Keeping the Family Vacation Home in the Family

Every year around the end of June, the same thing happens in New York City.

The streets get quieter.  Restaurant reservations suddenly become easier to get.  Even the traffic seems…almost reasonable.

For a brief moment, I start wondering whether everyone knows something I don’t.

Then it hits me.

They’re all in the Hamptons.

Or upstate.  Or at the Jersey Shore.  Or escaping to a family lake house for the long holiday weekend while the rest of us enjoy Manhattan with a little extra elbow room.

As estate planning attorneys, however, those summer getaways remind us of something more important.  Behind many of those vacation homes are decades of family memories—and one question that often hasn’t been answered:

What happens to the family vacation home after you’re gone?

For many families, a vacation home is much more than another piece of real estate.  It’s where children learned to swim, grandparents hosted Fourth of July barbecues, cousins stayed up too late playing board games, and generations gathered around the same dinner table summer after summer.

Parents often tell us, “We’d love for the kids and grandkids to keep enjoying the house.”

It’s a wonderful goal. But it rarely happens by accident.

Why Vacation Homes Can Create Family Conflict

Leaving a vacation home equally to your children may seem like the obvious solution.

Unfortunately, equal ownership doesn’t always lead to equal happiness.

• One child lives nearby and uses the home often.  Another lives across the country and visits once a year.

• One sibling has the financial ability to contribute to taxes, insurance, and repairs.  Another is raising young children and simply can’t afford unexpected expenses.

• One wants to renovate the kitchen.  Another wants to keep everything exactly as Mom and Dad left it.

  
  

And what happens if one sibling wants to sell while the others want to keep the property?

Without a clear plan, cherished family traditions can quickly give way to disagreements.

Planning Beyond the Transfer

One family I worked with loved the idea of their children and grandchildren continuing to gather at the family vacation home long after they were gone.  They also recognized that the biggest challenge wouldn’t be deciding who inherited the property - it would be paying for it.

So instead of simply leaving the house to their children, they arranged for additional funds to be held in trust to help cover real estate taxes, insurance, maintenance, and routine repairs for the first ten years after their deaths.

Their reasoning was simple: don’t let financial pressure force an immediate sale before the next generation has the opportunity to build its own memories.

Those ten years also gave the family time to decide whether keeping the property remained practical, rather than making a rushed decision because a new roof or a large tax bill arrived at the worst possible time.

Every family’s circumstances are different, but thinking beyond who inherits the house and considering how the house will be maintained can make all the difference.

Don’t Forget About Ancillary Probate

Many New Yorkers own vacation homes outside the state - a cabin in the Poconos, a cottage in the Berkshires, a winter retreat in Florida, or a beach house on the Jersey Shore.

What many people don’t realize is that owning real estate in another state can complicate estate administration.

If your vacation home is titled in your individual name when you pass away, your family may need to open an ancillary probate proceeding in the state where the property is located, in addition to any probate proceeding in New York.  That can add time, expense, and unnecessary stress during an already difficult period.

Depending on your circumstances, owning the property through a revocable trust or another appropriate ownership structure may help simplify the transfer and avoid additional probate proceedings.

Questions Worth Answering Now

A thoughtful estate plan can answer questions before they become disagreements, including:

• Who is responsible for taxes, insurance, and maintenance?

• How will major repairs be approved and paid for?

• Will there be a schedule for using the property?

• Can an owner rent the home to others?

• What happens if one sibling wants to sell?

• Does the family have a process for buying out another owner’s interest?

• Is there funding available to help preserve the property for future generations?

There is no one-size-fits-all solution.  Some families use revocable trusts.  Others benefit from a family LLC or more detailed trust provisions that establish rules for ownership and management.  The best plan depends on your family, your goals, and the property itself.

Protecting More Than Property

The Hamptons beach house, the Berkshires cottage, the Poconos lake house, or the Adirondacks cabin may represent a significant financial investment.

But for most families, its greatest value isn’t measured in dollars.

It’s measured in birthday celebrations, summer cookouts, grandchildren catching their first fish, rainy-day card games, and traditions that span generations.

Thoughtful estate planning isn’t just about transferring property.  It’s about giving your family the best opportunity to continue making those memories together.

If your family owns a vacation home and you’d like to discuss the best way to preserve it—or determine whether keeping it in the family is the right choice - an experienced estate planning attorney can help you develop a plan tailored to your family’s unique circumstances.

Out in the Community

Michael at the 2026 NAELA Annual Conference (Bernie Brewer to the right)

If you are a community group or work with social workers who need CEU credit and want to explore an educational session with Michael this coming fall, please VISIT.

In the meantime, we are enjoying the summer and hope you are too!