Yes, a cloaking shield can be extended around a non-cloak capable vessel.
The cloaking device is an offshoot of shielding technology and can be tied into either the deflector shield or a ship's main shield and hence can be extended.
In TNG: "Devil's Due", the following exchange takes place;
PICARD : She has a Romulan cloaking device?
GEORDI : More likely, a bad copy of one. We picked it up through a wavelength stretchout...
PICARD : And the Enterprise?
GEORDI : Exactly where it's supposed to be. Ardra extended her cloaking shields around it...
In the episode VOY: "Tinker, Tenor, Soldier, Spy", the aliens are using a cloaking field which appears to extend to cover multiple vessels;
JANEWAY: I don't want to hear it. However, I would like to know why you've disobeyed my direct order.
EMH: I can prove it to you. The alien told me how to reconfigure our sensors to compensate for their cloaking field.
KIM: He's right. I'm picking up three ships out there. Distance six hundred million kilometres, headed right for us.
This obviously applies to standard cloaks. There's no in-canon way to tell whether this also applies to exotic cloak types such as the one used to cloak an entire planet in TNG: "When The Bough Breaks" or the Trans-phasic cloak used by the Enterprise in TNG: "Pegasus"