Hi Shannan,
The Villas at Wilderness Lodge is my family's Disney Vacation Club home resort. It really does feel like home to me, so cozy and inviting.
The villa kitchens are quite well stocked, but they do not include sippy cups. I would encourage you to bring a few from home if they're important to your family's mealtime. (They were completely indispensable to me when my girls were small.)
There are small plastic juice cups in the room, but they do not have a lid. As an alternative, you would be welcome to grab a supply of paper cups with lids from the quick service restaurant at the Lodge, but this would only really work if your child were able to drink from a straw.
For your reference, here's a link to a complete list of
supplies in the villa kitchens.
Good luck with your planning. Please let us know if you have addition questions.