Originally Posted by
WillTravel
The main risk is that you won't get the same place. If you don't care whether you have the same place or not, then bid however you like. It is theoretically possible that a hotel could have one room at a cheap price, but not two, but that would mean that you would indeed probably end up at two separate places with two bids.
Exactly. If you want two rooms in the same hotel, always book at the same time requesting two rooms. Sure there is a chance one room would have been cheaper but if you really want two rooms, two at almost any priceline rate (after doing your homework) is still going to be way cheaper than conventional rates.