The Hamptons Hotels
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 the in-room iPad docks and flat screens, its beautiful Colonial flourishes—exposed wooden beams, antique fireplace—are perfectly intact. We go for the ever-reliable and delicious burgers at the on-site restaurant.
31 W. Water St., Sag Harbor
Once the preferred hangout of Truman Capote, Jackson Pollock, and Kurt Vonnegut, Baron's Cove is back to its former glory after a two-year renovation (completed in 2015). This historic, sprawling, whitewashed spot is now home to 67 plush rooms (there's a subtly nautical theme throughout), plus a massive pool, gym, and excellent seafood-centric restaurant.
290 Old Montauk Hwy, Montauk
Thanks to a recent face-lift, this big 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 kid's club, a beach club, and all the amenities you'd expect from a mainland hotel, like free Wifi, 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.
Hero Beach Club
626 Montauk Hwy, Montauk
As Montauk's popularity continue to swell, this clean-lined, boutique resort caters to families, tourists, and anyone looking to explore the area: The hotel staffs resort offers bespoke concierge service to help you create a unique Hamptons experience– whether it be filled with hiking and exploring outdoors or trying the local hotspots. We especially love its mid-century-meets-modern aesthetic and family-friendly ethos.
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. Owned by André Balazs, Sunset Beach Hotel sidles right up next to the ocean, with just 20 guest rooms that all have private porches looking out onto the water. Like any Balazs hotel, the food (and especially drink) 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 blessedly easy here—bikes are complimentary, and the hotel will happily arrange for beach chairs, paddle boards, and boats so guests can waterski, fish, or generally explore the area by water. Good to know: Since the beach here is west-facing, it's a great place to watch the sunset.
23 Grand Ave., Shelter Island Heights
After a grand re-opening following a major renovation, The Chequit is officially on our Hamptons short-list. The 37-room hotel feels more like a bed and breakfast, which is good since a glitzy resort wouldn't feel at all right on quaint Shelter Island. The rooms are equipped with all the amenities you'd want, without sacrificing any of the charm of this 121-year-old property. Like a proper inn, breakfast is served every morning in the beautiful lobby. But if getting up sounds like too much work, they'll serve you coffee and pastries in bed. Red Maple, the hotel's full-service restaurant, serves weekend dinners and an a great Sunday brunch on a patio that overlooks the water. For something lighter, White Hill Cafe has great pastries and sweets (ask them to put together a to-go picnic before heading to the beach) and connects to Jack's Stir Brew coffee bar.
The Crow’s Nest Inn
4 Old West Lake Dr., Montauk
The 14-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 considered from the crisp Indian-inspired John Robshaw bedding and shibori-dyed throw pillows to a fridge stocked with Tate's Bakeshop cookies and Wölffer rosé. For families traveling together, or for those seeking a bit more space, the collection of David Pharaoh Cottages are a solid option since 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 the New York Times; 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-boxed sized outpost of the vintage connoisseur's Manhattan outpost, for an expertly curated selection…
The Inn at Windmill Lane
23 Windmill Ln., Amagansett
This is a luxurious inn with elegant rooms that's more of a quiet couple's retreat than a family spot. If you're traveling with a group, though, ask about 21 House, their four-bedroom private home, which comes with all the amenities of the larger inn (housekeeping, gym, transportation) and is available for private rentals.
207 Main St., East Hampton
Longtime owners Jenny and Jonathan Baker have revamped their East Hampton destination hotel this summer. The refreshed design lends a whimsical look to the traditional American aesthetic of the shared rooms, including the bar, lounge, and sun room. We love how each of the nineteen guest rooms are individually designed, making you feel like you're staying at your friend's summerhouse. Replete 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 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.
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