The Hamptons are completely overrated. The weather there is very cold and damp. The beach isn't even that nice either. Whenever I've driven down there, I always knew I was getting close because the cold damp air would seep into the car. And it was the same when I would take the train there.
Basically, it's all about city people going there on weekends and pretending to be "countrified." There's also the bragging factor.
A long time ago, I did a share house there. The way it works is that the house is rented to different people on different weekends. So this one weekend, everyone came. There were people actually sleeping in the garage.