iTrip Annapolis
August 24, 2022
Annapolis, Maryland
Job Type
Annual Salary $30,000 - $50,000



Our beautiful city of Annapolis is home to incredible museums, historical attractions, the U.S. Naval Academy, and gorgeous ocean views. No wonder people come from all over the United States and the globe to vacation in this fascinating city.

 If you love history, and hospitality and have a lot of hustle, then you may be the exact person we’re searching for to step into this critical role as our Head of Housekeeping here at iTrip Annapolis.

iTrip Vacations was started in 2008 by vacation rental owners for vacation rental owners. The company has since grown into one of the top property management leaders in North America. Each iTrip Vacation destination is managed by a local team, available 24/7, who lives in the area. This, combined with state-of-the-art systems and proven processes, enables iTrip Vacations to provide boutique-level services backed by a national brand to all our short-term rental owners and guests.

As a team, we are committed to offering our guests incredible experiences and cultivating a work culture where our employees thrive. 


As our Head of Housekeeping, you’ll report directly to our Director of Operations and be responsible for managing all house cleaning-related duties at our 50+ short-term rental properties in and around Annapolis. This will include managing all communications with cleaning crews, scheduling cleaning crews for turnover cleanings, management of linen services, and tracking and maintaining each home’s inventory of consumables.

This is the perfect position for someone who embraces their need for perfection, employs high standards, and loves to share their deep knowledge of how to keep a home immaculate from top to bottom.


  • Work with cleaning crews to ensure all homes are clean before and after each guest's stay.
  • Create the scheduling for all cleaning and quality inspection crews based on bookings emailed through our online system.
  • Use our Resort Cleaning Software to schedule and manage cleanings and train team members on its use.
  • Ensure that all beds have fresh linens, enough towels and that enough consumables are stocked and ready for each stay.
  • Manage all communication with cleaning crews and quality inspection teams.
  • Report back to the Director of Operations to keep sharing any pertinent information about any scheduling or cleaning crew issues. 
  • Identify any issues at the homes that may need to be repaired/improved between guest stays.


  • Previous housekeeping experience in the vacation rental or hospitality industry.
  • You must be able to pass a background check.
  • Access to reliable transportation and  a valid Driver’s License with a clean record
  • Extremely task-oriented with high standards for quality and accuracy.
  • Proficient in using phone apps and computers.
  • Regular work hours with a willingness to work on weekends.


Annual Salary: $30,000 - $50,000

Hiring Note- You must be able to pass a background check,  have a clean driving record, and have access to reliable transportation.


  • Workplace perks such as recreation activities, food and coffee, and a flexible work schedule