make the area the "Miami of the North," and bought some 9,000 acres of land to make that dream a reality in the early 1920s. Fisher's pièce de résistance was Montauk Manor, a hotel atop Signal Hill.
There's an outdoor lounge area right next to the entrance, where you can take in the views at all hours of the day. There was a volleyball net right in front of these chairs, but I never saw anyone using it. In general, even though I went in August, it seemed relatively quiet at the hotel. It was never empty, but it wasn't overwhelmingly crowded. I think the property's large size had something to do with it.
Montauk Manor has been a Hamptons institution since it opened its doors in 1926. During my stay in August, I was impressed by its modern amenities and historic architecture. In the nearly 100 years since it opened, it hasn't lost any of its '20s charm. Now, almost 100 years later, his plan seems to have worked, for the most part. Montauk is just as crowded as the Hamptons every summer, and his hotel remains open.
Read at Business Insider
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