I love visiting places during quiet season, shoulder season. Whistler is certainly crazy busy in Winter, and also a paradise for mountain bike lovers in Summer. So, when is the best time for me to visit? -- Right before mountain biking season which is in May. :D
I love Whistler Village. Yes, it might be a bit pricier for accommodation, but it is so unbelievably convenient to see shops, restaurants and Whistler Mountain Gondola are all within walking distance. Hilton Whistler and Westin Whistler are both dog-friendly.
Get to know the local shops, cafes, restaurants and pubs.
There are so many lakes around Whistler. They are pretty too!