Yes. In Skype, change your sound options to use the headset. Also, right-click on the sound icon in your system tray and go to Playback Devices. Under Speakers, right-click and "Set as Default Device"
Under "Headset Earphone" right-click and "Set as Default Communication Device"
This will allow you to accomplish what you are trying to do, for so long as both the headset and speakers are listed in the Sound options.