Are you trying to randomize the date of departure with the constraint that it be between January 3 and January 29? Or, are you asking how to insert it into another table? If you are trying to randomize:DATEADD( day, 1 + 26*RAND(checksum(NEWID())),'1/2/2012')
If you are trying to update a column, the code would be something like this: UPDATE tbl SET DepartureDate = DATEADD( day, 1 + (LengthofStay-1)*RAND(checksum(NEWID())),ArrivalDate)