Sign up to access all features of our service.
  • Job search
  • Favorites
  • Create a CV
    New
  • Salaries
  • Subscriptions

Property Caretaker

$25 - $26 per hour

First Chair Destinations

Job Description

Job Description

A Little Bit About Us

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.

Benefits

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

  • $25 - $26 / HR less payroll deductions and all required withholdings
  • Up to $100 monthly car allowance for eligible employees
  • 20 - 30 hours weekly
  • Schedule: Varies weekly
  • 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 of  a background check.

Vacancy posted 1 day ago
Similar jobs that could be interesting for youBased on the Property Caretaker in Wilmington, VT vacancy
  • $18 - $21 per hour

    ABOUT THE ORGANIZATION Community Health Programs (CHP) is a mission-driven, nonprofit network of health centers dedicated to nurturing and inspiring healthy lives for people throughout the Berkshires. Our mission guides everything we do: delivering exceptional,...
    Suggested
    Hourly pay
    Full time
    Part time
    Work at office
    Flexible hours

    Community Health Program Inc

    Wilmington, VT
    5 days ago
  • Job Title Retail Sales and Service Technician (SST) Job Category Retail Position Summary The retail Sales and Service Technician (SST) is a unique hybrid role for stores and is intended as a key pipeline for future career-growth within Firestone Complete ...
    Suggested
    Daily paid
    Temporary work
    Local area
    Flexible hours

    Bridgestone Americas

    Wilmington, VT
    4 days ago
  • HARDY INDUSTRIES is looking for skilled technicians to join their team in Wilmington, Vermont. This position involves a variety of technical tasks including OS installations, structured cabling, and telecom work in different environments such as retail and medical. Applicants...
    Suggested
    Flexible hours

    Hardy Industries Inc

    Wilmington, VT
    4 days ago
  • Assistant Manager As a Dunkin' franchisee, we are committed to our employees as much as we are committed to our customers. We value hardworking and enthusiastic employees and we make it a priority to ensure their success. The Assistant Manager will be responsible...
    Suggested

    Dunkin'

    Wilmington, VT
    2 days ago
  • DESCRIPTION As a Dunkin' franchisee, we are committed to our employees as much as we are committed to our customers. We value hardworking and enthusiastic employees and we make it a priority to ensure their success. The Assistant Manager will be responsible for...
    Suggested

    Dunkin

    Wilmington, VT
    2 days ago
  • $20 - $23 per hour

    Childrens Center Attendant Date: Jul 14, 2026 Location: West Dover, VT, US Company: Mount Snow Shift Type: Winter Seasonal 2026/2027 Create Your Experience of a Lifetime! Come work and play in the mountains! Whether it's your first-time seeing snow or you were born ...
    Full time
    Part time
    Seasonal work
    Local area
    Shift work

    Vail Resorts

    West Dover, VT
    2 days ago
  • $20 per hour

    Tune Shop Service TechnicianCreate Your Experience of a Lifetime! Come work and play in the mountains! Whether it's your first-time seeing snow or you were born on the slopes, joining our team means discovering (or re-discovering!) a passion for the outdoors while building...
    Seasonal work
    Flexible hours
    Shift work

    Vail Resorts

    East Dover, VT
    1 day ago
  • $25.25 per hour

    Salary: $25.25/Hourly Company Summary EchoStar is reimagining the future of connectivity. Our business reach spans satellite television service, live-streaming and on-demand programming, smart home installation services, mobile plans and products. Today, our ...
    Hourly pay
    Local area
    Flexible hours
    Afternoon shift

    EchoStar

    West Wardsboro, VT
    5 days ago
  • $50k - $65k

    Manager TraineeStewart's Shops is a fast growing convenience store chain in New York and Vermont with friendly store associates and great customers! We are looking for manager trainees to join our fast track training program in our shops. Our manager trainees work closely...
    Full time
    Traineeship
    Flexible hours

    Stewart's Shops

    Wilmington, VT
    4 days ago
  • Job Summary: The Crusher Plant Maintenance Operator is responsible for the safe and efficient operation, inspection, maintenance, and repair of crushing, screening, conveying, and related aggregate processing equipment. The position monitors plant performance and ...

    Peckham Industries

    West Halifax, VT
    3 days ago
  • $20 per hour

    Activities Attendant Date: Jul 14, 2026 Location: West Dover, VT, US Company: Mount Snow Shift Type: Winter Seasonal 2026/2027 Create Your Experience of a Lifetime! Come work and play in the mountains! Whether it's your first-time seeing snow or you were born on the...
    Full time
    Part time
    Seasonal work
    Local area
    Flexible hours
    Shift work

    Vail Resorts

    West Dover, VT
    2 days ago
  • $20 - $23 per hour

    HousepersonCreate Your Experience of a Lifetime! Come work and play in the mountains! Whether it's your first-time seeing snow or you were born on the slopes, joining our team means discovering (or re-discovering!) a passion for the outdoors while building lifelong connections...
    Full time
    Part time
    Seasonal work
    Work at office
    Local area
    Immediate start
    Shift work

    Vail Resorts

    East Dover, VT
    1 day ago
  • Why Dunkin’? America runs on Dunkin’, and so do our teams! We’re seeking motivated, energetic, and reliable individuals to join our team as Shift Managers . This is your opportunity to lead the way - ignite teams, wow guests, and level up your career! Perks & Benefits:...
    Flexible hours
    Shift work
    Afternoon shift
    Early shift

    Ontario Trillium Foundation

    Wilmington, VT
    2 days ago
  • $20 per hour

    Job Description Job Description Garde Manger for Award-Winning Restaurant Location: Southern Vermont (Ski Region) Position: Garde Manger (Cold Station / Pantry Chef) - Cross-training available Compensation: $20.00 / hour (Plus end-of-season bonus potential...
    Extra income
    Part time
    Local area
    Shift work
    Night shift
    Weekend work
    Afternoon shift

