A Hamptons residence can have dramatically different staffing needs depending on the time of year.
During periods of full occupancy, a household may be managing family members, guests, entertaining, childcare, meals, housekeeping, vehicles, vendors, outdoor spaces, and frequent schedule changes. When the principals leave, that same residence may become quieter—but it does not stop requiring professional oversight.
That creates an important question for homeowners in Southampton, East Hampton, Bridgehampton, Water Mill, Sag Harbor, and surrounding communities: Should you hire seasonal household staff or maintain a year-round team?
For many households, the answer is not simply one or the other. The most effective Hamptons household staffing structure may combine permanent professionals who maintain continuity with carefully selected seasonal staff who provide additional support when the residence is busiest.
Seasonal staff are generally best when workload increases significantly during the months your family occupies the residence. Year-round staff are better when the property requires ongoing management, maintenance coordination, housekeeping, vendor supervision, or preparation even when the family is away.
For some Hamptons households, a hybrid structure offers the strongest balance.
Lorraine Lee Estate Staffing’s guide to building the right domestic team for a seasonal estate explains why operating a seasonal residence requires planning before the principals arrive, throughout occupancy, and again when the home transitions into its quieter season.
The right decision starts by separating seasonal responsibilities from year-round responsibilities.
Seasonal household staffing means hiring private service professionals for a defined period when a residence experiences increased occupancy or workload.
For a Hamptons property, seasonal professionals might support the household during the family’s primary period of residence rather than remaining employed throughout the entire year.
These positions may include:
Seasonal staffing can be particularly useful when entertaining, childcare needs, meal preparation, laundry, guest turnover, transportation, and household activity increase sharply during occupancy.
However, seasonal does not mean informal.
Private household employees still need clearly defined responsibilities, schedules, compensation, reporting relationships, professional expectations, and appropriate screening.
Seasonal staffing may be appropriate when most of the work exists only while the family is in residence.
Consider a Hamptons home that remains lightly occupied for much of the year but becomes a busy family residence during the summer.
When the family arrives, the household may suddenly need:
Maintaining every one of those positions throughout the year may not be necessary.
A seasonal model allows the household to increase staffing around the period of highest demand without creating permanent positions for responsibilities that largely disappear when occupancy falls.
Several private-service roles can adapt well to seasonal employment.
Housekeeping needs often increase considerably when a residence is occupied by family and guests.
Seasonal housekeepers may support bedroom and bathroom upkeep, laundry, linens, guest preparation, household organization, and daily presentation.
Larger estates may add several seasonal housekeepers to an existing permanent housekeeping team.
A private chef may be particularly useful during periods when the family spends most days at the residence, entertains regularly, or hosts extended guests.
The role may include menu planning, grocery sourcing, daily meals, children’s meals, dietary accommodations, kitchen organization, and entertaining.
Families spending extended periods in the Hamptons may need additional childcare even if they already employ a nanny elsewhere.
A seasonal nanny or family assistant can help with activities, transportation, meals, children’s laundry, household organization, and changing summer schedules.
Larger residences may require more frequent support with outdoor furniture, deliveries, vehicles, trash, pool areas, guest setups, event preparation, and general property tasks while occupied.
The precise job description should reflect the estate rather than simply using a generic seasonal title.
Year-round staffing becomes more useful when significant household responsibilities continue even while the principals are away.
A secondary residence still has systems, vendors, deliveries, maintenance requirements, inventories, furnishings, vehicles, landscaping, security considerations, and projects.
Someone may need to ensure those responsibilities remain organized throughout the year.
Year-round positions commonly considered for complex seasonal residences include:
An estate manager may be particularly valuable when a family maintains several residences.
Lorraine Lee Estate Staffing’s guide to staffing multiple residences for one family explains why multi-residence households often benefit from centralized leadership combined with property-specific support rather than treating every residence as a completely separate operation.
This is one of the most important questions to answer before deciding that permanent staffing is unnecessary.
An unoccupied estate still requires attention.
Depending on the property, year-round employees may:
The goal is not to create unnecessary work when the family leaves.
It is to determine whether the residence has enough legitimate ongoing responsibility to justify maintaining permanent personnel.
One of the greatest advantages of a permanent household team is institutional knowledge.
Experienced year-round staff learn how the residence operates.
