You can't do all of that in one day. Israeli cars can't go into Jericho and Bethlehem. It is about a 90 minute drive to Massada and you require about 2 hours to tour it.
Abraham Tours runs a Dead Sea, Masada, Ein Gedi tour every Saturday. It is a transportation only tour, but there are audioguides at Massada.
http://abrahamtours.com/theme/israel-tours/