I love your room! I actually like the chests there. What about putting vases on the chests, and you can get fresh flowers when you have people over? Or you could put shade-loving house plants on them...And a rectangular mirror on the long wall. I liked the stripes at first glance, but can see how you'd grow tired of them. Is there a neutral or light color in your chair cushions that you like?

Much better pics! I think the dining area is charming but definitely the scale problem. Can you even set 4 placemats on the table at the same time?

I do appreciate any and all advice, but I am (perhaps stubbornly) keeping the rug. I like the rug and I like that it hides the crumbs my kids drop every day until I feel like pulling out the vacuum. ;) It also helps to hide the fact that the table and floor are different tones.

I know it's hard to tell from the sideways photos in the OP, but I don't think the chairs are smooshed into the table at all. If you were looking down at the table from the ceiling, the table overhangs the chair seats by a little less than half. we only have to pull them out about 2" to sit.

I do have a leaf for the table. Would it look extra silly to have an oval table over a too-small round rug?

I don't use place mats, but yes, CF. Maybe the monster chairs are playing tricks here, but I think the table looks smaller in these pictures than it actually is. In reality it's 48" in diameter.

Might just be the photos! Yes, I do think oval table on small round rug would look silly. If you are getting rid of the chests, I think you'll want something to anchor those corners. Maybe some small demi-lune tables?

48" is plenty big for a small family...I think the chairs are a little large, but I like them so wouldn't want to replace them either. Plus you said you don't have a large budget, and a new table set, even if you re-finish an old one, is not going to be cheap. Since you said you don't like the stripes, I wonder if re-painting to start with would get the ball rolling.

I did refinish these chairs and the table (and chests) myself, so I'm not totally opposed to swapping them if I can find something wonderful to redo for the right price, but I haven't come across anything yet. Buying new is definitely not in the budget.

Paint the walls solid and maybe add wallpaper to the long wall with a buffet (if it fits). If buffet doesn't work, a corner type tall cabinet. You need a larger rug and if next size up doesn't work, get a square or rectangle. replace curtains with a lined linen curtain hung on rings.

Is the table short? I like the scale of the furniture you had before

Ok well if you want to keep everything as is, not much help anyone here can give. Maybe large art on the blank wall and remove the other two small picture frames

How tall is the table?

Another problem is round table, round chandelier and round rug.

I think the best thing to do is remove rug and add a rectangular one or square one if you really need it. It's an easy and inexpensive fix.

Then add buffet back and art above it with couple buffet lamps. You can try to put the buffet more towards the window side of that wall so it's not directly behind table.