Hakone in between Osaka and Tokyo

So we're planning on heading from Osaka to Tokyo near the end of our trip in March and are thinking of checking out Hakone. We'd like to do the Hakone Round Course loop to really take it all in.

For the loop, would it be better to settle down in Tokyo, then do a day trip to Hakone, or stop in Hakone for a night on the way to Tokyo from Osaka? We will have a JR pass, but I've seen that Hakone seems to have a special free pass.

What if we wanted an onsen night in Hakone? Any recommendations for places to stay (ryokan, minshuku, hotel) for the night at good locations on the loop?

You can do it either way you described. But you can obviously go slow and see more if you do an overnighter.

My recommendation is stay overnigjt in Hakone Yumoto, close to station. Not in Gora. You will arrive to JR Odawara and purchase Hakone Free pass from there. You go to your ryokan , drop your lugguage and go for loop course After that. Round course would need about 4-5 hours. Of course you can stay and explore More at different points . After round course you go to your ryokan for bath and dinner.

So just to clarify, you recommend staying in Yumoto because it would be easier in terms of dropping things off first, then travelling the round course without carrying everything?

I think that makes sense; it sounds a lot more daytrip-esque. I'm assuming then that we should head out early from Osaka and arrive at the ryokan around 8/9/10am to give us plenty of time for the day to do the round course before settling back at the ryokan for the evening...?

Just to throw this out there, if you arrive at Hakone-Yumoto Station before 1:00 pm you can pay to have any bags sent to your hotel and they will arrive later that day. There is a fee involved but it's not so high. Personally, I'd takyuubin my large bags from Osaka to Tokyo and just have an overnight bag or backpack or something else small, but that's just me.

I've stayed at: The Fujiya Hakone Yumoto (decent baths, was not impressed with anything else outside the location which was superb and perfect for arriving at Hakone-Yumoto after 9:00 pm) The original Fujiya (non-descript baths) lovely historic building and gorgeous grounds, OK location and very kind staff, the Kowakien Hotel, super convenient for Yunessun, and on a few bus routes, decent onsen in the hotel and I want to ay large room, it was in '09, And someplace near Gora which was the most affordable, enormous accommodations, and decent bath, unfortunately my friend booked it on a Japanese website so I don't know the name. It was surprisingly nice though. If I overnighted again I would either do the original Fujiya or try somewhere new since I can't find the place near Gora again.