Most people drive here from Boston, New York or the Connecticut corridor - and the drive up I-91 through Vermont is genuinely pleasant, one of those routes where you stop watching the GPS and just look out the window for a while. From Boston its about 3 hours, from New York closer to 4 depending on how long it takes you to actually escape the city. No practical flights serve Rutland so a car is just part of the deal. Plan accordingly.
Burlington airport is the nearest real option if youre flying in - about 70 miles north on Route 7, rental cars available, and the drive south through Vermont takes roughly 90 mins and is beautiful enough that it almost feels like the trip has already started. Albany works too for travelers coming from the south or west, roughly 90 mins in a different direction. Both fine. Depends where youre coming from.
Once youre at the inn everything is car dependent - thats rural Vermont and theres no point pretending otherwise. Ski days you drive to the mountain. Dinner you drive to Rutland. Everything else same. But guests who come prepared for this dont miss urban transit for a single second. The ones who dont come prepared... learn fast. Usually day one.
Killington village runs shuttle service during ski season which is genuinely useful on heavy snow days when mountain road driving gets interesting. Pico is smaller and more self-contained. Ask staff about current schedules on any given winter morning - they follow conditions closely and give straight answers, not vague ones.
Parking at the inn is big, free and never a problem - ski gear, roof boxes, boot bags in the back, all handled without drama and theres always space. After one experience with resort parking at a bigger mountain you will actively appreciate this every single time. Not an exaggeration!