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Windermere is set in the Lake District, which is one of the rainiest areas in the United Kingdom. The best weather is usually during June, July, and August, which is when most of the festivals take place. But summertime is also the “high season,” when the area is flooded with visitors. So expect large crowds and limited parking. Or, consider bringing rain gear and traveling during the spring or fall, when rates drop significantly. During the winter you may have the area to yourself, but many of the attractions close due to snow.
Whatever time of year you visit The Lakes you should take waterproof gear and walking boots. It is true that the towns can be very crowded in summer but a few minutes outside the town and you can be in beautiful countryside with only other walkers to meet now and then. Winter can be magical if you are lucky enough to get snow. Autumn and spring have their own beauty too and even if it does rain this adds its own dimension. Do remember that beautiful as it is the Lake District claims casualties every year who forget that the weather can change in moments. Take sensible precautions if walking in the hills at all times of year.