Here is a possible solution. If the Windows machine is Windows 98 or better, you could easily use Apache as a web server, and create the application as a CGI application. If there will be multiple users on a network ever, this is probably the easiest solution. Daring a stoning on this site, but PHP is another possibility. A binary version is available from php.net and is easy to install.
Going with VB would lead to .dll hell. C/C++ would likely take longer to code. A Perl/Python/Tcl and Tk solution would also likely take longer than a CGI based solution.