Just so you know, there is a difference between nasal _masks_, which fit over the nose, and nasal _pillows_, which seal directly against the nostrils.
Almost all nasal masks connect via a freely-rotating 90 degree connector at the front of the mask, so it is trivial to route the hose via the top of your head. Nasal pillows tend to connect via a fixed short length of hose coming out of the unit, typically in a downward direction. Depending on the stiffness of the hose, you can simply loop it around and route the hose over the top of your head as well. I have no direct experience with the Pilairo, so I don't know how easy it would be for that unit.
There are also commercially available hose hangers that suspend the hose above your head and keep it out of the way. Several people have created their own makeshift hose hangers out of coat hangers and attached it to their headboard.
Talk to your DME/supplier in trying different masks, you should be able to return mask within 30 days and keep trying until you find a mask that you really like . Everyone is different, I've tried variety of masks and settled on Activa LT nasal mask
The cushion quite flexible perfect for side side sleeping and vents extremely quiet
I also sleep on my side but with the mask, I no longer can sleep on my stomach. I've settled on the F&P Eson. Once I got the adjustment right, I eliminated pretty much all leaking and nose soarness. I tried the Swift fx nano which is similar to the Wisp except less head gear and no over the head hose holder; I found with that extra length of hose it pulling the mask down and created leaks, to illuminate these leaks I had to tighten the straps really tight that the mask was touching the tip of my nose, also the hose was getting caught underneath me when I turned from side to side. I asked my provider to swap the Nano for a Wisp to try which he's more than happy to do, but warned me that many have returned the Wisp for various reasons. Therefore I'll be swapping for another Eson to have as a spare.
Remember that everyone's face is a little different and what works for one may not work for another, I feel lucky that I was able to find a mask that worked for me after only trying 3 different masks, some may have tried 10 masks before finding the one that works for them.
BTW, the 3 things I like about the Eson is my hose connects directly to the mask, the connection is a ball and socket joint which gives the hose complete freedom to move without binding and pulling the mask away from my face and most importantly it has a clip on diffuser for the exhaust port that tremendously reduces the air blowing on my spouse. With the other two masks I tried she could feel the exhaust air blowing on her which made it impossible to sleep on that side facing her.
Good luck and I hope you find the mask that works for you!
I took the Wisp home and can't get it to stop leaking when it's loose enough to not put pressure on my sinus.
I am going back tomorrow to look into something else. I am thinking a straight nasal mask or whole face, even though I said I never would.
I am finding CPAP much easier to use than I thought it ever would be.
The new TapPap will be your "wonder mask"! I LOVE IT.
There is NO headgear at all and the hose directs up over your head. The nasal pillows connect to a mouthpiece which you slip onto your upper teeth. Since your teeth don't move, neither do the pillows!