Job Summary
We are looking for a Maintenance Lead to take full ownership of the maintenance, repairs, inspections, and upkeep across several boutique short-term rental properties in the Shawangunk Ridge area. Must be located within 10 miles from Kerhonkson, NY area.
This is a hands-on, multi-skill role for someone who thrives on responsibility, stays organized, and takes pride in doing work the right way.

You will be trained directly by the owner, but the long-term expectation is independence, strong decision-making, and consistent high-quality execution.
The ideal candidate is a self-starter, a true jack-of-all-trades, and someone who enjoys solving problems, staying organized, and keeping properties running at a boutique-level standard.

Experience in roles such as building superintendent, multi-property maintenance technician, hotel/hospitality maintenance, facilities technician, or field service operations is highly valuable.
These backgrounds typically involve independent problem-solving, managing repairs across multiple locations, organizing tools and materials, communicating with stakeholders, and maintaining professional-grade standards — all essential components of this position.

If you enjoy working with your hands, staying busy, organizing tools and systems, and taking full ownership of your craft, this is an excellent opportunity to grow into a key leadership role in an expanding hospitality operation.

Responsibilities :

Daily / Ongoing Maintenance

Perform repairs, troubleshooting, and general upkeep across multiple properties.
Handle minor and major tasks including carpentry, plumbing, electrical, HVAC basics, painting, furniture fixes, and structural improvements.
Conduct regular property inspections and document new issues immediately.

Planning, Organization & Documentation

Maintain detailed notes in shared Excel tables (Fix & Improve, Payment spreadsheet, appliance tracking, etc.).
Track models of appliances, tools, and equipment for future servicing or replacement.
Prepare accurate end-of-day reports with hours, photos, and notes.
Preplan materials and tools needed for upcoming jobs to avoid delays.

Coordination & Communication

Stay in close communication with the Operator and caretaking team.
Respond promptly during working hours — priorities can shift quickly.
Attend weekly coordination meetings to plan the week’s work and review priorities.

Quality & Hospitality

Complete all work to a “bulletproof and dumb-proof” standard — durable, solid, and built to last.
Finish each task cleanly and professionally to match boutique property standards.
Follow “Leave No Trace” cleanup rules after each job.

Operational Responsibilities

Organize and maintain all tools, materials, and machinery.
Optimize driving routes and hardware store trips.
Perform occasional physical labor, cleanup, or staging as needed.
Take ownership of the maintenance function and support the smooth operation of the entire STR portfolio.

Skills

Technical Skills
Broad handyman skill set: carpentry, minor electrical, plumbing, HVAC basics, drywall, painting, troubleshooting.

Organizational Skills

Excellent note-taking and documentation habits.
Ability to track materials, tools, model numbers, and job details.
Strong time-management and planning skills.
Comfortable working across multiple properties with shifting schedules.

Communication & Mindset

Immediate responsiveness during work hours.
Clear, concise communication — focused on solutions.
Ability to work independently without needing constant direction.
Ownership mentality — treats properties and tools with care.
Positive, respectful attitude around guests, team members, and neighbors.

Personal Attributes

Self-starter who enjoys responsibility.
Not afraid to take on any task: big, small, physical, technical, or aesthetic.
Calm under pressure and flexible when priorities shift.
Strong integrity and honesty — especially in logging time and expenses.

Requirements

Valid driver’s license and reliable transportation.
Ability to lift 50 lbs, navigate stairs, and work indoors/outdoors.
Availability between 11 a.m.–4 p.m. (turnover window), with flexibility for early/late projects.
Ability to diagnose issues, research solutions, and execute repairs.
Comfortable using power tools, ladders, and equipment safely.

Job Types: Full-time, Contract

Pay: $27.00 - $37.00 per hour

Expected hours: 15 – 50 per week

Benefits:

Flexible schedule

Application Question(s):

Describe you current skills which matches job requirement

Location:

Kerhonkson, NY 12446 (Required)

Work Location: In person

Dream House in the Gunks

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Maintenance Lead – Short-Term Rental Properties