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Every year around this time of year, I'm in a bigger retro mood than usual but I specifically go for games with winter themes or settings:

Lemmings Xmas edition
Cannon Fodder
Commandos
Jazz Jackrabbit (Xmas edition)
Spud!
etc.

But I'd like some recommendations for other games that have plenty of snow or a Holiday theme to it to get some variation this year. Thanks!
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Icewind Dale series, of course.
Ski or Die! (Sno' way bro!)
Lode Runner: The Legend Returns (Has snow levels and the monks are dressed in red. :P)
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Catshade: Icewind Dale series, of course.
I was just about to recommend it. :)
Also:

Star Wars: Yoda Stories has Hoth snow levels.
Snow Bros. (Console/Arcade) (Sort of like Bubble Bobble)
UT2004 has a number of Christmas themed mods.
Max Payne.
Warcraft III: The Frozen Throne - Plenty of snow
Secret of Mana (Super NES) - You meet Santa!

Edit: Also, Snow Fight
If you actually have a Sega Saturn there's Christmas NiGHTS into Dreams.
Sam and Max: Season 2: Ice Station Santa
Post edited November 23, 2010 by EndlessKnight
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Catshade: Icewind Dale series, of course.
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gyokzoli: I was just about to recommend it. :)
Already played those to the end but I might have another go but ideally, I'd like some fresh ones to play.

Also, don't be afraid to recommend several - I've played loads more than I listed so the obvious ones will probably already have been done :p
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EndlessKnight: Warcraft III: The Frozen Throne - Plenty of snow
Secret of Mana (Super NES) - You meet Santa!

Edit: Also, Snow Fight
If you actually have a Sega Saturn there's Christmas NiGHTS into Dreams.
Sam and Max: Season 2: Ice Station Santa
I might try to get my Sega Saturn emulator to work with that.

And yeah! Sam & Max Season 2 is a good one - I own all episodes of all seasons yet only played the first three of the first season.
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Mentalepsy: Max Payne.
I only completed it last year for the fourth time so it would be a bit too soon - brilliant game though. I might give MP2 a go this year.
Post edited November 23, 2010 by Red_Avatar
Flatout has winter courses.
The classic windows downhill skiing game, SkiFree. (Basically WinSki from Windows Entertainment Pack)
Post edited November 23, 2010 by EndlessKnight
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Red_Avatar: but ideally, I'd like some fresh ones to play.
How about Snowcat Simulator? Can't get fresher than those. :P

Or if you like survival horror games with deadly snow and supernatural occurences, there are Cursed Mountain and Cryostasis.

Or if you have a Wii/PSP/PS2 (and preferably a child), get Silent Hill: Shattered Memories. Heck, just rent it if you don't want to buy it (it's a short game), it's a darn good winter game!
Post edited November 23, 2010 by Catshade
Age of Wonders 1 and 2 has winter levels
Neverwinter Nights - Shadows of Undrentide has a winter setting I think
Syberia 2
Club Penguin: Elite Penguin Force: Herbert's Revenge
There's a party in one of the missions in Hitman Blood Money, where you can kill a drunken santa to get his clothes. Some guards also wear santa hats. : P

Edit: If you want games with snow, why you don't play snowboarding games? But I don't know if you like this type of game.
Post edited November 23, 2010 by Drelmanes