You should be able to use a User-Defined Table for this.
For each image, enter the date that it would display (a Date field), the image (Image field) and text (Text field).
You can use filter settings on the table to show the correct image.
If you need to control the layout, use a custom XSL to render the table, although you'd have to manually define the filter within the XSL.
You should also visit Snowcovered to see if someone's already created a module that does this (I'm pretty sure there would be).