Basic Multiple Image Upload to replace standard image uploader
The best multiple image uploader that I have found is http://drupal.org/project/plupload (example widget is on their website)

Also if you are working with images and are using drupal 7, you may also wish to check out http://drupal.org/project/media - this modules is looking more and more promising, and now has views integration as well. It also works with the above recommended plupload module)