Ooooh, where to start!
We own at the Hilton Club, which is linked to the Hilton Hotel at Avenue of Americas. It's about 10 minutes walk to Times Square. The hotel itself is not mega luxurious, but club level is fabulous - the lounge is really elegant and there are absolutely incredible floor-to-ceiling windows looking out over the city and Central Park. They serve breakfast, afternoon snacks and hors d'oeuvre in the evening with a cash bar. You can usually get a one bedroom club level suite here for about the same (or less) as a regular room in one of the more up scale and renowned hotels.
We also enjoy the Ritz-Carlton at Central Park. It's right near Fifth Avenue but a little further from Times Square. The room rates are pretty $$$ but the staff are absolutely awesome and the service really is incredible - you get champagne and hors d'ouvres while checking-in and the staff member takes you to your room personally. IMO it's worth the premium to get a park view room.
The Mandarin-Oriental is great but it's harder to get good deals than other places. You can get rooms overlooking the Hudson and the lobby is really high-up with some awesome vistas. We always have to make a reservation at the Asiate restaurant because the food is incredible!
I think that the Plaza is a little overrated, but having said that we haven't been there since their huge renovation a couple years ago so it might be a million times better now. Location wise, it's really central - though it's a little further from Times Square. Four Seasons has always been great and both times we stayed there we got upgraded, despite not being "frequent" guests or anything. It's got a great spa and fitness centre too...
Personally I'd recommend the Hilton club level the most. It is a bit generic being a Hilton, but the location is awesome and the value-for-money is definitely top-notch compared to other similar hotels. Don't forget you can get VA flying club miles too! There's another Hilton in Times Square itself, but we've never experienced that one. Might be worth a look if that's where you want to be, but definitely check out the club level prices because they tend to be pretty good value for what you get.
