About Chebeague Island Inn
Nestled on 2.5 acres of breathtaking oceanfront property, Chebeague Island Inn, part of the Prentice Hospitality Group portfolio, offers panoramic views of Casco Bay with golden sunrises and spectacular sunsets. Just 20 minutes north of Portland, our 21-room boutique hotel provides an intimate, tranquil escape — where serene rooms, free of TVs and phones, invite guests to slow down and savor coastal living. From weddings to weekend getaways, the Inn is a cherished retreat, blending classic New England charm with warm, personalized service.
Position Summary
We are seeking seasonal Supervisors to support daily operations across our restaurant, food and beverage, and Inn programs. This role works closely with the management team, helping to execute service standards, support the team, and ensure an exceptional guest experience.
The ideal candidate is an enthusiastic, hands-on hospitality professional who leads by example, communicates clearly, and takes pride in delivering outstanding service in a one-of-a-kind island setting.
These are seasonal roles starting now and ending in October (exact dates may vary). The candidate will need to have reliable transportation to and from Chebeague Island Inn or find housing on the Island.
Key Responsibilities
- Deliver warm, genuine hospitality to all guests, creating a welcoming and memorable island experience
- Support restaurant and food & beverage operations during assigned shifts.
- Assist in overseeing daily Inn operations as directed by management.
- Help onboard, coach, and motivate team members.
- Uphold guest satisfaction and service standards on the floor.
- Assist with labor tracking, opening/closing duties, and operational checklists.
- Maintain cleanliness, safety, and compliance standards.
- Contribute to a positive, team-oriented, hospitality-driven culture.
Qualifications
- Experience in a supervisory or lead role in restaurants, hotels, or hospitality.
- Strong communication and team-support skills.
- Comfortable working in a hands-on, fast-paced environment.
- Reliable, organized, and guest-focused.
- Eagerness to learn and grow within a leadership track.
What We Offer
- Competitive hourly pay
- Seasonal employment in a beautiful island setting
- Opportunities for growth within Prentice Hospitality Group
- Supportive, team-oriented work environment
Why Join Us
At PHG, our work is guided by three core pillars: A Culinary Lens, Modern Service with Classic Values, and A Sense of Place. Food is our anchor — rooted in the terroir of Maine and executed with intention, discipline, and respect for craft. We deliver hospitality that is best in class, relationship-driven, and grounded in professionalism and care.
Our values — Expert, Nimble, Ambitious, Inclusive, and Timeless — shape how we operate every day. We bring deep expertise to our craft, move with agility, strive for excellence, foster welcoming environments for all, and build concepts designed to endure. Each of our restaurants is connected to its neighborhood and community, contributing meaningfully to Maine’s evolving hospitality landscape while creating lasting value for our guests and our teams.
We’re excited to meet passionate, dedicated individuals who want to grow with us. Apply today and become part of our amazing team!
Skills Required
- Experience in a supervisory or lead role in restaurants, hotels, or hospitality.
- Strong communication and team-support skills.
- Comfortable working in a hands-on, fast-paced environment.
- Reliable, organized, and guest-focused.
- Willingness to assist with labor tracking, opening/closing duties, and operational checklists.
- Availability for a seasonal role (now through October, dates may vary).
- Reliable transportation to/from Chebeague Island or ability to secure housing on the island.
- Eagerness to learn and grow within a leadership track.
What We Do
The Prentice Organization is a privately held investment and development company based in Maine. The company focuses on hospitality management, real estate investment, real estate development, and real estate asset management. Its diverse portfolio spans a wide range of asset types, demonstrating the depth of its team's expertise in creating thoughtful hospitality experiences and community-driven real estate projects throughout the Northeast.
