Sorting out your file names in Windows can feel like a pain, but it’s a necessary one – having hundreds of photo files from three different holidays with the horrible file names, such as ‘DSCF0012’, doesn't help you find the picture you're after.
Renaming files one at a time in Windows is far too laborious. There’s a much simpler way to rename every file in a folder all in one go in Windows.
First, copy and paste all of your photos from one event into one folder and give it a suitable name (eg ‘Italy holiday 2015’). Keep the files in either chronological order or ordered by 'date modified'. Both will have much the same effect with digital photos taken from the same event - they'll appear in the order taken. Make sure you're happy with the order they appear in before renaming them in the next step.
Next, select all the files in the folder by pressing Ctrl + A. Right-click on the first file and select Rename. Choose a name for all of the files (eg ‘Italy 2015’).
Windows will name them automatically as ‘Italy 2015 (01)’, ‘Italy 2015 (02)’, and so on.