H1B and H4 - re entering the US close to expire date

[Amvargas76]

Hi everyone, I am an H1B VISA holder living in the US with wife and kid. My H1B VISA is in the first 3 years (no renewal so far) and it's up for renewal in September 2018. The VISA should be renewed unless I get my Green card first (fingers crossed I am in the green card process). My H1B expires on 17SET2018. I've been outside the US multiple times in this 3 years but my question is, since I always go on summer holidays, can I get back to the US with my family end of August 2018 when the VISA expires 17SET2018 (around 20 days after I get in. Again the renewal process should follow the regular steps (I am not aware of which ones since I never renewed, so I will have legal from my company let me know) but I just don't want to take the risk of being locked out of the US because I went on holidays.

Thanks in advance and if there's anything else you need to know to properly answer, let me know.