Planning a Multi-Family Hamptons Getaway

Some of the best vacations happen when a few families pool together under one roof. The Hamptons is made for it — and an oceanfront home that sleeps 12 to 16 turns a logistically tricky group trip into something effortless.

Here's how to plan a multi-family getaway that everyone remembers for the right reasons.

Pick a home with enough private space

The secret to a happy group trip is that everyone has somewhere to retreat. Our 8-bedroom home has two oceanfront master suites plus six more bedrooms — so each couple or family unit gets a real door to close. The 6-bedroom home offers the same with two masters and room for 12.

Divide the common space by time of day

With soaring ceilings, multiple living areas, and a big dining table, there's natural room to spread out. Mornings tend to gather around the kitchen and decks; afternoons revolve around the pool and the beach; evenings settle into the living rooms. Let the house's rhythm do the organizing.

Split costs the easy way

One home booked together is simple to divide: total the stay, split by family or by bedroom, and you're done. Compared with booking a stack of hotel rooms, a single house is usually both cheaper per family and far more fun.

Plan a few anchor moments

You don't need an itinerary, but a couple of shared anchors help — a group dinner cooked in (or catered) on the first night, a beach day, and maybe a North Fork wine outing or a trip to the Long Island Aquarium for the kids. The rest takes care of itself.