Hi Lee,
How incredibly special to be planning a trip for just you and your grandson!
You'll want to book a "Magic Your Way" package that includes your room, park passes and add the Disney Dining Plan to it. You'll likely just need the Plus Dining Plan that will give you one table service, one quick service and one snack per person, per night of your stay.
To make reservations to dine with characters, call 407-WDW-DINE, 180 days prior to your arrival. These are extremely popular, so you'll want to book as soon as possible. A few suggestions for character meals are: Chef Mickey's in the Contemporaray Resort (Mickey, Minnie, Goofy, Donald and Pluto) as well as the Crystal Palace in the Magic Kingdom (Pooh, Tigger, Eeyore and Piglet).
As far as where to stay, it really depends a lot on your budget and how much time you plan to spend at the resort. He's only 4, so he will likely really enjoy the
Value Resorts for their larger than life familiar icons. Check out the themes and see if there is one your think he'd like. The Value Resorts are the least expensive. However, they don't have a slide in the pool and are a bit farther away from the parks than the other resorts. My family has stayed in Value, Moderate, Deluxe and Villas and we've enjoyed all of them. If he really is a swimmer and you think he'd like a slide, you may want to upgrade to a
Moderate or
Delulxe Resort.
I'm out of room, but once you narrow down your choices, I'd love to help you with your final selection. Just send me any follow-up questions you may have.
Wishing you a wonderful vacation,
Kaylene