They know the preferred vendors, household systems, principal preferences, inventories, guest routines, maintenance history, service standards, and communication structure.
That knowledge becomes particularly useful when preparing the residence for the family’s return.
Instead of rebuilding the operation every season, a permanent manager or senior employee can coordinate preparations well in advance and help onboard seasonal employees into an established system.
Lorraine Lee Estate Staffing’s article on stability, trust, and long-term household teams also explores why continuity can become particularly valuable for families operating complex or multiple residences.
For many Hamptons estates, the strongest option is a year-round core team supported by seasonal staff.
For example, a residence might maintain:
Year-round:
During peak occupancy:
This arrangement preserves continuity while allowing the household to expand when activity increases.
Lorraine Lee Estate Staffing’s guide to temporary versus permanent household staffing discusses a similar distinction: ongoing responsibilities often justify permanent employees, while temporary professionals can help absorb predictable increases in seasonal workload.
The exact structure depends on the household.
A smaller Hamptons residence may need only one permanent house manager plus seasonal housekeeping. A larger waterfront estate with multiple buildings, sophisticated systems, extensive grounds, and frequent entertaining may require a substantially larger permanent team.
A Hamptons staffing decision should rarely be made in isolation when the family owns several homes.
Some families divide their year among New York City, the Hamptons, Palm Beach, Miami, Aspen, or other destinations.
In that situation, consider whether some employees should:
An experienced professional who understands the family’s preferences across residences can provide valuable consistency.
The Lorraine Lee Estate Staffing guide to staffing multiple residences for one family offers additional guidance on creating clear reporting structures and maintaining consistent service across several homes.
One mistake is treating a short-term position as though screening matters less.
In reality, seasonal employees may enter bedrooms, kitchens, offices, children’s areas, vehicles, storage spaces, and other private areas of the residence.
They may also learn detailed information about the family’s routines and travel schedule.
Seasonal candidates should therefore be evaluated with appropriate attention to:
Lorraine Lee Estate Staffing’s guide to what makes candidates successful in the Hamptons market explains why private-residence experience is only one consideration. Discretion, adaptability, communication, judgment, reliability, and professional boundaries also matter.
Seasonal staffing is easier when households plan before the residence becomes busy.
Waiting until the household is already fully occupied can create pressure to make a fast hiring decision.
Instead, establish the position early.
Before beginning a search, determine:
Clear expectations make it easier for candidates to determine whether the opportunity is realistic for them.
They also reduce the risk of discovering after hiring that the employer and employee had very different ideas about the position.
Whether an employee is seasonal or year-round does not eliminate the need to understand household-employer responsibilities.
The New York State Department of Labor’s Domestic Workers’ Bill of Rights explains employment protections that apply to domestic workers in New York, including requirements involving wages, overtime, rest, and other workplace protections.
Household employers should also be aware of insurance obligations. The New York State Workers’ Compensation Board provides information on workers’ compensation requirements for household employers and domestic workers.
At the federal level, IRS Publication 926: Household Employer’s Tax Guide explains how to determine whether someone is a household employee and outlines federal household employment tax responsibilities.
The IRS notes that worker classification depends largely on whether the household controls not only what work is performed but also how the work is performed.
Families should work with qualified payroll, tax, insurance, or legal professionals for advice specific to their household and current employment arrangements.
| Consideration | Seasonal Staff | Year-Round Staff |
|---|---|---|
| Best for | Predictable periods of increased activity | Responsibilities continuing throughout the year |
| Continuity | May change each season | Strong household knowledge over time |
| Property oversight while away | Limited unless specifically included | Can provide ongoing oversight |
| Peak-season flexibility | High | May still require added seasonal support |
| Onboarding | Often repeated each season | Less frequent |
| Multiple residences | Useful for property-specific coverage | Valuable for continuity across homes |
| Entertaining periods | Can expand the team quickly | Provides core leadership and standards |
| Long-term household knowledge | More limited | Usually stronger |
Neither model is automatically superior.
The correct choice depends on how the family actually uses the residence.
If the home is used only briefly, a larger permanent team may not be necessary.
However, occupancy is only one part of the decision. Property management, renovations, vendors, landscaping, security, and preparation may continue throughout the year.
