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Freezing pickled cucumbers doesn't make sense - they keep for months at room temperature anyway thanks to the brine. After thawing, the texture becomes soft and mushy, and the flavor can change. If the cucumbers are properly sealed in jars, they'll easily last until winter sitting on a shelf in your pantry or cupboard without needing the freezer.
Cool storage is what actually works. Pickled cucumbers keep really well in a basement, cellar, or even in the fridge for several months if the jar is sealed properly. The freezer will definitely ruin the texture - ice will destroy the cucumber's cell structure, and after thawing you'll just get a mushy mess. If you want supplies for the whole winter, better make several jars using different methods or just keep them in the fridge - they'll definitely last until March or April anyway.
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