Sure! This is the best time to visit Shillong as the rain would have finally stopped, waterfalls would be "water"full and roads would be filled with cherry blossoms.
you can take a direct flight from Delhi to guwahati and then take a shared cab from the airport to shillong (RS 500 per person) or you can hire ola/uber or private cab(which will cost Rs1500-2000approx).
Once you reach Shillong, you will find multiple hotel options in Police Bazaar or you can pre book on make my trip for homestays, guesthouses or hotels of your budget.
you can invest one day of your trip for a local sightseeing. Shillong has multiple tourist attractions like the Elephant falls, Laitlum canyons, wards lake which is in Police Bazaar itself, Shillong Cathedral, golflink(natural golf course), Sweet falls. Or you can do cafe hopping in the city and enjoy the local streetfoods.
1 full day will be required for a round trip to Cherrapunjee (which again has multiple places to explore)
Another full day for Dawki, Shnongpdeng and Mawlynnong (Asia's cleanest village and also has living root bridge)
I hope this is helpful and I would gladly help further if needed.
September to October is thr ideal time to visit Shillong, whether solo, with family or friends. To reach Shillong, one need to take a flight or train until Guwahati from Delhi. From Guwahati one can hire private cabs or get onto local transport to reach Shillong in about 3 hours by road. Once you reach Shillong, it will be the base to travel around Cherrapunji, Mawsynram, Dawki, etc.
Let me know, if you need details itinerary for a Shillong trip. I will be happy to help.