    Gecko Hospitality

    Wilmington, VT
    26 days ago
  • $22 per hour

     ...Housing Availability: No Job Responsibilities: ~ Clean guest units, offices, and common areas (including restrooms) at the property ensuring adherence to Vail Resorts quality, health, and safety standards ~ Replenish amenities in areas including, but not limited... 
    Full time
    Part time
    Seasonal work
    Local area
    Flexible hours
    Shift work
    Night shift
    Weekend work

    Vail Resorts

    West Dover, VT
    4 days ago
  • Job Description A Day in the Life: Our sales and store support teams, also known as clerks in the grocery world, play an important part in ensuring our stores are clean, organized, and shoppable so that our customers can find exactly what they need to keep their...
    Weekly pay
    Minimum wage
    Local area
    Flexible hours

    Albertsons

    Wilmington, VT
    3 days ago
  • Restaurant Manager As a Dunkin' franchisee, we are committed to our employees as much as we are committed to our customers. We value hardworking and enthusiastic employees and we make it a priority to ensure their success. The Restaurant Manager will always maintain...

    Dunkin'

    Wilmington, VT
    2 days ago
  • Job Title: Senior Software Developer Location: Client US DE Wilmington Years of Experience: 7 10 Years Job Summary: We are seeking a highly skilled Senior Software Developer with a strong background in AWS Administration to join our dynamic team. The ideal ...

    Yantran LLC

    Wilmington, VT
    1 day ago
  • DESCRIPTION As a Dunkin' franchisee, we are committed to our employees as much as we are committed to our customers. We value hardworking and enthusiastic employees and we make it a priority to ensure their success. The Restaurant Manager will always maintain a...

    Dunkin

    Wilmington, VT
    5 days ago
  • About the Role and Job: Job Title Service Management Lead Location: Wilmington, DE Model: Onsite Job Type : Full time/ Contract Job Summary: This job posting is for an existing, active vacancy and We are currently looking for ITIL Process...
    Full time
    Contract work
    Work at office

    Yantran LLC

    Wilmington, VT
    5 days ago
  • Note : This is an educational program, not a job. Successful completion of the program does not guarantee employment but will equip you with valuable skills for the healthcare job market. Looking to start a rewarding career path in the healthcare industry? Use Dreambound...
    Flexible hours

    Dreambound

    Jacksonville, VT
    19 hours ago
  • $22 - $26.88 per hour

    Create Your Experience of a Lifetime! Come work and play in the mountains! Whether it’s your first-time seeing snow or you were born on the slopes, joining our team means discovering (or re-discovering!) a passion for the outdoors while building lifelong connections ...
    Full time
    Part time
    Seasonal work
    Local area
    Shift work
    Afternoon shift

    Vail Resorts

    West Dover, VT
    5 days ago
  • Job Description Job Description Benefits: Flexible schedule Opportunity for advancement Profit sharing This Is Not Your Average Tech Job Are you a hands-on I.T. or Telecom professional looking for something beyond the desk? AMG Tech Support is seeking...
    Hourly pay
    For contractors
    Immediate start
    Flexible hours

    HARDY INDUSTRIES

    Wilmington, VT
    15 days ago
  • Description: Why join UCS? Since 1958, United Counseling Service (UCS) has been dedicated to providing exceptional care and support to individuals and families in our community. Through a wide range of programs, services, and educational opportunities, we strive to...
    Hourly pay
    Temporary work
    Work at office

    United Counseling Service of Bennington County Inc

    Wilmington, VT
    3 days ago
  • $55k - $65k

     ...locations. What You Bring: Minimum of 5 years of prior experience in the insurance industry, specifically within Personal Lines An active Property & Casualty License A strong sense of integrity, professionalism, and reliability A team-oriented mindset paired with high self‑... 
    Temporary work
    Internship
    Local area
    Remote work
    Flexible hours

    IMA Financial Group

    Wilmington, VT
    4 days ago
  • $20 - $30 per hour

     ...Little Bit About Us 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... 
    Hourly pay
    Local area
    Flexible hours
    Afternoon shift
    Early shift

    First Chair Destinations

    Wilmington, VT
    4 days ago
  • $69k

    Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely, serving clients by providing guidance and protection solutions...
    Remote work
    Work from home
    Flexible hours

    HMG Careers

    Whitingham, VT
    4 days ago
  • $20 per hour

    Create Your Experience of a Lifetime! Come work and play in the mountains!  Whether it’s your first-time seeing snow or you were born on the slopes, joining our team means discovering (or re-discovering!) a passion for the outdoors while building lifelong connections...
    Full time
    Part time
    Seasonal work
    Local area
    Flexible hours
    Shift work

    Vail Resorts

    West Dover, VT
    3 days ago
  • Job Description Job Description Position Purpose: The Account Executive is responsible for the overall sales execution of business objectives within their assigned territory by adding new business through efficient prospecting and account acquisition, retaining existing...
    For contractors
    Work at office
    Local area
    Flexible hours
    Night shift
    Weekend work

    Cal-Tex Protective Coatings Inc

    Wilmington, VT
    21 days ago
  • $27 - $32.14 per hour

    Create Your Experience of a Lifetime! Come work and play in the mountains!  Whether it’s your first-time seeing snow or you were born on the slopes, joining our team means discovering (or re-discovering!) a passion for the outdoors while building lifelong connections...
    Hourly pay
    Full time
    Seasonal work
    Local area
    Shift work
    Day shift

    Vail Resorts

    West Dover, VT
    21 days ago

Do you want to receive more vacancies?

Subscribe and receive similar vacancies to Property Caretaker. Be the first to apply!