We loved our 4 night stay at the Pineridge - it is a huge hotel and one of the few remants of the Raj era that is cheap! We had the gigantic blue room that is pictures with the massive bay/turret window seat overlooking the Mighty Himalaya. It wasn't completely clean, but it was completely charming and the sheets were clean and crisp and they gave us extra heavy blankets!
It was winter when we visited, so it was freezing, but the staff brought up bundles of firewood and lit it for us and for about £1-2 per day it was lovely and cozy! Plus there was a huge clawfoot tub so we had a hot bath each morning before going out to the little bakery called Glenary's that was 2 mins walk down the Mall.
The hallways were empty and we nosed around a fair bit - if we had the money, I'd buy it and restore it to it's former glory. Darjeeling is one of my favourite places in India and for the same price as you'd pay for a basic boring guestroom, you get a quirky & cheap place to stay! I think we paid £10 or £12 a night and other boutique style hotels with character are all at least £25 to £100 per night. You could easily charge £100 a night if it had a good clean, lick of paint and some minor updates!