This VBScript will do it. Create a shortcut to it with the argument being the name of the playlist you want to playlist. (i.e. the "Target" will be 'some folder pathitunes
playplaylist.vbs" playlistname') You'll have to use a scheduling app (e.g. the built-in "Scheduled Tasks" ) to run it at the time you want.
Right-click and save as this link:
http://home.comcast.net/~teridon73/itunesscripts/itunesplayplaylist.vbs
Or copy and paste the code below into a text file and name it with a ".vbs" extension
Option Explicit
Dim iTunes ' iTunes.Application object used to access the iTunes application.
Dim playlists
Dim playlistName
Dim playlist
Dim arglist
Dim args
Dim arg
Dim i
On Error Resume Next
Set args = WScript.Arguments
Set arglist = wscript.arguments
If arglist.Count = 0 Then
wscript.echo "You must provide a playlist name"
wscript.quit
End If
playlistName = arglist.item(0)
Set iTunes = CreateObject("iTunes.Application.1")
Set playlists = iTunes.LibrarySource.Playlists
Set playlist = playlists.ItemByName(playlistName)
If Len(playlist.Name) = 0 Then
wscript.echo "No playlist found by name " & playlistName
wscript.quit
End If
iTunes.BrowserWindow.SelectedPlaylist = playlist
iTunes.Stop
iTunes.Play