We have done this several times when my brother was living abroad, When he came home, rather than him spreading himself thin visiting everyone, we would all meet up for a week in a big shared house. We split the cost between three families - brother sister and myself. We stopped doing it a few years ago when the family just got too big as the children grew up and had partners etc.
Things I learnt:
Whilst collections of cottages are nice and give you a bit of privacy, they struggle for big communal areas. I'd go for a big house with a big kitchen.
Swimming pools and games rooms are a big bonus.
It really doesn't matter about the location - the aim is to spend time together and there is always something nearby the least promising area for day trips.
Split the cooking between you - we used to do one meal each. Some places offer catering, which is great for a special occasion.
We have great memories of these holidays, go for it!