The standard browser's "Browser for File" dialog does not allow you to select more than one file at a time. This is a limitation of the browser and the input type=file control.
The problem is solved in RadUpload for Silverlight where you have control over the file types that are shown and you can select multiple files at once.
I invite you to check our integration demo - RadUpload for Silverlight in an ASP.NET Page
If using Silverlight is not an option for you then you can check this code library
- it allows you to upload a zip file and then un-zip it on the server.
Hope this helps.
the Telerik team
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