Staffing a Second Home or Seasonal Residence: How to Plan Winter and Summer Household Help

Seasonal households usually staff in one of three ways: a small year-round team that cares for the home, seasonal hires for the months the family is in residence, or core staff who travel with the family between homes. The right model depends on how long the home is occupied and how much care it needs while it sits empty.

That choice shapes everything that follows: who you hire, when you start looking, and who keeps an eye on the property in the off-season. Below is a practical way to plan it, drawn from years of running private homes from the inside.

What Is Seasonal Domestic Staffing? 

Seasonal domestic staffing means hiring or scheduling household staff around the months a residence is actually lived in. Think of a winter home in a warm-weather market, a summer house on the coast, or a mountain property the family uses for a few holidays a year.

The roles themselves are familiar ones: house managers, housekeepers, private chefs, nannies, and assistants. What changes is the rhythm. Instead of a team that works the same schedule all year, a seasonal home needs a plan for three phases: preparing the house before arrival, running it well while the family is there, and protecting it once everyone leaves.

Many families run their primary residence smoothly and assume a second home will follow the same pattern. It rarely does. A secondary residence often needs a different structure than the main home, which is why it helps to plan it on its own terms.

Three Ways To Staff a Seasonal Residence

Most second homes run on one of three models, or a blend of them. The deciding factors are how many months the family spends there and how much the property needs when no one is home.

ModelBest forAdvantagesTrade-offs
Year-round core teamHomes occupied several months a year, or large properties that need constant careContinuity, institutional knowledge of the house, someone always accountableHighest annual cost; staff need meaningful work during quiet months
Seasonal hiresHomes used for one defined season, such as winter or summerStaffing matches occupancy; cost tracks the months you’re actually thereRehiring risk each year; new staff must learn the home quickly
Staff who travel between homesFamilies with a trusted core team and a predictable travel patternFamiliar faces and consistent standards in every residenceTravel logistics and time away from home for staff; the empty house still needs local coverage

In practice, many families combine the different staffing methods. A common pattern we’ve noticed is a local house manager or caretaker who stays year-round, seasonal housekeeping and kitchen help during peak months, and a nanny or assistant who travels with the family. The goal is a structure where every phase of the year has a clear owner.

Which Roles a Seasonal Home Typically Needs

Not every residence needs every role, and some roles might overlap. These are the positions families most often consider for a second or seasonal home, starting with oversight.

  • House manager or estate manager: This is the person who holds the whole operation together. A house manager runs the daily life of a single residence, while an estate manager oversees larger properties, bigger teams, and often several homes at once.
  • Housekeeping: Seasonal homes need two kinds of cleaning: the elbow-deep work of opening and closing the house, and steady upkeep while the family is in residence. Plan for both.
  • Private chef: A chef matters most in homes built around hosting, holidays, or extended family stays. Seasonal chef roles are common because demand is concentrated in a few short months.
  • Childcare: If children come along, decide early whether your primary nanny travels with you or whether you need local childcare support at the second home.
  • Personal assistant: An assistant keeps travel, schedules, guests, and vendors coordinated across both homes, which is often where details fall through the cracks.

If you aren’t sure which of these your home needs, start with the oversight role. A strong house or estate manager will tell you quickly where the gaps are.

The Best Time to Start a Seasonal Staffing Search 

It’s best to start well before the family’s arrival date, because the best seasonal candidates commit early. Working backward from that date, the order looks like this:

  1. Confirm your occupancy dates. Settle when the family arrives, when it leaves, and which holidays or guest visits fall in between. Every other decision depends on these dates.
  2. Choose your staffing model. Decide which roles stay year-round, which are seasonal, and who travels with you.
  3. Define each role in writing. List responsibilities, hours, and who each person reports to. Seasonal roles fail most often when expectations were never spelled out.
  4. Begin the search at least 30 days before the season starts. Work with an agency that understands private homes, and give it the full picture: the property, the season, and your household’s standards. Most searches take two to six weeks, depending on how quickly decisions get made.
  5. Arrange a trial and a written agreement. A short trial confirms the fit in real life. A clear agreement covers dates, schedule, and duties so both sides start aligned.
  6. Prepare the home before arrival. Schedule the opening clean, vendor visits, and stocking so the house is ready on day one, not a week in.

The most common mistake is starting the search after the house has already been opened. By then, the family is living with gaps the staff should have closed.

Staffing and Caring For a Home While the Owner is Away 

An empty house still needs attention, and off-season problems are usually the expensive ones. A leak, a failed HVAC system, or a missed storm can go unnoticed for weeks if no one is checking.

