We need a little more info. How many people? How many points are available? Any temperature preferences (warm or cold)? I find that the more expensive rooms are usually more available. For example, you could probably get a room at Kings Land for 2 weeks in January. 2 consecutive weeks will be tougher. I'm not sure what a "great" vacation would be for you. Maybe Vegas could be fun too. It doesn't get that cold in the winter there but it does get a bit chilly. My advice would be to focus on the main areas that Hilton occupies: Hawaii, Vegas, and Florida. That would make it easier to get 2 weeks this far out. If you start looking at 9 months out, it's easier to find longer stretches. I stayed at Kings Land and it's nice. Nobody ever said Hawaii sucked and it's always warm.