The best deals in Downtown Portland are generally at the 3* level. I think this would be particularly true during the holidays because the most frequently won 3* hotels -- the Hilton and the Marriott Downtown Waterfront -- are business-oriented hotels. The only risk, it appears, would be getting the Hotel Fifty (formerly the Four Points). If you're willing to tolerate this risk, I would try the following bidding strategy to start: You have two rebid zones for a 3* bid: Beaverton-Hillsboro and NW Portland. Start a new bid of $45 for 3* DT Portland Add rebid zone #1 and bid $48 Exit this bid and start a new bid of $50 for 3* DT Portland + rebid zone #2 Add rebid zone #1 and bid $52 If you really want a 4*, you can split your bids as Colfax suggested, but keep in mind that there is a reasonable chance that your split bids will be accepted at two different hotels. Also, the lowest rates for the Benson are in the middle of your stay -- the 23rd-25th -- so I'm not sure how effective splitting would be if you want the Benson. I think it's best to just be patient; most of the 4* wins reported lately have been within about a week of check-in. I would recommend that you make a fully cancellable backup, then bid every 2-3 days, each time starting at $55 and working your way up to about $80-85. If, 5-6 days before check-in, you're unsuccessful, you can decide if you want to split your bid, try for a 3*, or keep trying the single 4* bid and stay at your backup hotel if it ultimately fails.