The Hamptons Hotels

Here, along Montauk's Umbrella Beach, each of the 34 bedrooms features tastefully beachy furnishings imported from Bali, the kind of mattresses you'd happily spend the weekend lounging on, and crisp linens from Hill House Home. (Several of the rooms also have balconies.) In the morning, there's a small breakfast setup (bagels, coffee) but not too many other frills—and that's kind of the point. The delightfully in-the-know hotel staff will help with everything from, say, setting you up with surf lessons to tipping you off to the best lobster shack in town.

There’s a rich history behind the grounds and building of this temporary hotel: It formerly housed the Village Latch Inn and the Grand Annex to the Southampton Irving Hotel in the early 1900s. The cabanas and rooms are newly refurbished in a clean grey-and-white palette. Set on five acres with an expansive yard, it is a relaxing, no-frills place to stay within walking distance of Southampton’s shops and restaurants.

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.

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.

While it sits steps from East Hampton’s boutique-and-gallery-packed main drag, this six-room inn (there’s also a separate two-family carriage house) is charming, quiet, and old-school. The picket-fenced, whitewashed home has functioned as a hotel since—you guessed it—1770. Its beautiful Colonial flourishes—exposed-wooden beams, antique fireplaces—are intact, alongside modern additions. At the on-site tavern, go for the burgers.

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.

When longtime owners Jenny and Jonathan Baker revamped their iconic East Hampton hotel, they infused the traditional American aesthetic of the shared rooms, including the bar, lounge, and sunroom, with a dose of whimsy. Each of the 19 guest rooms is individually designed; it feels as if you're staying at your friend's summer house.

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.

This luxurious inn with spare, elegant rooms, soaring ceilings, tiled fireplaces, and super-indulgent bathrooms is a quiet retreat that’s private enough to work as a couples’ or family getaway. The comfy living areas are stocked with thoughtful snacks and strewn with coffee-table books. The gardens are beautiful—perfect for a wedding or gathering. If you're traveling with a group, ask about 21 House, the four-bedroom private home, which comes with all the amenities of the larger inn (housekeeping, gym, transportation) and is available for private rentals. They're hosting a pop-up of Manhattan and LA's Remedy Place in August.

The Topping Rose House is a beautifully restored nineteenth-century Greek revival inn located on a one-acre working farm.