Another colonial charmer, the 1708 House dates back to the eighteenth century and four of the rooms retain period details, including exposed ceiling beams, clawfoot tubs and period furnishings provided by 1708 House Antiques—a boutique also owned by the innkeepers, Skip and Lorraine Ralph. The rest of the B&B’s 14 rooms are newer, though wooden floors, antique furniture and Persian rugs maintain the historical atmosphere. All guestrooms, though, have been updated with modern luxury amenities like plasma TVs, Ralph Lauren linens and radiant tile heating in the bathrooms. In the back garden area, there are three 2-bedroom cottages, two of which have their own private kitchens. The cottages, which are ideal for small families as children under twelve are not allowed to stay in the main house, have a beachier feel with lighter woods and fewer antiques. The B&B’s convenient location steps from Main Street, right next door to Saks Fifth Avenue a block away from the shops and restaurants of Job Lane. The actual beach, though, is a good 20-minute walk away so if you’re lucky enough to score a room here, you should still bring (or rent) a car.

The 1770 House, like many Hamptons hotels, was built in the colonial period (in 1663 actually) and you’ll find antiques and exposed wooden ceiling beams located throughout the building. A 2002 renovation gave the property a fresher look and the six guest rooms are both rustic and chic, with paisley wallpaper, elegant curtains and headboards and modern and antique (though mostly modern) wooden and wicker furniture. All also have flat-screen TVs on the walls and some boast private entrances and fireplaces. In an absolute coup, owners Ben and Bonnie Krupinski snagged Kevin Penner who previously wowed diners at Della Femina for the hotel’s restaurant so, like the American Hotel and c/o Maidstone, evenings here tend to draw a lively crowd. For families and larger groups, there’s also a detached two-bedroom cottage called the Carriage House.

A short drive from Southampton off the Montauk Highway and adjacent to Shinnecock Canal, the historic Canoe Place Inn in Hampton Bays occupies the oldest original hotel site in America.

New Yorkers have been stopping here since the 1690s, when the property first opened. After the American Revolution, what was once a simple guesthouse grew into a refined hotel. But by the 2010s, Canoe Place had transitioned from a coastal resort into a (fabulous) nightclub, with performances by the likes of Billy Joel, P. Diddy and the Ramones.

In 2022, it reopened as a luxury boutique hotel, with 13 guest rooms, seven luxurious suites and five guest cottages (with outdoor showers). Long Island developers Mitchell and Gregg Rechler of Rechler Equity Partners, led the refurbishment, inspired by a “garden by the sea” concept. Some of the original features—seven fireplaces, the vaulted ceilings of the grand ballroom and the dome of the Pavilion—have been preserved. The public and private spaces are comfortable, residential and stylish. The Study, with a fire roaring in its fireplace, is an incredibly cozy place to get some work done or hole up with a book.

From breakfast to dinner, the meals celebrate local bounty with fresh ingredients and there is a great range of offerings curated for different ages and tastes. Breakfast is served in the Bottle Room, a quaint space painted a soft blue with a shelf of vintage kitchenware, including floral Royal Copenhagen plates and vases. Dine on Mediterranean-inspired takes on classic cuisine at the Good Ground Tavern—and don't miss indulging in the sea salt chocolate chip cookies.

The resort also features a pool and spa. Fitting the relaxed vibe, staff here is extremely attentive, warm and welcoming.

Out of all the Hamptons hotels, East Hampton Point most resembles a full-on hotel and amenities include a gym (still quaint though as it’s housed in a former church building), a swimming pool, tennis courts, a playground for children and a topnotch bar and restaurant. It’s a bit north of the main town area, located instead by a pretty marina so guests get a great view of incoming and outgoing boats. Lofty ceilings, fireplaces and large marble bathrooms. Accommodations are divided between suites in a building called the Palmer House and thirteen cottages scattered throughout the property.

