West Dover, VT
Cost: $75,000 signup per family; $6,500 annual dues
Amenities: Private ski slopes, luxury clubhouse, golf course
How to join: Fill out an application here
The Hermitage offers 1,400 acres of snow untouched by the uninvited, a sprawling four-season ski lodge with a five-star hotel, an 18-hole golf course, and an 80,000sqft clubhouse that's one of the largest post-and-beam structures in the country. Bowling, fly-fishing, and concerts by the likes of Hall & Oates round out the offerings, which come with a hefty price tag. But with those amenities, we can go for that.