For me, the best way to save money on winter (or anytime of year) travel is by cashing in my credit card rewards. Last year, my husband and I took our two kids skiing in Utah with several other families and we paid for the cross-country flights entirely on points and used straight cash-back rewards to pay down most of the cost of the Home Away rental. Ski trips are never much of a bargain but knocking out the cost of airfare and reducing the overall lodging made a huge difference. We also had a kitchen in the condo we rented so breakfast, dinner and snacks were mostly eaten there.
This year, we are taking them skiing in Vermont instead, mostly because its a LOT cheaper than skiing out West. My kids don’t know the difference and we will still have the exact same experience (snow, skiing, snowmen, mountains, etc) but at a fraction of the cost.
I also own two hotel credit cards which each give me one night free annually at a low to mid-range hotel in their portfolio. We used one night over Thanksgiving towards a three night stay in Orlando at a Residence Inn which also came with a huge free breakfast buffet. Last time we went to Orlando we were stuck paying for hotel breakfasts which is always overpriced and underwhelming. Between the one free night and three free hotel breakfasts for a family of four, we saved a ton. Oh yeah, there was a free shuttle to the parks too so no parking fees. I guess my tip is use points and try to eat for free