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We get it: You love your corner of the Hamptons. But sometimes you need to change things up. And the easiest way to do that is to venture to nearby Shelter Island and check in to the Chequit. Let us explain...

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The historic whitewashed 37-room inn is the stuff summer dreams are made of. Originally a religious retreat in the 19th century, it later evolved into a hotel that served as a vacation spot for the rich and famous (think Frank Sinatra and Marilyn Monroe).

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Today, it has been revamped with lots of perks and amenities. Guests can get breakfast in bed (baked pastries, house-made granola, a variety of savory dishes and more--all with no delivery charge) or enjoy the lush spread in the sunny lobby, which later in the day is transformed into a guests-only wine and Champagne lounge that spills out onto the porches overlooking the harbor.

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Parking and Wi-Fi are also gratis, and an on-site café stocks coffee, pastries and healthy house-made foods, all of which are packaged to be picnic-ready. You’ll also find a retail store with skate- and surf-inspired clothing


Red Maple--the bar and restaurant serving rustic, locally sourced small plates and flatbreads--just opened on the property.

23 Grand Avenue, Shelter Island Heights, 631.749.0018. Rooms start at $195.

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