For the first few years of the anime, there was a video which came out around Christmas featuring Pikachu & friends doing winter stuff...mostly focused around christmas. Here you will find Picutres and Synopsi of Every One

Pikachu's Winter Vacation 1
The Cabin

When Ash, Brock and Misty go into Prof. Oak's lodge for the Christmas Break, they leave the Pokémon in charge of the cabin. Things start going wrong when the Pokémon have their fun. It's up to them to save the Christmas spirit in the house!

Kanga Games

When Pikachu and friends go out for a nice winter stroll, they come across a Kangaskhan and her child. They get the kid Kangaskhan to play with them, but in doing so they end up in danger. Can they get out of it?

Pikachu's Winter Vacation 2000
Winter Games

When in a cabin in Johto, Pikachu and friends decide to play in the cold. But when Chikorita runs off...the group go into an Ice Rink where they play curling using Meowth among other things

Stantler's Little Helpers

Late at night, Pikachu and friends hear something awry. They find out that Santa Claus' steed Stantler is ill. Santa asks them a favour, to goaround and search for a certain berry which would heal Stantler. Can the gang find them, or will Christmas be ruined

Pichu & Pikachu's Winter Vacation 2001
Delibird's Dilemma

Whilst Playing, Totodile accidently shoots a snowball into the air hitting a Delibird. This happens to be Santa's Delibird and all it's presents are thrown about everywhere. Its up to Pikachu & co. to get the Presents back before Christmas is ruined

Snorlax Snowman

When Pikachu & Co. Make some Snowmen in the Snow, Totodile makes a 'Snow'lax. After going to sleep, the 'Snow' comes to life and ask Pikachu & Co. to help it go back to it's group on 'Snow'laxes. Can Pikachu help 'Snow'lax?

We The Pichu Brothers

When the Pichu Brothers fight, they knock out eachother and one of them slides on a skateboard out of town with Wooper chasing him. His brother and his friends have to look for him. But When the Missing Pichu ends up high above the rest, things start to go wrong. Can the Pichu Brothers be Re-united

 
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