Located at the top of Main Street, this 12-room B&B is in the thick of Southampton's affluent action (Saks Fifth Avenue is next door) but is also an unstuffy retreat from it. The guest rooms ramble around the original 18th-century house, a 19th-century building, and a 20th-century addition with a contemporary annex. Rooms are individually decorated with floral bedspreads, Oriental carpets, and antiques culled from innkeeper Lorraine Ralph's antiques shop down the road. Exposed timbers and a canopy bed lend a rustic atmosphere to Room Two in the original house, while Room B, in the more modern annex, is airier and set up with a king-size bed and a flat-screen television. There's no on-site restaurant, although there are many within walking distance, and self-catering types can book one of the three two-bedroom cottages in the back garden, which have kitchens, spacious living rooms, and porches.

Dating back to 1846, this eight-room hotel near the water in Sag Harbor maintains a classic 19th-century feel. Each of the spacious guest rooms has a unique look—one is very Victorian, while another is equipped with fireplaces and a mounted moose head. All have antique furnishings, sitting areas, and double Jacuzzi bathtubs; not a single one has a television. Unlike its glam neighbors East Hampton and Southampton, New England–style Sag Harbor remains sleepy, even in the heady summer months, and its whaling-village history is still evident. Even so, there are plenty of browse-worthy shops, art galleries, and restaurants: Harbor-side Beacon serves New American fare (www.beaconsagharbor.com), Grappa wine bar is a good bet for tapas (www.grappawinebar.com), and the American Hotel itself is a popular place for dinner and drinks.

Staying at the Atlantic is like having a Hamptons share house, just without the commitment and the twentysomething housemates. The motel's 62 rooms aren't much to look at: The cheesy fixtures would be at home in a college dorm, but at least the formerly downtrodden bathrooms have been spruced up. The draw is a party atmosphere—which is cranked up on holiday weekends, when lounge-y music is piped in for poolside barbecues. (Note that a 24-hour gas station across the street is well positioned for late-night beer runs.) Plus there's the cachet of being within a few miles of Southampton's downtown and, of course, of having a spot by the pool in the eternal Hamptons sun.

East Hampton's Arts and Crafts–style Baker House is the most luxurious inn on the East End—and the most expensive. Rates soar to $800 per night on summer weekends, but you do get what you pay for. The spacious Gardiner Suite—our favorite of the five rooms—has a wood-burning fireplace, a two-person spa tub, and mullioned windows overlooking the walled English gardens and the hotel's elegant infinity-edged pool. The divine Maidstone Room counters with a sleigh bed and views of East Hampton's village green. Massages, facials, and body treatments are available in the guests-only spa (there's also an indoor lap pool, sauna, and steam showers), and guests receive coveted parking passes for East Hampton's nearby strands, such as Main Beach and Georgica. The well-stocked library and honor bar contribute to the sense of staying at a friend's glorious country home—that is, a well-connected friend who can help you secure reservations for the top tables in town and tickets to the most exclusive events.

This 28-room 1950s beachfront motel is a long way (both geographically and psychologically) from the New England-y B&B-style inns of the Hamptons proper, which is exactly how the devoted regulars like it. This is definitely a no-frills, un-Hamptons experience: There are no high-thread-count sheets, Bulgari soaps, or any shampoo at all, for that matter—just simple motel accommodations. Some rooms have kitchenettes, which is good since there's no on-site restaurant, and the village of Montauk is a mile to the east. What is right out the door is the area's best surf break, Ditch Plains, meaning that even if the hotel's in crowd of photographers and barefoot media types can't swim in the water, the cool factor remains high.

East Hampton Point gets high marks for its family-friendliness, resortlike amenities, and proximity to busy Three Mile Harbor. Located in Springs (a locals' neighborhood five minutes by car from East Hampton, where Jackson Pollock once painted), East Hampton Point consists of seven suites and 13 cottages. The spare suites are tastefully decorated in muted blues with dark-wood furniture and have plasma-screen televisions, large bathrooms, and private entrances. Book an adjacent sitting room for more space, or to link suites. (Suite 6 also has a private second-floor terrace.) The cottages are homier, with full kitchens and private patios protected by privet hedges. For entertainment, there's a pool, tennis court, playground, and the marina—all rarities in the Hamptons, given the prohibitive cost of real estate. Chef Craig Attwood serves a New American menu at the on-site restaurant, but if you plan on dining out, ask the front desk to make a reservation—the hotel proprietors are also co-owners of East Hampton hot spots Citta Nuova and Wei Fun.

While not as elegant as Baker House 1650 (and with smaller rooms), the Hedges Inn still has a dynamite location, plenty of charm, and lower rates than its rarefied neighbor (topping out at $650 per night in-season). The Hedges was also refreshed with a multimillion-dollar renovation before reopening in summer 2008. Beadboard wainscoting, beachy pastel hues, antique reproduction furniture, and flat-screen TVs outfit the 12 rooms, which also have marble-clad bathrooms. The comfortable living room is a good place to watch movies and munch on popcorn; bring your own DVD, and the innkeeper will pop the corn. There's no restaurant or pool, but East Hampton's restaurants are a ten-minute walk away, and guests receive parking permits to nearby East Hampton Village beaches (along with beach chairs and towels) as well as passes to the East Hampton Gym.

Despite slightly rickety staircases and a bit of peeling paint here and there, the picturesque 300-year-old Huntting Inn, encircled by a picket fence and shaded by a majestic elm, is one of the best hotels in the Hamptons. The look of the interior is French country, with bright quilts and (in some rooms) floral wallpaper, making it the perfect place to take a break from the area's seaside theme. This mansion also houses a tony branch of The Palm steak-house chain, an East End institution since 1979 (631-324-0411; www.thepalm.com). Everyone from beach-house owners to celebs—including Robert De Niro, Billy Joel, and Calvin Klein—to starstruck tourists pack in here, clamoring for seats on the porch and enjoying large portions of dry-aged steaks, jumbo lobsters, and Italian-leaning classics such as linguine with red or white clam sauce.