Hi Lisa!
Thanks so much for visiting the Disney Parks Moms Panel!
Resort hopping for dinner sounds amazing! Speaking from experience, it's absolutely fine to leave your stroller outside of the restaurant. When you check-in at each restaurant, I recommend you ask a Cast Member where you need to park your stroller. They will point you to a designated area for stroller parking.
Disney's Wilderness Lodge is always amazing but to stay there in December is practically perfect in every way! The rustic majesty of the Resort hotel combined with the holiday decorations is so welcoming! Plus - one evening, you can stay close to "Home" and enjoy a wonderful meal!
Story Book Dining at Artist Point with Snow White is absolutely charming! Snow White and her Disney Character friends are fun and the food is delicious! It's a must do while you are there!
I'm so excited for you! Seeing
Walt Disney World Resort through the eyes of a child is absolutely breathtaking! Enjoy every magical moment!
Thank you for sharing your question with the Disney Parks Moms Panel! My husband and I have made several trips to Walt Disney World Resort with an infant and toddler. Please let me know if I can help answer any other questions as you plan your magical vacation!
Kari