You can achieve if you use multiple input controls bound to the properties of the action.
<s:form action="doUpload" method="post" enctype="multipart/form-data">
    <s:file name="upload" label="File1"/>
    <s:file name="upload" label="File2"/>
    <s:submit/>
</s:form>
If you are using HTML5 you can add dynamic attribute to Struts <s:file> tag multiple
<s:form action="doUpload" method="post" enctype="multipart/form-data">
    <s:file name="upload" multiple="multiple" />
    <s:submit/>
</s:form>
If you want to prepend the location to the file input control see Remember and Repopulate File Input
Related to HTML5 answer
current/future/HTML5-compliant browsers will always pre-pend the
string: c:\fakepath\ to the filename when getting the file-input's
value On top of that, they will only return the first filename (from a
list of selected files) should the file-input accept multiple files
and the user has selected multiple files.