A few additional questions to help with ideas (if you don't mind):
1) Is airfare paid in cash or do you also plan on using miles?
2) Is there a desire to stick with cold weather (i.e. your in the NE) or go to a more warmer climate
3) Are you looking to lounge around or sight see? Any particular interests? Cultural, historical, etc.
4) Is there any specific limitation geographically/logistically (i.e. flight time vs. easy to get to)
You certainly have plenty of points for nights just about anywhere, and there are aspirational properties just about everywhere (if you consider high end hotels in expensive cities and expensive resorts in the middle of nowhere one and the same).