By Priceline bidding standards, your travel dates are a long ways off. Better deals will likely come up as you get closer to those dates. If fact, many of the best deals on PL have come from bids made within a few days of the check-in date. For now, I would suggest being patient. Don't bid more than once every three or four days until you're within a month of check-in, and don't go higher than you've already bid so far. In fact, with so many free rebid zones in Portland for 4* bids, I think I would start even lower -- I don't like winning a room on my first bid. If the idea of not having a room booked until days before check-in makes you uncomfortable, I would also suggest making a fully-cancelable reservation as a backup (actually, you should probably do this whatever your feelings, though I typically don't :) ).