When winter hits New England, Killington becomes the top spot for big group weekends — from college ski crews to 30–40 year-old friend groups booking a much-needed escape after the holidays. With long runs, great terrain, and nightlife that rivals any mountain town in the Northeast, Killington sets the stage for unforgettable winter trips.
Whether you’re renting a large Airbnb, planning a bachelor party, or bringing 20–40 people on a ski weekend, January through March is peak season — and the perfect time to lock in your plans.
College Winter Break Trips (NJ, NY, PA & Beyond)
Killington attracts thousands of college students every January. Groups from New York and New Jersey often book oversized ski houses along the access road, using the mountain as the backdrop for a full weekend of skiing, snowboarding, hot tubs, and late-night fun. If your crew wants a high-energy winter break with plenty of entertainment options, Killington delivers.
Guys’ Weekends & Bachelor Parties (Ages 30–45)
After the holidays, friend groups from NY, NJ, PA, and CT head north for a “winter reset” — a few days of skiing and blowing off steam. Many turn their weekend into a bachelor party or annual friends’ trip. Killington’s mix of outdoor activity, restaurant options, and private-house party setups makes it ideal for groups of 10–40.
Why Groups Choose VIP Entertainment
Since 1992, VIP Entertainment has helped ski-trip groups elevate their weekend plans. Our team makes it easy for groups staying near Killington, Pico, Rutland, and surrounding areas to line up professional entertainment for:
Bachelor parties
Ski-house weekends
College winter-break groups
Large Airbnb rentals
Reunion weekends
Birthday trips
With three decades of experience across New England, we know exactly how to help groups create a smooth, stress-free night that fits the vibe they’re looking for.
Booking for January–March 2025
If your group is heading to Killington this winter, it’s smart to reserve early — the busiest season begins right after New Year’s and stays strong until late March. Whether you’re a college crew or a group of friends planning your annual ski weekend, we’re here to help you make the night unforgettable.
To check availability for your Killington weekend, contact VIP Entertainment anytime. Call 802-342-4295 or fill out form