Re: Can you charter one way ?
Just out of curiosity, why would you want to sail to Bermuda without needing to; like if you are on your way to the Caribbean?
Newport to Bermuda is not a sail to be undertaken lightly & certainly not on a bareboat; they are just not maintained to ocean crossing standards. I've delivered many many bareboats to & from the Caribbean & I've spent many, many hours of those deliveries fixing things that really should have been fixed as general maintenance. Before you all out there jump all over me about taking a boat that's not up to par offshore, you are probably NOT professional sailors. If you want to work in this industry, especially doing bareboat deliveries, one must take whatever boat is offered, without complaint & say thank you, very very much, very very often, or you will not be offered another boat EVER AGAIN, & someone else will do the delivery (& all future deliveries).
Anyway back to the original question, you must cross the Gulf Stream & that can be a pretty difficult trip (see the tales of last year's southerly migration via Bermuda: 2011 North American Rally to the Caribbean (NARC); 2 boats abandoned, several people hurt & one fatality.
Fly over & rent a bareboat there.