Weymouth isn't too bad, if you want somewhere cheap I'd recommend Bournemouth as it's got more of a variety hotel-wise, 5 times the amount of clubs and bars than Weymouth, a beautiful beach. From experience myself I've found most places in Bournemouth stay open later and several clubs do drinks for £1 (although New Years will be different I can imagine). Weymouth is still okay but you'll be very limited to clubs, the hotels and B&B's are okay but I can't guarantee they're any good as I live in Weymouth, only stayed in Bournemouth for all nighters. Hope you guys can find some good deals :)
If you do decide on Weymouth, it depends on your budget. For "posh B&B", I would look at B+B on the esplanade, you are right in the heart of things, and not far to walk (or stagger) when you have had enough.
For pubs, don't be fooled by the pay parties, they are always pretty empty, most people prefer to stick to the pubs, which open until about 4AM or so. If you prefer to watch the fancy dress, get to one of the Wetherspoons early and grab a seat :-)
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