I like the way you pulled your colors together in the family room. Very nice. It appears you have eclectic taste, as your sofa and chair look contemporary, as does the painting over the fireplace, and your coffee table is traditional.. That should make the updating of your dining room an easy and less expensive task. I'd start by removing the tablecloth. The floral arrangement on your dining table is very pretty. I can't tell exactly from the photos, but it appears to still be pretty fresh in appearance, not faded? If so, you could keep the florals, but change the container.
See how in the photo the container lifts the arrangement and makes a statement. This is something that you could easily do. I'm not suggesting that particular container (unless that's a look you like). I'm just showing it as an example of adding interest. Personally, I'd repaint the wall under the chair rail. I think that really dates the room. I'd repaint it the same color as the top portion, or maybe go one shade darker. But I'd definitely stay in the same color family. It will really brighten your room. The other benefit you'll get is that the bay window will have a much more pleasing look. See how the two colors break up the vertical flow around the center window. It's distracting. That is a gorgeous window, and if you eliminate that dark color I think your window coverings would suddenly appear "new". :) Additionally, the valance and tiebacks tie in the colors from the family room. I'm guessing the dining rooms is open to the family room. I can't tell from the photos. The other things I'd do is move the extra chairs. Do you have a guest room or other room where you could put them when they're not in use? You have a lovely home and an eye for creating vignettes. I think with very little attention, your dining room could be stunningly updated. :) Good luck and have fun.