City-dwellers looking to trade the swankiness of the Hamptons for something a bit more laidback generally head here. At its core, this lakeside escape caters to the surfer set, which explains the massive pileup of longboards. Though modest in size, the 19 guest rooms—complete with hanging egg chairs and luxe bedding—are the ideal home-away-from home. The in-room hammocks, beachside bonfires, and whitewashed wood flooring lend themselves nicely to the chill vibe of the place. But still, thanks to its close proximity to Montauk’s main drag, the late-night scene can get rowdy to say the least. In the capable hands of Executive Chef Rober Sieber, the The Surf Lodge Restaurant has earned a reputation for providing diners a fresh seafood-minded menu that features impressive fresh seafood towers and a signature lobster roll.

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