Handling Lease Renewals During the Holidays: Strategies for Retention and Reduced Vacancy

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The holiday season is usually filled with travel, family commitments, and year-end financial pressure—not exactly the ideal time for a tenant to think about renewing a lease. That’s why many landlords experience avoidable turnover in December and January. The key to maintaining stability during this period is understanding tenant behavior, planning ahead, and offering the right incentives.

Below are practical, Maryland-specific strategies (especially relevant to Harford & Baltimore Counties) to help you boost tenant retention and minimize costly vacancies during the holidays.

1. Start the Renewal Process Early

Tenants are busy during November–January. If your renewal window opens in winter, communication should begin 60–90 days before lease expiration.
This gives tenants enough time to:

  • Plan financially

  • Ask questions

  • Communicate changes in family size or employment

  • Compare alternative options (and hopefully determine that staying is the best one)

Early communication sets a professional tone and demonstrates that you’re organized and proactive—a big plus for retention.

2. Offer Holiday-Friendly Renewal Incentives

Holiday budgets are tight. Landlords who recognize this can stand out by offering modest but meaningful incentives such as:

  • A small one-time rent credit (e.g., $50–$100)

  • A waived renewal fee (if applicable)

  • A free upgrade, like a new smart thermostat or LED lighting upgrade

  • Complimentary HVAC filter replacements or a winter maintenance check

These incentives often cost less than one month of vacancy, making them highly cost-effective.

3. Highlight the Benefits of Staying Through Winter

Moving during the winter—especially in Maryland—is inconvenient and sometimes dangerous. Remind tenants of the advantages of renewing now:

  • Avoiding winter moving costs

  • Guaranteed stability for children during the school year

  • Avoiding unpredictable winter rental rates

  • Avoiding the stress of coordinating movers, utilities, and address changes during the holidays

Framing renewal as the easier and less expensive choice can significantly sway decisions.

4. Communicate Maintenance Plans Clearly

Holiday and winter months come with increased maintenance needs. Addressing these proactively builds confidence.

Share your winter maintenance plan, including:

  • Emergency response procedures

  • Snow and ice removal expectations

  • Furnace or boiler inspection schedules

  • How to reach maintenance during holiday hours

  • New winterized features or improvements you’ve made on the property

When tenants trust that their home will be warm, safe, and well-maintained, they’re more likely to renew.

5. Evaluate Rent Increases Thoughtfully

Rent adjustments are normal, but the timing requires sensitivity.

Consider:

  • Keeping increases modest during the holidays

  • Aligning any increases with documented improvements or rising operating expenses

  • Offering tenants a multi-year renewal option to lock in predictable pricing

Tenants are far more likely to renew when they view the pricing as fair and justified.

6. Provide Flexible Renewal Options

Different households have different holiday and financial obligations.

Examples of flexible options include:

  • Month-to-month extension at a reasonable premium

  • A short-term extension (e.g., 3 months) for tenants with uncertain plans

  • A multi-year lease for long-term renters

  • A payment plan for renewal-related fees (if applicable)

Flexibility shows that you value the relationship—not just the contract.

7. Make the Renewal Process as Simple as Possible

A complicated renewal process is one of the most common reasons tenants delay or walk away.

Ensure you:

  • Offer digital signing (DocuSign, Adobe Sign, or your property management software)

  • Provide clear instructions

  • Keep renewal documents clean, concise, and easy to understand

  • Respond quickly to questions—especially during holiday travel periods

Convenience is a major factor in retention.

8. Conduct a Holiday Check-In

A brief email or text in early December can go a long way:

“Hi! As we head into the holiday season, please let us know if you have any questions about your lease or any maintenance concerns. We're here for you.”

This small gesture builds rapport and reminds tenants that they’re valued—not just rent payers.

Final Thoughts

The holidays don’t have to be a time of uncertainty for landlords. With early planning, thoughtful communication, and tenant-friendly incentives, you can dramatically improve renewal rates and maintain stable occupancy heading into the new year.

At Entrusted Property Management, we help Harford and Baltimore County landlords navigate renewal challenges with proven systems for communication, retention, and preventative maintenance. If you’d like help streamlining your lease renewal process this winter, we’re here to support you.

For more information on properties located in Harford & Baltimore County, MD, click here.