Best bedside system, unit?

I just got a sonos play 3 for my bedroom, definitely worth considering. I think the 5 has a headphone out.

Squeezebox radio i use is great. There is a new but similar looking model. The sound quality is very good. Plays intefnet radio an music server.

Cambridge Soundworks gear may fit your bill nicely. Check their website for various models.
Bose and Yamaha has table top systems worth a look see.
McIntosh has a two new small systems should Santa have reason to believe you have been awfully nice this year.
Pending your budget there are some nice units to fill your need. Good hunting.

TIVOLI AUDIO

http://www.tivoliaudio.ca/

I just bought a Squeezebox Radio for exactly the same thing as you are wanting it for. It's a fantastic unit!

Another thumbs up for Squeezebox Boom radio. Great unit and alarm clock is programmed to fade in favorite music.

I WISH i knew more about the Squeezbox unit, so i can't compare the sound quality to what I own- the Tivoli #3 radio, companion speaker (for stereo), CDP, and Subwoofer. all these pieces can probably fit on two opposing night stands with your ears in the middle. the sound is sublime on just about everything. the best sound on jazz piano trios/quartets, vibraphone, , but it does pretty good on classical, rock,
etc. the reception is really good with the cheapo wire antenna provided, so you
could imagine what adding a really good antenna would result in.
The cherry wood cabinets are also very attractive (IMO). i just wish someone
would modify one of these radios and the subwoofer to increase the performance even more. the subwoofer does a good but not great job, and
there is a limit to how loud it plays. but i personally love listening to the radio
late at night and there is always something to tune in to, including talk.