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The g1 Show Stable fits quite a few ponies in there neatly and is very easy to find and always cheap as it's such a common playset
Oh wow, that picture is awesome! Thank you guys for all your suggestions! I'm having way too much fun searching on ebay for all these things, and discovered, going by the first suggestion that fisher price little people also had a couple of castle versions as well as their farm (haha, if I can't have Dream Castle I still want a castle, dernit!) which looks like it can hold a decent number of ponies. Further exploring also led me to find the Dora the Explorer castle, which, as somewhat embarrassed as I am to admit, is also quite cute and looks an appropriate size as well Yay for having choices!
You can probably get something local on craigslist! The G3 Castles are plentiful right now!
Sylvanian/Calico Critter play sets and the like (there's a Target version of them whose name I can't recall) should also work.