Property Caretaker

First Chair Destinations; Warren (VT); On-site; USD 30,000 - 42,000; Full time

Benefits offered by this job

Health insurance

401(k) with Company Match

Paid Time Off (PTO) & Holidays

Paid Flexible Time Off & Holidays

Paid Sick Leave

Job summary

First Chair Destinations in Vermont is seeking a Property Caretaker to support an assigned portfolio of vacation homes, handling owner and guest relations, maintenance, and housekeeping. You will work cross-functionally with the team to ensure high hospitality standards.

This role involves 30-40 hours per week, weekends and holidays may be required. A background in hotel or vacation-property operations is preferred, along with reliability, strong communication, and comfort with digital systems.

Qualifications

• Experience in hotel, hospitality, vacation or similar industry preferred.
• Minimum 1 year experience in housekeeping, maintenance or similar role.
• Excellent time management skills with the ability to change activity frequently.
• Strong attention to detail and reliability.
• Tech-savvy with experience using digital systems and apps.
• Willingness to travel between worksites and work independently.

Responsibilities

• Assist daily operations of the portfolio of homes and support process improvements.
• Respond to guest and homeowner concerns via emails, calls and tickets.
• Perform light maintenance such as bulbs, hinges, and unclogging a toilet.
• Conduct regular inspections prior to guest and owner arrivals.
• Collaborate with management on escalated issues and new units.
• Support cross-functionally across the team as needed.

Skills

Housekeeping

Maintenance

Time management

Attention to detail

Tech-savvy

Communication skills

Reliability

Independent work

Travel readiness

Tools

Mobile apps

Tablets

Software platforms

Job description

We offer exceptional vacation homes across the country’s most celebrated ski towns and coastal retreats. Each property is carefully selected, locally managed, and held to an uncompromising standard of care. We live and work in the communities we serve, which means every stay comes with generous local knowledge, genuine hospitality, and the confidence that what you booked is exactly what you’ll find.

We’re proud to offer a competitive benefits package designed to support our employees both at work and beyond. Benefits and eligibility may vary by position and are subject to change. Full plan details and terms will be provided during onboarding.

Health, Dental & Vision Insurance
401(k) with Company Match
Paid Time Off (PTO)& Holidays (non-exempt employees)
Paid Flexible Time Off & Holidays (exempt employees only)
Paid Sick Leave

Benefits are subject to the terms and conditions of the applicable plan documents, which govern in the event of any discrepancy. The Company reserves the right to modify, suspend, or terminate benefit plans and programs at any time.

About This Job

The Property Caretaker supports an assigned portfolio of vacation rental properties with responsibilities including all aspects of property management, including owner and guest relations, maintenance, and housekeeping. Supports cross-functionally across the team.

Compensation + Schedule

• $26 / HR less payroll deductions and all required withholdings
• Up to $100 monthly car allowance for eligible employees
• Schedule: 30-40 hours a week. Weekends required
• Weekends and holidays may be required

Essential Job Functions

• Assists in the daily operations of the assigned portfolio of homes. Identify areas for improvement, assisting managers in process enhancements to drive efficiency and quality outcomes.
• Support the team with escalated guest and homeowner concerns by responding to emails, calls and tickets.
• Perform light home maintenance (light bulbs, fix door hinges, unclog a toilet, etc).
• Conduct regular inspections prior to guest and owner arrivals.
• Works to resolve guest and homeowner concerns by responding to emails, calls and tickets. Partners with the management team on escalated issues.
• Partners and assists your Business Development Representative and management team when new units join the portfolio.
• Supports cross-functionally across the team as needed.
• Other duties as assigned because every day is different in hospitality!

Skills + Qualifications

• Experience working in hotel, hospitality, vacation or similar industry is highly preferred.
• Minimum 1 year experience in housekeeping, maintenance or similar role.
• Excellent time management skills with the ability to change activity frequently and cope with interruptions.
• Strong attention to detail.
• Tech-savvy with experience using various digital systems and applications and comfortable using mobile apps, tablets, and various software platforms.
• This role involves frequent travel between worksites, so reliable personal transportation is essential.
• Dependable and prepared. Showing up on time and ready to go is key to creating great stays for our guests and peace of mind for our homeowners.
• Must be dependable, self-motivated, and able to work independently while contributing positively to a collaborative team environment.
• Comfortable talking to people—online or in person—and being able to share information in a way that’s clear, thoughtful, and represents the company in a positive way always.

Workplace Environment + Physical Requirements

• Work may take place indoors or outdoors, in a variety of settings including private homes, resorts, offices, and laundry facilities — often in varying weather conditions.
• We’re in hospitality and our schedules can change based on guest and homeowner needs. Shifts may include early mornings, evenings, weekends, and holidays. We require flexibility to support this.
• Reliable transportation required.
• Regular travel within the locally assigned market and / or region.
• Ability to move freely (balancing, climbing, crawling, driving, squatting, standing, stooping, walking, bending, pushing, pulling, reaching, and repetitive hand/finger motions) and lift up to a maximum of fifty (50) pounds without assistance.

This job description does not identify every requirement of the position. First Chair may change position requirements, responsibilities, and work environment at any time with or without notice.

Some positions may require that you drive a personal vehicle and/or company vehicle for work purposes. Employees who are required to drive a personal vehicle must have reliable transportation, a valid driver’s license, and be at least 18 years of age. Employees who are required to drive a company vehicle must have a valid driver’s license, be at least 21 years of age, and have been a licensed driver for no less than 3 years.

An offer of employment for this role will be contingent upon the successful completion a background check.