I've thought about a similar strategy for traveling resort to resort out west. I think it would be a blast. I have done a fair bit of towing a Coleman pop-up with a compact pickup but pop-ups are no good for winter time. Hard sided travel trailers would work. I would like to get a small fiberglass camper like a 13 foot scamp. It's doable with a minivan as long as you stick to the absolutely smallest trailers out there and don't load up the trailer or van with too much stuff but you'd be much better off with a small truck; 4-5k lb towing capacity vs 3-3.5k for a mini van. Here's another place where GM dropped the ball dicontinuing the Astro/Safari vans. They were available in AWD and could tow 5k.
"You want your skis? Go get 'em!" -W. Miller