It depends on the city really. I find that some cities hotels are just a way better value but other time air b and b can be good. Like for cabins and beach houses for example.

Depends on the location and the number of people in your party. Sometimes it does work out cheaper to rent an apartment or even a house instead of several hotel rooms. Kitchen space is always a boon, I'm rarely impressed by overpriced restaurant fare and prefer to cook for myself when possible. It can also be helpful if you're traveling with pets.