16:6a Perhaps I will stay with you awhile, or even spend the winter,

I may stay with you (plur.) for a while, and I may even stay with you through the winter.
-or-
If it is possible I will stay with you for some time, perhaps until the cold season is finished.

16:6b so that you can help me on my journey, wherever I go.

Then you (plur.) can support me on my way, whichever way I go.
-or-
Then you can give me the things I need for my next trip, wherever I go next.

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