I have now been out to the Hamptons on two separate occasions and have had some great times and met some really great people. Before I arrived in the States, I booked into two different Hamptons share houses.
A Hamptons Share house can vary with what is offered and how it works, but typically, the House is shared over the Summer which comprises 16 weekends, and people often purchase a quarter share (4 weekends) or a half share (8 weekends). I purchased a quarter share in a house on Millstone Road in Bridgehampton and 2 weekends in a house arond the corner on Noyac Path. The second house (a bit different to most houses) allows for any number of weekends to be booked.
I spent my first weekend on Millstone Road and my second (this past weekend) on Noyac Path. The two houses could not be more different, and each has its pros and cons. People that stay in the house on Millstone Road are screened to ensure that they fit with the remainder of the house, which tends to be fairly cool, outgoing (dare I say) good looking people, whereas the other house allows all sorts of people. To be somewhat politically incorrect, the Noyac Path house is referred to by the Millstone House people as allowing "Freaks and Geeks" to stay there. And ther are not entirely wrong. Having said that, I did meet some nice people and even some good business contacts there. I also spent most of my time last weekend hanging out with the people from the cooler house even though I was staying at the "Freaks and Geeks" house!
On the positive side for the Noyac Path house, they have maids that cook, clean and make your bed and there's loads of food and amenities that you take for granted like hand towels and hand soap in the bathrooms and lots of lilos for the pool. The Millstone house has none of that, which tends to make you feel like you are staying in a dorm.
Both houses organise outings to the local night spots of THEIR choice, as they get kickbacks from certain places for bringing a lot of people to the club. If you want to go somewhere else, you are likely to get loads of discouragement from the house organisers. I even heard a story about some people that booked a cab to go to an alternate nightspot, and then the house organisers turned around and cancelled that cab! Obviously the house organisers don't go to the trouble of organising a share house for the love of it, they need to make money out of it, but not at the expense of free will!!!
Not having been to a club in the city yet, I can't compare the Hamptons experience to the NY experience of clubbing, but to my mind, as is the case for many things in NY, night clubs are all about creating products that have differing levels of eliteness in order to extract more money from the punters. Most night clubs offer bottle service, which means, if you want to sit at a table you need to purchase bottles of alcohol which can tend to cost upwards of $300 each. On my first weekend, there was a guy that dropped about $1500!
Fortunately, being of the female persuasion, it is entirely possible to get away without spending any money on drinks, but one has to be fairly careful that the acceptance of drinks does not imply another type of obligation... True, this is a universal concern, but New Yorkers tends to be that much more aggressive and crass when it comes to these matters. Further elaboration is probably not suitable for this audience :)
My most recent Saturday night in the Hamptons involved a visit to a club called Pink Elephant, check out the link for photos and a description to get an idea. Outside are poolside-type cabanas surrounded by sand that you have to purchase bottle service for. You need an orange bracelet to go inside and outside, or a yellow bracelet just for outside. I was *lucky* enough to score an orange bracelet. It was a fun night, if not a little over the top!