The Hamptons

If you haven't booked a hotel reservation for your Hamptons vacation weeks or even months ahead (especially around Memorial Day, July 4th, and Labor Day), finding a hotel room can be daunting. Finding an inexpensive hotel room is even harder: Summer weekend rates at the New England–style inns of Southampton, Sag Harbor, and East Hampton routinely top $500 a night. You'll find the cheapest rates at the funky motels lining busy Route 27 (often within easy driving distance of the most popular villages and beaches). But even there, weekend rates of $350 or more are common; midweek rates can ring in under $250. Note that for weekends from July through Labor Day, three-night minimums have become standard at many hotels. Sleepy Shelter Island, with its B&Bs, galleries, and vast nature preserve, is the best place in the Hamptons for a quiet retreat—with the notable exception of the revved-up Sunset Beach. In anything-goes Montauk, you'll find family-friendly beachside hotel rooms overlooking the dunes and retro roadside motels where the creature comforts haven't been updated in decades. If you're planning to stay for a week or more, try renting accommodations: Again, there are no great bargains to be found, but if you wait until late June—when property owners who haven't yet rented out their houses (or whose rentals have fallen through) start panicking—you may just get a hefty discount. The best trick, however, is to become fast friends with a wealthy Hamptonite who loves houseguests: A weekend visit at a far-flung estate will cost you only some witty repartee and the price of a hostess gift (think orchids or a scented candle).