In both, the cottages range in size—some are studios, others are duplexes—and many have outdoor decks, Jacuzzis and kitchens. The suites, all of which have their own private entrances, have large marble bathrooms and the nicer ones have high ceilings, private terraces and balconies accessed via staircases. In both, look evoked is English Country, and you’ll find large, four-poster beds, lofty ceilings, fireplaces, Oriental rugs and lots of whites, creams and pastels (popular colors are mint and cerulean). In the Palmer House, common living rooms separate all the bedrooms, so families and groups can choose from an array of possible combinations (granted of course that there’s availability).

A weekend at André Balazs’ Shelter Island outpost is a bit like summer camp – with rosé. There are ping-pong tables, a bocce court, a fire pit and a quirky DVD collection, mountain bikes for toting picnics to out-of-the-way beaches and a steady, almost tropical buzz. On weekends, bikini-clad revelers and European families graze at the lively open-air French restaurant, spilling across the two-lane road onto a sunset-facing stretch of sand called Crescent Beach, appointed with a smattering of bright orange umbrellas and a roped-off swimming area in the glassy sound.

The hotel’s twenty spacious open-plan bedrooms, optic white with kitschy accents (such as beach balls and matching butterfly chairs in cheerful neon), are spare but sufficient for those who plan to spend most of the weekend playing outside. Judging by the tiny bathrooms, which would look almost as appropriate in a college dormitory, you might never suspect that the nonchalant retreat offered seaplane service from Manhattan – or that its summery boutique was stocked with pricey Isabel Marant frocks. The beds, themselves, are perfectly comfortable, and every room has a large private sundeck with reclining chairs and bay views.

Though Sunset Beach has a scene all its own, it is separated from the restaurants and nightlife of the Hamptons (and the wineries of the North Fork) by the Shelter Island ferry. It is a getaway in the most literal sense, the kind of place to kick back with good friends or someone you love, and indulge in summer’s most simple and transportive pleasures.

Built in 1846 when most Sag Harbor residents were whalers, the stately American Hotel is one of the Hamptons’ most historic hotels. The brick building and white columned porch practically serves as a symbol for the town of Sag Harbor. Its downstairs bar has long been a hangout for the region’s famous residents and the restaurant, known for its gargantuan wine list, is one of the hardest to book. The restaurant serves upscale steakhouse fare with an expected Hamptons twist (think littleneck clams and caviar, for example). In warmer months, dining on the front porch makes for excellent people watching. A menu highlight, regardless of season: Maryland blue claw crab cakes.

Restaurant reservations are easier to come by if you’re actually staying in one of the hotel’s eight guest rooms. Each has its own individual décor scheme (one, for instance, features a mounted moose head) but all are large and vaguely Victorian with 19th century furniture and prints, Persian rugs and sitting rooms. Despite the semi-celebrity crowd in the downstairs rooms, the hotel atmosphere and service is not trendy but more of the New England B&B variety.

The Baker House 1650 a pretty stucco inn in East Hampton resembles an English country estate: it’s built in the Elizabethean style and quaint little gardens are scattered throughout the property. Over the years, a number of owners have stepped in—including in 1996, former Maidstone Arms proprietors Gary and Rita Reiswig (who were largely responsible for saving the property from disrepair)—and the building underwent a lot of name changes. Currently it’s run by longtime East Hampton residents Antonella and Bob Rose and the name refers to Thomas Baker, one of the town’s original founders, who purchased the building (which was erected in 1648) in 1650.

The five guest rooms in the main house are all cozy and quaint though each has its own design scheme. The Gardiner, the Maidstone, and the Fithian have pale paisley William Morris wallpaper (in varying colors) while the Hedges and Huntting rooms, located in the older section of the building, have original wooden paneling and exposed ceiling beams. With the exception of the Fithian, all also have wood-burning fireplaces. The best kept secret however lies in the Carriage House located at the back of the property. Two additional rooms, a pool and common area are decorated in a more modern aesthetic done beautifully with Restoration Hardware pieces and elegant artwork. Couples traveling together would feel as though they have rented a private home for the weekend. Unlike most B&Bs, the Baker House also boasts an extensive spa facility, complete with a lap pool, a sauna, a steam shower as well as a hot tub. Open year-round.