If vendors, systems, renovations, housekeeping, vehicles, and maintenance still require regular attention, permanent staff may be appropriate.
Large gatherings and frequent guests can significantly increase seasonal staffing requirements.
Even households with a permanent team may need additional housekeepers, chefs, servers, drivers, or property support during periods of heavier entertaining.
A multi-property staffing structure may allow some employees to travel or coordinate between locations.
It may also make sense to maintain property-specific staff while placing senior oversight under an estate manager or director of residences.
If knowing the family’s preferences, vendors, household systems, and routines is essential, retaining a permanent core team can provide meaningful value.
Year-round staffing should not simply mean keeping every peak-season employee on payroll regardless of workload.
Instead, identify which responsibilities genuinely continue.
A large seasonal household may operate efficiently with a smaller permanent team that expands when the family returns.
For example, an estate manager and executive housekeeper might maintain the residence throughout the year. Before peak season, they could oversee the arrival of additional housekeepers, culinary staff, childcare professionals, or housemen.
This approach helps preserve institutional knowledge without creating unnecessary overlap.
The opposite problem can also occur.
A household may attempt to operate throughout the summer with the same small staff that manages the property during quieter months.
As occupancy increases, those employees may suddenly be expected to absorb additional housekeeping, cooking, transportation, guest support, events, childcare, laundry, and property responsibilities.
That can place pressure on otherwise strong employees.
Seasonal support can help keep workloads realistic and allow permanent staff to remain focused on their primary responsibilities.
Adding seasonal employees to an existing household team requires a clear reporting structure.
Every employee should know:
In a larger estate, this may be the estate manager or household manager.
Without a clear chain of command, even experienced staff can receive conflicting directions, duplicate tasks, or unintentionally bypass household leadership.
Technical experience matters, but successful private service also depends on personality and communication.
A Hamptons household that entertains frequently may need professionals who remain calm and organized around guests.
A family-centered residence may prioritize employees who understand how to work discreetly around children and extended family.
A highly formal estate may place greater emphasis on established service standards.
Before recruiting, define not only what the employee must do but also the environment in which they will be expected to do it.
This is particularly important for seasonal hires because they may have less time to learn the household organically.
Neither is inherently better. Seasonal staffing is useful when responsibilities rise mainly during occupancy, while year-round staff provide continuity and ongoing oversight. Many larger Hamptons residences benefit from a permanent core team supported by additional seasonal employees during busier periods.
Estate managers, house managers, executive housekeepers, property managers, and other professionals responsible for ongoing property operations are often strong candidates for year-round roles.
The decision should depend on whether their actual responsibilities continue after the principals leave.
Yes. A seasonal private chef can be appropriate when regular meal preparation and entertaining occur primarily during the family’s period of residence.
The job description should clearly define dates, schedule, dietary requirements, entertaining expectations, grocery sourcing, and kitchen-management responsibilities.
Seasonal household professionals should still be carefully screened.
Even a short-term employee may have access to the residence, family schedules, children, possessions, vehicles, and private information. References, experience, background screening, confidentiality, and personality fit remain important.
Year-round employees or designated property professionals can coordinate maintenance, vendors, housekeeping, repairs, inventories, projects, security, and preparation for the family’s next arrival.
If no permanent employees remain, those responsibilities should be assigned to appropriate external providers or management professionals.
Some households structure positions this way.
Whether it works depends on the employee’s role, schedule, compensation, travel expectations, accommodations, and responsibilities at each residence. Those expectations should be discussed clearly before hiring rather than added informally later.
Recruiting before the residence becomes busy gives the household more time to define the role, evaluate candidates, complete references and screening, and arrange onboarding.
Earlier planning can also make it easier to build a coordinated seasonal team rather than filling positions reactively.
A seasonal residence should feel effortless when the family arrives—and remain professionally cared for when they leave.
Lorraine Lee Estate Staffing works with private households and family offices seeking experienced household professionals for seasonal, permanent, and multi-residence positions.
Whether your Hamptons household needs an estate manager, executive housekeeper, private chef, nanny, house manager, or an expanded seasonal team, the recruiting process should begin with how your family actually uses the property.
Learn more about building the right domestic team for a seasonal estate or contact Lorraine Lee Estate Staffing to discuss the staffing structure that best fits your household.
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