It's pretty much the same everywhere. All of these places have accommodations in the premium range as well as moderate range. Try homestays and hostels, I'm sure most of them have their online presence, or they must have some sort of presence on Google Business. Perhaps if you connect with them and explain that you're planning a longer stay, they could be flexible with the tariffs. Good luck! Looks like you are planning a trip to the hills! If you are travelling towards Chimney in Kurseong, do drop in at Lemo's :)
Darjeeling district in winter, huh? Which place offers the best bang for your buck, off the beaten path? For me, it's Kurseong! I found cozy, affordable homestays and stunning views without the Darjeeling crowds.