In the mecca of man-fur and monstrous third homes that is Aspen, it is possible—even probable—to plan a ski weekend for less than $500 per person. There are two tricks to this.
1) Timing is everything. Plan your visit in early or late season, when lodging rates are lower. Luckily, that includes a good chunk of the season—December until Christmas, January through the X Games, and late March and April—when (bonus!) the slopes aren't crowded and the snow can be excellent.
2) Be flexible. Don't set your heart on slopeside accommodations in Aspen. Instead, nearby Snowmass (20 minutes from town) can be a gold mine of lodging deals and virtually all of it is ski-in, ski-out. Dining is generally more affordable just outside Aspen, too. Take advantage of happy hours and liquor stores, eschew sit-down dinners and keep an eye out for freebies, such as coffee and granola bars on the mountains and free skier shuttles.
For lodging or ski-and-stay packages, check out Stay Aspen Snowmass, the local central reservations agency, which sells nearly 4,000 short-term beds. Using its search function, rooms start at $140/night at the Snowmass Inn for a two-night early January stay; in December, multiple options are available in Aspen and Snowmass for under $200/night.
In Aspen, the St. Moritz Lodge has a long, proud history of housing budget-minded ski bums, with shared hostel rooms starting as low as $57 per night and a range of lodge rooms and condos for less than $100 per person. The Tyrolean is another affordable option. Its most expensive room (which can sleep up to five people and has a full kitchenette) is $350 per night.
This can be the tricky part. With single-day lift tickets creeping into the $150 range, the best deals are found by bundling lodging and lift tickets through Stay Aspen Snowmass. That'll get you two days of schussing for $118 through December 18, and $198 most of the rest of the season. Without lodging (say if you're crashing on a friend's couch), a two-day advance ticket purchased through Aspen/Snowmass is $186 early and late winter, and $250 the rest of the season. If you plan to come back or extend your weekend, a four-day Classic Pass (also requiring advance purchase) breaks down to $65/day. College students coming for the X Games can score the best deal—a two-day X Pass is just $87. Of course, you can also earn free turns by skinning up the slopes (a popular choice these days, as long as you adhere to the resort's uphill ski policy) or touring the backcountry.
EAT AND DRINK HERE:
With nearly 100 restaurants in Aspen alone, dining choices—and prices—run the gamut. A proper sit-down dinner can easily drain the budget, but many finer eateries offer bar menus, scaled-back, lower-priced versions of the regular menu available only in the bar area. L'Hostaria is a local favorite, with housemade pastas for under $13. Jimmy's serves a nightly bar special for $14 (prime rib on Saturdays).
Good, cheap options flourish during happy hour, like $7 pizzas and $3 Red Stripe at Mezzaluna, 50-cent wings and beer specials at Zane's (in Aspen and Snowmass), and Hooch's $15 beer and bahn mi. For $2, swill the ski bum staple, PBR, at the Red Onion (during two happy hours, 3-6 p.m. and 10 p.m. to midnight) or Bud Light at the Limelight from 3-7 p.m.
Skip full table service, and get an amazing tuna burger and fries at CP Burger for $12 or a ginormous $5 slice at New York Pizza until 2 a.m. Ajax Donuts operates out of bright-red wagon, serving myriad munchies apres-ski and late night.
Besides free continental breakfast in some lodges, the best breakfast deals are Paradise Bakery muffins and a filling $5 breakfast burrito, while supplies last, at Big Wrap.