Personally I like Winterhold because it's way in the north and isolated. I like Falkreath.

Though not the most visually appealing city, I love Whiterun because of its location. Beautiful Whiterun mod fixes the blandness of it.

Falkreath is also nice because I love the surrounding forest.

Windhelm. A lot of people give it crap, but I like it, its a historically rich, ancient city with strong fortifications, 2 things I like.

Whiterun, always feels like coming home after going on an adventure.

Riften- "You will never find a more wretched hive of scum and villainy."

Plus I love the woods and the lake; it reminds me of home and the peaceful lifestyle I want if I get married.

Whiterun. It's truly a beautiful hold. Plains and sunny skies.

Mine used to be Solitude but now it seems Whiterun.

I really like Solitude, and in second place Whiterun. I like cities with "a lot of people". Windhelm is too cold for me.