Why not try a coach holiday, which includes, all the amenties, as well as bed breakfast and eveving, meal, which you don,t have to worry about, so you can go sight seeing, with the coach trip, or go solo, your choice,
I used to live in Whitby, its a great place with lots of interesting things to see and also close to the moors for some beautiful walks. I always stay in self catering when i travel. Either use air bnb or Sawdays, also through instagram. I started house and petsitting a few years so tend to do that instead now.