Here's my input....
1.) You need to specify when the seasons begin. And since they shouldn't overlap, and there shouldn't be any "non-season" time, the beginning of one will also mark the end of the previous. Something like:
Summer: May 5
Fall: September 20
Winter: November 30
Spring: March 1
2.) You need a way to know when the days fall in two different seasons, and how many days per season there are. This is just a matter of comparing time-stamps and precise calculation. You'd need to take the first date, and the date of the new season, subtract them, then mathematically solve for the number of days that is. THen you take that new season date, and subtract it from the end date, and solve for days. Now you have two lengths for each seasonal stay.
3.) You need to specify what price for what season, and even what price per destination per season. I'm sure you've got this done already 🙂
Hope that helps.....