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Long-term Winter Rentals: The Pros, Cons, and Key Considerations

Joan Talmadge | Updated 9/5/2025
Long-term Winter Rentals: The Pros, Cons, and Key Considerations

Many Cape and Islands homeowners are tempted to rent out their otherwise vacant homes during the off-season. After all, bringing in some income seems better than leaving the house empty, right? Not necessarily. Before committing, it’s worth weighing both the benefits and the risks—and taking steps to protect yourself.


The Pros

If you won’t be using your home in the off-season, winter rentals can provide extra income—even at reduced rates. Most homeowners require tenants to cover utilities during the winter, which cuts your expenses compared to summer weekly rentals.

You may also encounter excellent tenants. Families between homes, teachers on sabbatical, or professionals on temporary assignment often prove respectful and reliable. In these cases, you also benefit from having someone watch over your home, rather than leaving it vacant and vulnerable.


The Cons

Rental income in the winter is drastically lower than in the summer, as demand drops and vacancies abound. Even at half your summer rate, you may find it underwhelming.

Long-term tenants also tend to be harder on a home. Unlike weekly vacationers, who spend much of their time outdoors and live lightly, winter tenants fully “move in.” They cook, clean, entertain, and simply live more intensively in the house, which increases wear and tear.


The Risks & Key Considerations

Some winter rental stories are truly cautionary: damage to walls, floors, and furniture; excessive trash; or broken doors and windows. Worse, Massachusetts tenant laws make eviction difficult—especially if children are involved. If a tenant refuses to leave in the spring, you could lose valuable summer weeks, or the time needed to prepare your home.

Legal & Regulatory Requirements

  • Mandatory lead paint disclosure and laws. Massachusetts requires owners of homes built before 1978 to comply with lead paint regulations for rentals exceeding 31 days.
  • Security deposit laws. For tenancies of 90 days or more, landlords must hold deposits in a separate Massachusetts bank account, per state law.
  • FHA and ADA compliance. Once a stay becomes a tenancy, landlords are subject to Fair Housing laws, which prohibit discrimination against protected classes, and may also need to make reasonable accommodations under the Americans with Disabilities Act.

Financial Risks

  • Greater financial risk. If a long-term guest demands money back or cancels close to their stay, you may be left scrambling to fill the vacancy.

Tenant Expectations & Challenges

  • Higher expectations. Winter tenants are more exacting than short-term vacationers. They’re more likely to demand prompt repairs and upgrades.
  • Exit strategy. Some renters refuse to leave when their lease ends, claiming they have nowhere else to go. Courts may grant them more time, delaying your summer season.

How to Protect Yourself

  • Screen thoroughly. Ask for references, verify employment, pull a credit report, and research prospects online. Meet them in person or virtually before committing.
  • Understand their reasons. Know why they need a long-term rental. Judges may be sympathetic if tenants argue they are using your home as a primary residence.
  • Use a strong lease. Consult an attorney to draft or review a comprehensive lease agreement that protects your interests and complies with state law.
  • Charge a higher deposit. The risks of long-term tenancies justify a larger security deposit.
  • Allow extra turnover time. Schedule more time between tenants for deep cleaning, maintenance, and provisioning.

Final Advice

Winter rentals can be a smart option—especially with respectful tenants and a well-written lease. But they carry trade-offs: lower income, more wear and tear, and potential legal complications. By screening carefully, setting clear terms, and understanding the laws, you’ll reduce your risks and decide whether a winter rental truly fits your needs.

About Joan Talmadge

About Joan Talmadge: In 1996, my husband Jeff and I purchased our Cape home and began looking for a way to rent it out during the summer. That's when Jeff created WeNeedaVacation, and the rest is history! After teaching fifth grade for 8 years and spending 15 years writing and editing educational publications, I found myself transitioning into a new career as a business owner. Today, we're fortunate to have a wonderful team of capable, caring staff, and Jeff and I are especially proud that two of our three grown children work with us. After 26 summers of renting out our home, we now live here year-round and couldn't be happier. The Cape truly is magical, no matter the season.