I used BetterBidding’s Priceline and Hotwire Calendar of Wins for my vacation period and reviewed the Kaanapali resort bids made as far back as April for stays throughout the summer. My research led me to expect to get the Sheraton in the $175-$190 range or the Hyatt in the $150-$155 range. I ended up winning the Hyatt at $160 and here is the process I used: Round 1: 1st Bid (Kaanapli-Lahaina): $135 (Priceline countered with asking me to bid $160) * 2nd Bid (+Kihei) : $145 Rejected 3rd Bid (+Kahului): $150 Rejected Round 2: 1st Bid (Kaanapli-Lahaina): $145 (Priceline countered with asking me to bid $175) ** 2nd Bid (+Kihei) : $150 Rejected 3rd Bid (+Kahului): $155 Rejected Round 3: 1st Bid (Kaanapli-Lahaina): $135 (Priceline countered with asking me to bid $160) 2nd Bid (+Kihei) : $155 Rejected 3rd Bid (+Kahului): $160 Winning Bid * From my previous experiences with Priceline (I have bid on Priceline hundreds of time – I used to do a lot of consulting work travel) if they offer you a rebid at a higher price, you can usually win by increasing your previous bid by about 1/3 of the spread between your previous bid and what they are offering you. Of course you can’t enter that directly, you have to add an area or change a date. However, as you can see in this case, and this is the first time ever I have encountered this, they stuck to their guns at $160. ** This counter-bid surprised, offended, and scared me. Had I lost my opportunity to win at $160 or were they gaming me given my higher starting bid of $145? I decided to keep my nerve and start over again at $135 and see what happens. They came back with $160 again and so I resumed my $5 increments from the first day and we reached an agreement at $160. Thanks BetterBidding!