On my current project, we needed to nest Tomcat web apps, similar to:

  http://domain.com/top
  http://domain.com/top/nested

Where “top” and “top/nested” are independent web apps .

Unfortunately, specifying a nested context path in webapps/nested/META-INF/context.xml does not work; neither does physically nesting the web app directories.

What does work is to specify the context for nested in TOMCAT/conf/server.xml. The individual web apps directories remain peers in the webapps directory, as such:

TOMCAT/webapps/nested/
TOMCAT/webapps/top/

and thus may be deployed (and maintained) independently. Problem solved.