Skiing Big Sky and Lone Peak on the Employee Ski Pass

Live where others only get to Vacation.

Posted: Oct 08, 2026

Property Maintenance

Two Pines Properties

Big Sky, Montana

Wages/Pay
$25.00 - $30.00 / hour
Experience Level
Some experience required
Job Start Date
Nov 01, 2026

Pay: $25.00 - $28.00 per hour
Job description:
About us:
At Two Pines, we're more than just a vacation rental company, we’re a close-knit team of passionate professionals who are dedicated to delivering exceptional experiences to our guests and homeowners. As the largest locally owned and operated vacation rental company in Big Sky, we pride ourselves on creating a positive impact on our community, and we’re looking for like-minded individuals to join us.
We offer a dynamic, fun, and supportive work environment where you’ll not only contribute to our company’s growth but also thrive in a place that offers an unparalleled work-life balance. From skiing and hiking in the winter and summer, to building lasting relationships within our team and with our guests, working at Two Pines Properties means living and working in one of the most exciting resort towns in the country.
Position Overview:
The Property Maintenance & Repair position will be responsible for the upkeep and repair of our high-end vacation rental properties. You’ll handle various maintenance tasks independently, including plumbing, electrical, drywall repair, appliance repair, and more. You’ll also be expected to manage your time effectively, using company-approved software on your personal phone to track and complete tasks.
Key Responsibilities:

  • Plumbing: Repair, replace, or install faucets, pipes, toilets, dishwashers, and more.

  • Electrical: Repair, replace, or install switches, fuses, outlets, ceiling lights/fans, and climate control systems.

  • Drywall Repair: Patch holes or damage from normal wear, tear, or guest-related issues.

  • Appliance Repair: Repair or replace household appliances such as refrigerators, dishwashers, and dryers.

  • Carpentry: Adjust or repair cabinet fixtures, doors, windows, etc.

  • Snow Removal: Assist with maintaining walkways and driveways in the winter by shoveling snow.

  • Customer Service: Communicate professionally with guests, owners, and contractors regarding maintenance services.

  • Time Management: Track and complete maintenance tasks efficiently using maintenance software on your personal phone.

Compensation:
Starting hourly wage of $25 to $29 per hour, based on experience, with approximately 40 hours per week.
Benefits:

  • PTO: 120 hours, with increasing allowances based on years of service.

  • Health Plan: BlueCrossBlueShield medical plans, with Two Pines contributing 75% of the premium for the Bronze plan.

  • 401k: Eligible after 6 months, with a 4% match.

  • Ski Pass: Full-time in-person employees are eligible for a ski pass to Big Sky Resort (50% employee contribution, reimbursed at the end of the season).

Employee Housing:
We offer affordable employee housing options in well-maintained homes, townhouses, or condos. You will have your own private bedroom, while sharing common areas such as the kitchen and bathroom with fellow employees. The monthly housing cost is affordable, and more details about availability and pricing are provided upon request.
Conditions of Employment:

  • Must pass a background check and motor vehicle record check.

  • Must have a clean driving record of a minimum of 3 years, and hold a valid license. This must be maintained during employment.

  • Sign a non-compete and non-disclosure agreement.

  • Work weekends / holidays if needed.

Job Type: Full-time
Benefits:

  • 401(k)

  • 401(k) matching

  • Dental insurance

  • Flexible schedule

  • Health insurance

  • Paid time off

  • Vision insurance

License/Certification:

  • Driver's License (Required)

Ability to Relocate:

  • Big Sky, MT: Relocate before starting work (Required)

Work Location: In person

How to Apply

Contact Info

Two Pines Properties

We’re all about keeping it local, real, and rooted in Big Sky. As the largest locally owned vacation rental company, we take pride in smooth guest stays and a team that feels like friends. Trust, teamwork, and good vibes guide us. If you want your work to matter and love the mountain life, you’re home.

Location
Montana
Season
Spring, Summer, Fall, and Winter
Staff size
20-30
Housing
Whether included in the compensation package or provided at a cost, housing is provided for staff.
Housing details
Housing in Big Sky! 10 minutes to Biggest Skiing in America. Double occupancy housing available in a beautiful home in Big Sky, MT. Please inquire about more
Family housing available
No
Single occupancy housing available
No
Pet friendly
No
Meals
None
Cell phone service
Yes, most carriers
Internet access
Good
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