Trying to sort through the various TV Specials and OVA's for Pocket Monsters can be quite a difficult task.  TV-Tokyo often advertises the airing of Pocket Monsters movies and Mini-Movies as specials, making many people think that "Oh, Special #5 is the third movie."  Here's what I understand the various specials to be, and hopefully I can clear up some confusion: 1998/1999/2000/2001

Japanese Title:  "Pikachuu no Fuyuyasumi 2000" (OVA)

(Pikachu's Winter Vacation 2000)

Amerian Title:  "Pikachu's Winter Vacation 2"
Air Date:  ???
VHS/DVD:  December 22nd, 1999 (Japan)
December 2000 (US)

This is the second in the "Pikachu no Fuyuyasumi" series in Japan.  Like the first one, it was dubbed by 4Kids, but it was also marketed as poorly as the first one.  The videos were sold only in Wal-Marts, so they're practically impossible to find.  Unlike the previous special, I've actually seen this one, and I can tell you that these Winter Vacation stories are sickingly cute.  The dub is well-done, though--the music is kept as-is, without 4Kids' usual "filler music" used throughout the television series. 

The first ten-minute short, "Ko'ori de Asobou" ("Enjoy the Ice"--"Winter Games" in the dub) shows what happens when the pokemon are left alone during the wintertime.  Satoshi-tachi leave the cabin they're staying in to go shopping, and the pokemon are left behind until they return.  The pokemon breathe on a window and press their faces against the glass, making little designs on the fog.  Everyone except Chikorita, who's more or less pushed to the side.  After a little while, everyone goes outside where they discover icicles hanging low to the ground.  The pokemon discover that they can make music with the various icicles, and so a nice little tune is played out, again without Chikorita.  The jealous grass pokemon uses a Leaf Cutter (Razor Leaf) to cut down the icicles, ruining everyone's fun.  The other pokemon start to chase Chikorita until they reach an iced-over pond, where everyone forgets their anger and starts playing around on the ice.  Nyasu appears and decides to show everyone how a pro ice-skater skates, but as soon as its foot hits the ice the pokemon goes flying straight into a tree.  The other pokemon laugh, so Nyasu pushes Fushigidane into a tree.  Angered, the grass pokemon picks Nyasu up with its vines and spins the cat pokemon like a top, sending it blasting off.  The pokemon continue playing until sundown, when Satoshi-tachi arrive to pick their pokemon up.

The second short, "KURISUMASU no Yoru ("The Night of Christmas," or "Stantler's Little Helpers" in the dub), brings us to Satoshi-tachi's cabin on Christmas Eve.  After everyone goes to bed, all the pokemon come out of their Monster Balls and look at a beautiful Christmas tree that's placed outside.  As the pokemon gather around, the weight of all them pressed against the window causes it to fall through, sending all the pokemon falling into the snow.  They get up and happily run around for a bit until they encounter Santa Claus and his Odoshishi.  The Odoshishi is sick, and so Santa can't deliver presents!  He tells the pokemon that he needs a bunch of special berries, so the pokemon all agree to search for them.  After a little bit of searching without success, Pikachu gets an idea--the pokemon all return to the Christmas tree outside Satoshi-tachi's cabin.  Chikorita uses its razor leaf to cut down the star that's on the very top, and then Pikachu puts it on top of its head. Using its electric powers, Pikachu is able to make the star light up, providing illumination for the searching pokemon.  The pokemon resume their search and happen upon a cliff, and at the top of that cliff is a bunch of the berries!  Pikachu climbs the cliff, with the other pokemon cheering it on, until it reaches the berries!  The pokemon triumphantly deliver the berries to Santa and he gives them to Odoshishi.  Odoshishi gets better, and now Santa can deliver presents to everyone!  Satoshi-tachi wake up the next morning and find a bunch of presents for them while the pokemon rejoice in their successes.

1998/1999/2000/2001