I'm doing something similar. If I can get WH-DT cheap, it's my first choice. But it's also likely to be the most expensive. CC-CH is my second choice due to being cheaper than WH-DT, but possibly just a little more than DC-WP. However I think I'm most likely to get DC-WP based on cheap over touristy convenience. And having stayed there once before. So in order to get extra bids where I expect to land (DC-WP or CC-CH), I'm bidding them in order of expected price. That way, after doing all the standard free rebids, I can get one more when WH-DT is added to CC-CH and two when WH-DT and CC-CH are added to DP-WP. Since I've already bid them higher, and would be happy to stay there anyhow, I don't expect them to be accepted when bidding my lower areas. Here's how I've done it using only 4*: WH-DT @ $125 Add AW @ $130 Add Beth @ $135 Add CC @ $140 Add DC-NE @ $145 Add GN @ $150 Add MV @ $155 Add SS @ $160 (none accepted) CC-CH @ $100 Add AW @ $105 Add Beth @ $110 Add CC @ $115 Add DC-NE @ $120 Add GN @ $125 Add MV @ $130 Add SS @ $135 Add WH-DT @ $140 (none accepted) DC-WP @$50 Add AW @ $60 Add Beth @ $70 Add CC @ $80 Add DC-NE @ $85 Add GN @ $90 Add MV @ $95 Add SS @ $100 Add CC-CH @ $105 Add WH-DT @ $110 (none accepted) So as you can see, I had 8 and 9 rebids with this strategy. I've got a few weeks before my trip and have a Saturday night first night, so I'll start revising the bids as I get closer. Right now I'm hoping to get lucky on the cheap side.