Problem is your ClientIDMode
property on Textboxes
ClientIDMode="Static"
You need to remove abvoe attribute from your GridView
code, because if you use it, all your TextBox
controls will have the same ID, "txtCheckoutDt_LodgingNLiving" for this particular control on it calender extender is set. The CalendarExtender controls will find the first value (which is on the first row) and will be all mapped to it.
If you want to refine the patterns of your control ID assignment, here's more about the topic.