Lead a Dynamic Housekeeping Team in a Beachside Resort Near Chicago - Seasonal or Year Round Options

The Wanderluxe Collection is seeking a Director of Housekeeping to lead housekeeping and laundry operations across more than 150 vacation homes in Northwest Indiana and Southwest Michigan. This is a year-round, full-time leadership role based at our flagship property, Beachwalk Resort, a vibrant, storybook lakeside community just steps from Lake Michigan. Though we are hoping to find the perfect person to join our operation full time, we are also open to Summer Seasonal managers with experience.

We’re a growing hospitality company managing a diverse portfolio of vacation rentals, united by a shared commitment to exceptional cleanliness, service, and unforgettable guest experiences. As Director of Housekeeping, you’ll play a key role in shaping both team culture and guest satisfaction across multiple properties.

What You’ll Do

You’ll recruit, train, and inspire a large housekeeping and laundry team, scaling up to 100 seasonal team members in peak summer months. You’ll oversee daily operations, inspections, inventory, scheduling, and cost control while refining systems and procedures that keep everything running smoothly. This is a hands-on role for a leader who isn’t afraid to roll up their sleeves and lead by example.

You’ll collaborate closely with other departments, homeowners, and vendors, contribute to budgeting and forecasting, and ensure brand standards are met across all locations.

Who Thrives Here

This role is perfect for a hospitality leader with experience in hotels, resorts, or vacation rentals, especially multi-site or high-volume operations. You’re organized, people-first, tech-savvy, and energized by fast-paced environments. You know how to motivate teams, solve problems on the fly, and create a culture where people take pride in their work.

Why You’ll Love It

• Full-time, year-round leadership position OR Summer Seasonal (April through September). If applying for and selected for a seasonal management role, housing will be provided, and annual salary will be prorated. 

• Low-cost health clinic access

• Medical, dental, vision (after 31 days) for year-round team members

• 401(k) after one year for year-round team members

• Opportunities to grow with a rapidly expanding hospitality company

• A workplace that feels more like a family than a corporation

• Live and work in a charming beach town just one hour from Chicago, with over $500M in new investment transforming the area

You’ll report directly to our Vice President of Hospitality and have a meaningful voice in how we grow.

If you’re passionate about people, quality, and creating exceptional stays in a beautiful lakeside setting, we’d love to meet you. Apply today and help us make every stay unforgettable.