Leadership Summits
Quiet rooms for big decisions. Wood-paneled breakouts and a fireplace for the long conversations that don't happen in a conference room.
Corporate Retreats
Where good work happens.
Two hours from Boston, just shy of three from New York, a quiet inn for leadership summits, off-sites, and the kind of conversations that need real time.
Host Your Next Retreat
A change of scenery, by design.
With flexible spaces and thirty-one guestrooms, The Whitlock is built for teams that want to get out of the office without sacrificing the agenda. Rich history, generous art, and a village full of detours, all framed by the rolling Berkshire landscape.
What We Host
Retreats of every shape.
Executive Off-Sites
Small senior teams, full days of focus, dinners that turn into nightcaps. Built for groups of eight to twenty.
Property Buyouts
The full inn, exclusively yours, thirty-one guestrooms and every common space dedicated to your team for the weekend.
Team Retreats
A productive change of scenery with hikes, drives, and group experiences across the Berkshires woven into the agenda.
Board & Investor Gatherings
Discreet, considered hospitality for the meetings that matter, annual board sessions, LP weekends, partner offsites.
Creative Workshops
Long-form working sessions for writers' rooms, design sprints, and brand summits. Bright rooms, good coffee, no clock-watching.
Ready to plan