Choose a ski resort carefully to meet your family’s winter sports interests and abilities. If these vary, be sure there’s enough terrain to keep all levels of skier busy for a week. Most mountains have trails for all levels, but they may have only a few trails in some of them — especially beginner and expert, so those skiers can get tired of the same terrain day after day. If you have children who are beginning skiers, make sure there is a good lesson program geared to their age group.
Stay at or close to the slopes, so everyone can ski (or not ski) at their own schedule without messy transportation logistics. If older skiers want to check their skis after a morning on the slopes, they can spend the afternoon in the heated pool or spa, or reading in front of the fireplace. Both Stowe and Okemo in Vermont have large slope-side hotels where you can hop on a lift right outside the door.
If lodging is not slope-side, be sure the resort has a free shuttle bus so skiers have some flexibility and nobody has to sit in the base lodge waiting for others. Most large resorts do, including Bretton Woods and Waterville Valley in New Hampshire.
Choose a resort with multiple activities — a swimming pool, snowshoeing, a mountain coaster or tubing hill for the kids. And plenty of activities for non-skiers if anyone in the family doesn’t ski. Large resorts such as Deer Valley in Park City, Utah, have day spas, shops, cafés and sun terraces, and at many you can ride the gondolas to mountain-top restaurants for a scenic lunch.
Look for a condo with enough separate rooms so each couple can have a bit of space and privacy. A little togetherness goes a long way, especially for a whole week. Agree ahead of time that generations can go their own way without apology.
Don’t expect grandparents to babysit. Maybe they would cherish evenings spent with your kids while you have a quiet dinner for two, but don’t assume that or hint you expect it. If they don’t offer, one diplomatic approach might be to ask if grandparents would like to have a quiet dinner together without the children some evening, and assure them you won’t be offended. That gives them the perfect opportunity to offer you the same.
In finding out everyone’s expectations ahead of time, don’t forget to include the kids. If they don’t normally spend a lot of time with their grandparents, they may be anxious about spending several evenings alone with people they are not use to being with.