Hi Toby,
A couple of months ago, I switched my site over to SquareSpace and had the same problem: Google was able to index my pages, but was not indexing my images. I contacted SquareSpace Help about this and here is their answer:
"I've spoken to our advanced testing team and we believe that your images are indeed being indexed, although they are not being linked to your site within Google Search Console. However, they are being linked to your site in Google Search results. I'll explain why we believe this below:
The reason for this is that Squarespace images are on a CDN which has a separate URL (static.squarespace.com). While Google can find, index, and correctly associate the images with your site, they can't report this information back to your via Google Search Console as you are not a verified owner on eitherstatic.squarespace.com or static1.squarespace.com (the URLs on which the images are stored).
As long as images are being indexed and associated with your domain, there's no issue or cause for concern. I have done some digging and on my end can see that your images are being indexed and associated with your site correctly."
Hope that answers your question.
I would be interested to know if you are still using SquareSpace for your website and how you're doing with SEO, as I have encountered a number of problems, especially around meta-titles and meta-descriptions.
Thanks,
Monica