Pandas Dataframe: how to add column with number of occurrences in other column

groupby on 'col1' and then apply transform on Col2 to return a Series with its index aligned to the original df so you can add it as a column:

In [3]:
df['Occur'] = df.groupby('Col1')['Col2'].transform(pd.Series.value_counts)
df

Out[3]:
    Col1       Col2 Occur
0   test  Something     2
1  test2  Something     2
2  test3  Something     1
3   test  Something     2
4  test2  Something     2
5  test5  Something     1

You can also use GroupBy + transform with size:

df['Occur'] = df.groupby('Col1')['Col1'].transform('size')

print(df)

    Col1       Col2  Occur
0   test  Something      2
1  test2  Something      2
2  test3  Something      1
3   test  Something      2
4  test2  Something      2
5  test5  Something      1