Indagare Tip: Pick-up from the nearby Hampton Jitney stop, the East Hampton train satin and the East Hampton airport available; private helicopter services can also be arranged. All guests receive East Hampton Village beach parking passes.

New York City hotelier Sean MacPherson (the talent behind such hits as the Bowery, Ludlow and Marlton hotels) continues his success with the hip Crow’s Nest Inn in the Hamptons. Overlooking Montauk Bay, the hippie-chic property is situated just a five-minute drive from the buzzy surfer town of Montauk. A quiet retreat during the week and a hotspot on the weekends, this charming 14-room inn is perfect for a quintessential Montauk weekend.

The simple accommodations are eclectically appointed, and channel a surfer-chic aesthetic. While the vibe is rustic, guests will find plush mattresses and lovely bathrooms including vibrant tiling and C.O. Bigelow products. Those staying on property are also treated to beach parking passes, complimentary bicycles and a guaranteed table at one the best restaurants in the Hamptons (their own), making staying here a beach weekend made easy.

East Hampton's Maidstone Hotel features bright splashes of color, a myriad of fabrics and textiles, and a breezy, open layout on the ground floor. The chic, 19-room boutique hotel is one of the most charming hotels on the East End.

Each of the Maidstone's rooms is unique in layout and design, but they all share colorful wallpaper (the one in no. 6 has a dramatic red-flower print in the bathroom); lovingly restored antiques, like the mahogany sleigh-bed in No. 19; and Malin + Goetz bath products, flatscreen televisions, DVD players and Playstation 3S. No. 19 right under the roof is romantic, with small windows and a sitting room; No. 11 has a cornflower-blue-and-white color scheme and a four-post bed; No. 6 has a restored Grandfather clock in the bedroom and a clawfoot bathtub. Many of the vibrant fabrics throughout, featuring a huge variety of colorful prints, are mid-century Josef Frank. There are three free-standing cottages in the back garden which are ideal for small families.

The hotel’s restaurant was taken over by Chef David Standridge (who helms the West Village’s healthful Café Clover) in 2017. Guests can enjoy sitting inside the main dining room by the fireplace or outside on the patio and in the garden under hanging lights. The summer-inspired menu includes delicious options like peaches, pesto and vegetable pasta and grilled fish. For those with a sweet tooth, make sure to order the blackberry pie.

Whimsical on-site touches include dog walkers (the hotel is pet-friendly), iPods on loan, and personalized lunch boxes for guests who are planning beach jaunts. Guests can also enjoy complimentary transportation to the beach and towels and chairs. The shops and restaurants of East Hampton are within walking distance of the hotel and guests can use the firetruck-red bicycles to explore the area further.

Open year round and featuring a Jean-Georges–backed restaurant, Topping Rose House is located along the main road in Bridgehampton. The property has 22 accommodations, ranging from king rooms in the main house to luxurious suites in the adjacent contemporary wing, complete with private terraces and gardens. (We recommend staying in the contemporary wing, which is set back from Bridgehampton's busy Main Street and therefore much quieter than the main house.)

In all of the rooms, bed linens are Frette and bath products are from Naturopathica, which are also used in the hotel’s spa and fitness center. The property is fabulously decorated with bright common areas, luxurious fabrics and a sophisticated art collection (it’s curated by Christine Wächter-Campbell, the wife of co-owner Bill Campbell, who owns a gallery in New York City). The sleek, negative-edge pool on property also offers a full lunch menu as well as cocktails while guests lounge.

While not located directly on the beach, the property offers a car service as well as bikes for guests. Topping Rose is also within easy walking distance to Bridgehampton town, home to boutiques and such popular restaurants as Bobby Van’s, Pierre’s and Candy Kitchen. Additionally, there is a recovered barn available for events as well as an adjacent space for larger receptions.