I am using Visual Studio 2015 and Web Essentials extension and I modified the solution level "compilerconfig.json" file to map the multiple input-output files and it works for perfectly for my by compiling all of the input less files into css output files.

[
{
"outputFile": "css/styles.css",
"inputFile": "css/styles.less"
},
{
"outputFile": "multiselect-dropdown-lib/MultiselectDropdownStyle.css",
"inputFile": "multiselect-dropdown-lib/MultiselectDropdownStyle.less"
}
]

I re-read your question and I think you are looking for compiling all LESS files into a single CSS file. If that is the case, then my soloution is slightly differnt. It compiles all LESS files into corresponding CSS files.
586, column 9: 585 .spanX (@index) when (@index > 0) { 586 (~".span@{index}") { 587 .span(@index);- user2572639