As a newbie to the hotel points game, I am trying to figure out whether it makes more sense to spend dollars or points for an upcoming 3 night stay in Maui in early November. It's a mileage run to maintain my elite airline status, and I was hoping not to spend a lot for the room. But I like nice hotels, so that may be unavoidable. A room at the Hyatt, Westin, or Marriott, including parking and resort fee, will run about $280-295 per night. The Westin is available for 12,000 points per night plus $25 resort fee which includes parking. Cash and Points is not available (except for the more expensive Westin villas, which cost 8000 points plus $150, and maybe other fees also). For my usual airline mileage redemptions, Starpoints are worth at least 2.5 cents to me -- but I do have an accumulation of air miles, so I don't need the points in the near future. Using points for the 3 nights would deplete my SPG account. I have no Hyatt points, but I do have a suite upgrade certificate. (I've already committed my free Hyatt nights to Paris.) One night at the Marriott is 35,000 points plus $56 resort fee and parking. That doesn't seem like a good deal. Also, I don't have enough points for all three nights and I wasn't planning to apply for the Marriott card until a bigger bonus comes along again. (And I've applied for the Hyatt and Fairmont cards within the last month.) My first choice would to use my two free Fairmont nights in Maui, and pay dollars for the third night, but since I just applied for the card, the stars would have to align just right for that to work out. So Plan B is either to pay $900 for the Hyatt in an upgrade to a suite, or to use 36,000 points for the Westin. I think perhaps the Hyatt is the better deal, if I can use the suite certificate on the AAA rate. Or maybe I should forget the points and the upgrade and use Pricelline, which I have never done before. Any thoughts from the experts? I know that I am WAY overthinking this. I know intuitively when to use miles or money for a plane ticket, but it will take me awhile to get used to the different values of hotel points.