Off-season care usually covers three areas:

  • Regular property checks. Someone walks the house on a set schedule, looks for damage, and confirms systems are running.
  • Vendor coordination. Landscaping, pool service, pest control, and maintenance continue in your absence and need oversight.
  • Opening and closing the house. Closing protects the home for the months ahead. Opening gets it guest-ready before the family returns.

In most households, this falls to the house manager or estate manager, either directly or by overseeing a local caretaker and trusted vendors. If your seasonal home has no year-round oversight, decide who owns these tasks before you leave for the season. 

What Changes Are Expected When Staff Are Short-Term or Seasonal 

The short answer: less than most families expect. A seasonal hire is still your employee. The relationship simply has defined start and end dates.

A few points to keep in mind:

  • You are the employer. When Domestic Bliss places a household professional, that person works for your household, not for the agency. Pay, schedules, and day-to-day management stay with you.
  • Federal rules still apply to part-year work. According to the IRS Household Employer’s Tax Guide, a worker can be your household employee whether the job is full-time or part-time, and whether you found them on your own or through an agency.
  • A vacation home counts as a private home. The U.S. Department of Labor’s guidance on domestic service notes that a private home can include a temporary residence, such as one a family uses while traveling, and that domestic workers in private homes are covered by federal wage law.
  • State rules depend on where the work happens. If your second home is in a different state, that state’s employment and unemployment rules may apply to staff working there. The Department of Labor keeps a directory of state unemployment tax agencies as a starting point.

This is general information, not legal or tax advice. A household payroll provider or employment attorney can confirm what applies to your situation.

How We Help Households Plan Their Seasonal Staffing

Domestic Bliss Agency was founded by Ashley Brown after more than a decade working inside private homes and estates. That experience shapes how we approach second and seasonal residences: we start with how the home is actually lived in, then build the team around it.

  • On-site planning. Our on-site household assessment covers new homes, second homes, and seasonal residences. Ashley looks at your occupancy pattern, travel, guest visits, and the months the home sits empty, then recommends the roles that fit.
  • Permanent and short-term placements. Alongside long-term hires, we offer temporary and short-term placements for travel, leave, events, and other defined periods.
  • A clear start. Where it makes sense, we arrange a trial period and help you put schedule, duties, and expectations in writing before the season begins.

Whether you need one seasonal role or a full plan for a second home, our household staffing process stays the same: unhurried, discreet, and focused on fit.

The FAQs We Hear the Most About Seasonal Staffing

How far in advance should I hire seasonal staff?

Earlier than most families expect. Starting early gives you a stronger candidate pool, time for a trial, and a home that is ready before you arrive rather than after.

Can my primary-home staff cover my second home?

Sometimes. Roles that move with the family, such as a nanny or personal assistant, often travel well. Roles tied to the property, like housekeeping and off-season oversight, usually need local coverage. Many families blend the two.

Do I need a house manager if the home is empty half the year?

Often, yes, because the empty months are when problems go unnoticed. That doesn’t always mean a full-time hire. A part-time house manager, or an estate manager who oversees several properties, can provide year-round oversight without a full-time role at every home.

Planning Staff for a Second Home?

A seasonal residence runs best when the plan is in place before the season begins. That means knowing which roles stay year-round, who travels with the family, and who looks after the house once everyone leaves. When those decisions get made late, the gaps show up on arrival day.

Domestic Bliss Agency can help you plan it the right way, from the start. During a private household consultation, we’ll:

  • Look at how your home is actually used: your occupancy dates, travel, guest visits, and the months it sits empty
  • Recommend the right staffing model, whether that’s a year-round core team, seasonal hires, staff who travel with you, or a blend
  • Define each role clearly so every person knows their responsibilities before day one
  • Lead a discreet, personal search for professionals who fit your household, for the season or for the long term

Every search is led by Ashley Brown, who spent more than a decade working inside private homes and estates. She knows what a well-run seasonal home looks like from the inside, and what it takes to get there.

Whether you’re opening a new winter home, preparing a summer house, or rethinking a second residence that hasn’t quite worked, the first step is having a conversation with us.

Picture of Ashley Brown

Ashley Brown

Ashley Brown is the founder of Domestic Bliss Agency and has spent more than a decade in the domestic staffing industry. She worked in Los Angeles as a nanny, family assistant, estate manager, and chief of staff, so she knows these roles from the inside. Since founding Domestic Bliss Agency in 2018, she has spent eight years helping ultra-high-net-worth families and entertainment professionals find carefully vetted estate and business staff they can trust. Ashley holds a BA and an MFA, and she brings both personal experience and genuine care to every placement, because she understands what it takes to keep a busy household running smoothly.

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