A Hamptons staple for over 150 years, The Maidstone has long drawn the city crowd with its classic white-shingled façade, black shutters, and billowy hydrangeas. But thanks to a Mediterranean-leaning revamp by LDV Hospitality, it now channels the spirit of the Italian Riviera: striped towels, tasselled parasols, Aperol on pour, and a standout spaghetti alla Nerano. Inside, the vibe is curated but relaxed, with olive trees, wicker accents, and a sunny palette that’s more Positano than prep. There’s serious fashion cred too: Sézane once popped up in the shop, a Gucci Airstream’s been spotted on the lawn, and the hotel merch is genuinely covetable. In a scene-y slice of Long Island, this 19-room stay keeps things effortlessly cool – and quietly elevated at that.