The Hamptons Hotels

Establishment neighborhood
290 Old Montauk Hwy., Montauk
Thanks to a recent face-lift, this large resort in Montauk, which ranges along a prime slice of beach, is a good option, particularly 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—just be sure to request a renovated room.
1770 House
143 Main St., East Hampton
While it sits steps from East Hampton’s boutique-and-gallery-packed main drag, entering this six-room inn (there’s also a separate two-family carriage house) is a lot like stepping into a time machine. The picket-fenced, whitewashed home has functioned as a hotel since—you guessed it—1770. Alongside modern additions like in-room flat-screen TVs, its beautiful Colonial flourishes—exposed-wooden beams, antique fireplaces—are perfectly intact. We go for the ever-reliable and delicious burgers at the on-site tavern.
The Maidstone
207 Main St., East Hampton
Longtime owners Jenny and Jonathan Baker recently revamped their East Hampton destination hotel. The refreshed design lends a whimsical look to the traditional American aesthetic of the shared rooms, including the bar, lounge, and sunroom. We love how each of the nineteen guest rooms is individually designed, making you feel as if you're staying at your friend's summer house. Complete with a new restaurant from Chef David Strandridge of Cafe Clover, it is hands down an excellent place to visit or stay. Interior photos: Fran Parente.
The Crow’s Nest Inn
4 Old W. Lake Dr., Montauk
This fourteen-room hideaway is removed enough from the crush of Montauk crowds but an easy bike ride away from town when you need it. As for the design? 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 as 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). During the day, a small but thoughtful breakfast spread includes fresh berries, croissants, coffee, and a stack of New York Timeses; come evening, grab a table at the on-site Mediterranean-inflected restaurant, which serves up everything from curried vegetable ragout and blue crab claw tagliatelle to fresh whipped ricotta and local kale salad. Stop by Melet Mercantile, a jewel-box-size outpost of the vintage connoisseur's Manhattan outpost, for an expertly curated…
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.