Don’t worry too much about getting a hotel near Central Park.. you probably won’t be able to see the park from your room, and the park is really a short subway ride from pretty much anywhere. Plan on getting a MetroPass, and take the subway as often as you can… the bus takes too long and taxis can be… an adventure.
In terms of quirky hotels, I do remember reading about the Library Hotel, never been (I live 20 mins away, no point in staying the night for me) http://www.libraryhotel.com/ I don’t know where it is, only that it involves rooms organized by books.
If you’ve never been before, consider mixing a few “tourist” destinations with a few fun and funky ones: going to the top of the Empire State building, visting some museums, maybe even a double decker bus tour (my mom wants to do that so badly, I don’t know why… she lives 20 mins away too). If the weather was nicer, I’d suggest the Highline, but it will be open anyway and is a really neat park in a really neat neighborhood (very close to the Chelsea Market).
OH! Brooklyn Bowl! Do you like bowling? That place is a lot of fun. Literally right next door to the Brooklyn Brewery, and there’s some neat thrift shops and sometimes craft/ food fairs in that neighborhood. It’s literally a subway ride away, not too far to make both a date night. You can always get a taxi back if you like (even though I’m not cray about them, save some money for taxi rides… they’re good to have when you need them)
Speaking of fairs, if you go in November, give yourselves some time to walk around the holiday craft markets. There are a few around, I usually wind up at the one near Union Square? I forget.
BTW, on the subject of holidays… the city will have more people than usual. More tourists, more shoppers. Watch your wallets (I’ve never been pickpocketed but I am very careful around the holidays anywhere). Chinatown, Times Square, and Rockefeller will especially be packed with people.
Ice skating in Bryant Park costs only the price of renting the skates, that’s fun to do in the winter, too (earlier in the day is less crowded).
Do you like chinese food? Joe Shanghai’s in Chinatown is fun (can be a bit of a long wait, but soup dumplings and low prices are worth it). You can skip it if you like – we like it because it’s a lot of good cheap food, it’s nothing crazy special. If you’re a vegetarian or like veggies, I’ve heard good things about Dirt Candy. Plenty of good places to get a burger. You probably want to balance expensive resturants with inexpensive, fun places to grab a bite.
I’m not really a good person to talk about NYC food, we either go to Joe Shanghai’s or Platters (look it up, very yummy), or we walk around and find somewhere random to eat. 😛