The Hamptons Hotels

Establishment neighborhood
Sunset Beach
35 Shore Rd., Shelter Island
Just north of most of the action, Shelter Island remains one of the quieter parts of the Hamptons—cynics would say it's a bit like Montauk in the old days, before real estate values in the area exploded. André Balazs's Sunset Beach Hotel sidles right up next to the ocean. The 20 guest rooms all have private porches looking out onto the water. As at any Balazs hotel, the scene is on point, with a great little European-style restaurant and a bar that offers some of the area's best DJs. Easy access to the beach also makes activities here especially nice—bikes are complimentary, and the hotel will happily arrange for beach chairs, paddleboards, and boats so guests can water-ski, fish, or explore the area by sea. Good to know: The beach here is west-facing, so it's a great place to watch the sunset.
Gurney’s Montauk Resort & Seawater Spa
290 Old Montauk Hwy., Montauk
This large resort in Montauk, which ranges along a prime slice of beach, is a good option if you have kids or a bigger group. Beyond a spate of great restaurants (Tillie's, Scarpetta, a coffee shop in the lobby), there's a kids’ club, a beach club, and all the amenities you'd expect from a big hotel, like free Wi-Fi, a gym, a pool, and a spa. It's also one of the area's only year-round resorts, which is great if you're hoping to make a visit during the quieter spring or fall months.
The Crow’s Nest Inn
4 Old W. Lake Dr., Montauk
This 14-room hideaway is removed enough from the crush of Montauk crowds but an easy bike ride away from town when you need it. It's the brainchild of hotelier Sean McPherson (of the Bowery and the Marlton fame), which means every detail has been carefully considered, from the crisp Indian-inspired John Robshaw bedding and shibori-dyed throw pillows to the fridges stocked with Tate's Bakeshop cookies and Wölffer Estate rosé. For families traveling together or those seeking a bit more space, the collection of David Pharaoh Cottages are a solid option; each has its own kitchenette, daily housekeeping, and a beach parking pass (clutch if you've ever brought a car out to Montauk in the summer). Come evening, grab a table at the on-site Mediterranean-inflected restaurant. Stop by Melet Mercantile, an outpost of the vintage connoisseur's Manhattan store, for an expertly curated selection of beach-centric vintage books, magazines, and a small collection of clothing, as well cheeky cashmere sweaters from the label Lingua Franca, designed by McPherson's wife. Don't miss the s'mores by the firepit or the lounge chairs overlooking Montauk Harbour.
The Montauk Beach House
55 S. Elmwood Ave., Montauk
This is the kind of convivial, party-prone place you want to go with your whole crew—in fact, it's pretty much the heart of Montauk's social scene. Need proof? The events calendar is loaded with activities that range from morning zen sessions to live tattooing to poolside socials. If and when shuteye is required, the vintage-themed guest rooms are meant to be shared—plus, they're equipped with beds so fluffy you'll gladly sleep through prime pool time.