Winter squash and squash in general make very big plants and most of them are of the trailing variety rather than bush form. I think you will find they take up too much space in the greenhouse.
Outside, you can always stop the plants once the number of fruit you want have formed. As a general principle, the plants will go on setting fruit until the end of the season, but the later they are, the smaller they will be. The variety you are growing are quite small, around 500g per fruit, so I would allow the plants to form ten or so where you have space. In the greenhouse, to prevent the squash plant taking it over, you would be better to stop the plant after three squash and pinch out all the growing points. This will give you earlier fruit but less.
As you are growing all of them in large containers, make a wigwam or tripod of stout canes and grow them vertically. This will prevent them from taking up so much space. The fruit will hang down quite happily without falling off or you can net them like melons to be sure.

Thanks very much I am already begining to regret plant in greenhouse they are already to big to move outside.