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You can apply stain over peeling stain, but it’s not a good idea. Your old stain will get in the way of your new stain bonding to the wood, so you’re likely going to see the same issue again shortly after application. Your best option is to sand off the old stain and clean the surface thoroughly before applying new stain.

If possible, it is beneficial to paint both sides of your fence to protect the fence more completely from the elements. Painting both sides of your fence will create a more consistent appearance as well. However, the time and cost involved in painting both sides of the fence may cause people to paint only the side they see.

While power washing isn't a requirement before you stain a fence, it can make the job much easier and faster while reducing manual labor requirements. The stain will not work if the wood is full of dirt and dust, so power washing, sometimes called pressure washing, is a fast and effective way to prepare the wood for staining. Remember that you need to stain or repaint relatively soon after the wood has dried so that there isn’t time for dust and dirt to build up again. 

To prevent a fence from becoming dirty, hose it down weekly and after every time you mow the lawn. This will prevent algae from being able to feed on grass clippings. You should also wash your fence once per season and trim plants so they don’t touch it. As a precautionary measure, you can treat your fence with a coating of a mold prevention product.