Keep the Vacation Home—Without Losing the Family
A practical planning guide for families who want to preserve a camp, lake house, or beach house across generations.
Is This Book for Your Family?
A vacation home can carry generations of memories—but also expenses, competing expectations, and decisions no one wants to make. This guide is for families who want to address those questions before uncertainty becomes conflict.
You Want the Property to Stay in the Family
The camp, cottage, lake house, or beach house is more than real estate. It represents family history, traditions, and a place where future generations can remain connected.
You’re Unsure Whether Shared Ownership Will Work
Some family members use the property more. Some can contribute more. Others live far away or may eventually want their share in cash. Fair does not always mean equal..
You Want a Plan Before a Crisis
The hardest decisions are often postponed until a parent dies, the roof needs replacing, or one owner wants out. A thoughtful plan made in advance gives the family a better chance of remaining a family.
If any of these concerns sound familiar, the time to begin the conversation is before the property passes to the next generation.
Follow the Trail of Decisions
Preserving a vacation home requires more than placing it in a trust or LLC. First, the family must work through a series of practical decisions. The guide leads you through them in a sensible order.
01 — Should the Family Keep It?
Assess the emotional and financial readiness of your family to maintain the property for future generations.
02 — Who Should Participate?
Identify which family members will have ownership roles and how transitions will be managed.
03 — How Will Use Be Shared?
Establish guidelines for property use, including scheduling, guest policies, and personal belongings.
04 — How Will Expenses Be Paid?
Determine how taxes, insurance, maintenance, improvements, and unexpected repairs will be funded.
05 — What Happens When Someone Wants Out?
Establish a fair process for transfers, buyouts, disagreements, and – if necessary – the eventual sale of the property.
These decisions become the foundation for an ownership and governance plan built around your family—not someone else’s assumptions.
What Makes This Guide Different
More Than a Book—A Family Planning Process
Wanting to “keep the house in the family” is only the beginning. A successful plan must reflect who wants to participate, how the property will be used, how expenses will be shared, and what happens when circumstances change.
This guide helps your family move from a general hope to the practical decisions an attorney will need to create the right ownership and governance plan.
Family Stories
Recognize the patterns that allow shared properties to strengthen some families while dividing others.
Guided Worksheets
Give family members a structured way to record their goals, concerns, expectations, and financial limitations.
Plain-English Guidance
Understand the purpose of trusts, LLCs, use rules, expense provisions, buyout rights, and decision-making procedures.
Complete Sample Agreement
See how a family’s decisions can be translated into a workable legal framework.
Prepare your family before the legal meeting.
The guide does not replace individualized legal advice. It helps family members identify unresolved assumptions, understand their choices, and arrive at the attorney’s office with clearer goals and better questions.
Available in paperback and Kindle on Amazon
LifeCounsel exists to educate, inform, and inspire — so you can make better decisions for your family and your future.
Written by an estate-planning attorney who has helped thousands of families prevent conflict
Jesse F. Bifulco has practiced estate planning for approximately 30 years. His work focuses on preserving family wealth and preventing needless family conflict—including the particular challenges surrounding legacy vacation properties.
Vacation Home Planning Guide
Plan It. Share It. Keep It.
Behind every “camp,” “beach house,” or “lake house” there’s a history — part money, part memory. And the longer a family owns a vacation home, the more complex managing it becomes. Parents want fairness. Children want clarity. Everyone wants peace.
The Challenge: How to preserve a beloved family vacation home without destroying the relationships that made it worth keeping in the first place?
This book shows you how to get there.
The book includes access to a full set of downloadable printable worksheets for your own use, or to share with your co-planners.
These notes and worksheets will provide your attorney with a working draft of your agreement.
The Trail of Decisions
Planning to keep a vacation home for generations isn’t one decision. It’s a process and a path through major decision milestones.
Vacation Home Planning Guide helps you navigate the path.
The First Decision
Consider the options of whether to take your vacation home into your family’s future or liquidate the asset and distribute it among them.
What Counts for Membership?
Determine who is family . . . whether it is blood or something else that counts for inclusion in membership responsibilities and priveleges.
Sharing and Enjoying the Property for Generations
How will your family share the property, especially as the family grows? Learn about the strategies successfully used to determine what is fair when sharing a vacation property, and how to enforce the family rulebook while keeping disagreements out of court.
Fairly Assessing and Managing the Finances
Learn the strategies for successful management of the upkeep of the property. From taxes to maintenance and improvements, how to share the burden without breaking the peace.
Insulating the Property from External Threats
Strategies most common for protecting the property from vulnerabilities – like tax liens or lawsuits.
More to Know if You Need It
A full chapter of plain language explainers on how legal frameworks like branching, governance, trusts, and LLCs work to support the family goals for the property.
What You’ll Get
Stories that Resonate
You may find yourself inside one of the stories . . . these are fictional but based on the real issues families face. Each chapter begins with a relatable story, outlining how the friction inherent in sharing a vacation home can wear on the property and the family ties. Each chapter takes the lesson and explains the methods used to avoid conflict and restore peace.
Guided Exercises
After the story and discussion of the chapter’s main decision point, there is a focussed worksheet to guide you through your own evaluation of your property and family goals and how to apply strategies to mitigate conflict and maximize successful planning.
The book includes access to a full set of downloadable printable worksheets for your own use, or to share with your co-planners.
These notes and worksheets will provide your attorney with a working draft of your agreement.
Information
The Explainers chapter takes you through a deeper look at the concepts, showing how one choice versus another will play out over time. This chapter is written in plain language. A glossary of the terms used throughout the book is also included.
Full Sample Agreement
The final chapter presents a fictional family, and the circumstances they are working through in creating an agreement that will shield both their relationships and their property for themselves and their heirs.
The resulting agreement is presented, with references from and to the fictional family saga, to help you see how plain language goals are translated into “legalese” to help demystify the process.
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Check out LifeCast
Want the full conversation?
Every family thinks their vacation home will last forever — but most don’t make it past the next generation. Not because families don’t care—but because no one planned for what comes next.
In this episode of LifeCast, Attorney Jesse Bifulco sheds light on why a family vacation property rarely makes it past the second generation, and the difference between inheritance by default and legacy by design.
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In a related topic, find out how Timeshares can be managed in your estate plan.
Information provided for educational purposes only and does not constitute legal or investment advice, or create an attorney-client relationship.
For personalized guidance, please consult a licensed attorney or financial advisor.