Likely the High Power Connector home quick charger for the Model S will be the same as the one for the 2011MY Roadster at the time the S ships.
That being said, they have mentioned that they plan to change the charger they are using right now for 2008MY Roadster: 1) to significantly reduce the cost and 2) to make it less clunky.
They will probably do that for the 2011MY Roadster (my guess... not announced), and that will also work for the Model S. There will likely be adapters to go between the old style and the new.
Additionally the 440v DC-DC quick charge they are touting for the Model S will likely become available for future Roadsters and use the same connection. It is unlikely it will be possible to retrofit on a 2008MY Roadster, from what I hear.