Top 87 Server Jobs in Windham Me

FT/PT Front of House Restaurant Help - Chebeague Island Inn
Prentice Organization —Chebeague Island, ME
- Weekends as needed
- Bar
- Hotel
- Reliable transportation
Quick Apply
Server
Sicilian Table —Falmouth, ME
- $7.55 an hour + tips
- Part-time
- Customer service
- Mid-level
- In-person
- Free parking
- Paid time off
Quick Apply
Front of House Employee
Tuscan Brick Oven Bistro —Freeport, ME
- From $7.55 an hour + tips
- Part-time
- Mid-level
- In-person
- Restaurant
- Paid training
- Employee discount
Quick Apply
Part-Time Tasting Room Associate- Westbrook
Mast Landing Brewing Company —Westbrook, ME
- From $10 an hour + tips
- Part-time
- Bar
- Computer literacy
- Basic math
- Paid time off
- Employee discount
Quick Apply
Part-Time Taproom Server- Freeport
Mast Landing Brewing Company —Freeport, ME
- From $10 an hour + tips
- Part-time
- Serving
- Bar
- Customer service
- Paid time off
- Employee discount
Quick Apply
Server/Waitstaff at Black Cow Burgers & Fries
Black Cow Burgers & Fries —Portland, ME
- $20 - $30 an hour
- Serving
- Entry level
- Under 1 year
Quick Apply
Front of House Employee
Tuscan Table —South Portland, ME
- $7.55 - $10.00 an hour + tips
- Part-time
- Mid-level
- In-person
- Restaurant
- Paid time off
- Employee discount
Quick Apply
Portland Country Club Hospitality Team, Full Time
Portland Country Club —Falmouth, ME
- $21 - $23 an hour
- Weekends as needed
- Background check
- Serving
- Hospitality
- Paid training
- Paid holidays
Quick Apply
Catering Server - Per Diem
Bird & Co. —Portland, ME
- 12 hour shift
- Serving
- Casual dining restaurant
- Customer service
- Flexible schedule
Quick Apply
Server
Gorham House —Gorham, ME
- $17 - $20 an hour
- Full-time
- No experience needed
- English
- Computer skills
- Disability insurance
- Dental insurance
Quick Apply
Server Full-Time $500 Sign On Bonus
Stroudwater Lodge —Westbrook, ME
- Full-time
- Criminal background check
- Entry level
- Kitchen
- Paid holidays
- 401(k) matching
Quick Apply
3d
Server
Inn By the Sea —Cape Elizabeth, ME
- Full-time
- Restaurant
- Entry level
- Health savings account
- Paid holidays
Quick Apply
3d
Breakfast Server - Portland Sheraton at Sable Oaks
Colwen Management Inc —South Portland, ME
- Weekends as needed
- 18 years or older
- Hotel
- High school diploma or GED
- Health insurance
- Dental insurance
Quick Apply
4d
Server
The Foreside Tavern & side bar —Falmouth, ME
- $23 - $28 an hour
- Part-time
- Customer service
- In-person
- Restaurant experience
Quick Apply
3d
Server
Applebee's —Windham, ME
- $7.55 an hour
- Serving
- 18 years or older
- Casual dining restaurant
- Health insurance
- Flexible schedule
Quick Apply
Server - Weekends ONLY
The Friendly Toast —Portland, ME
- Weekends only
- Bar
- 18 years or older
- Computer skills
- Health insurance
- Dental insurance
Quick Apply
Food Server
AnJon's Ristorante —Scarborough, ME
- $23.03 - $50.03 an hour
- Part-time
- Background check
- Basic math
- Fair chance
- Employee discount
- Flexible schedule
Quick Apply
Server/Bartender
Big Bites Big Shots Inc —Old Orchard Beach, ME
- $25 - $50 an hour
- Weekends as needed
- Serving
- Bar
- Customer service
Quick Apply
14d
Server
Black Point Inn —Scarborough, ME
- Part-time
- English
- US work authorization
- Restaurant
Quick Apply
5d
Server (Shaking Crab Cajun Seafood House)
Shaking Crab Cajun Seafood House —South Portland, ME
- $8 - $40 an hour + tips
- Part-time
- In-person
- Restaurant
- Entry level
- Employee discount
Quick Apply
7d

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FT/PT Front of House Restaurant Help - Chebeague Island Inn

Prentice Organization
Chebeague Island, ME

Quick Apply

Job Details

Seasonal

Qualifications

Customer communication

Full Job Description

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 part-time Front of the House Restaurant Help to join our seasonal team. In this role, you will play a vital part in the day-to-day operations of the restaurant from serving, bartending, hosting, and overall support. Candidates should be aware specific responsibilities could change daily, depending on operations.

These are full-time/part-time seasonal roles starting early mid-May to early 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
Flex between front-of-house roles as needed, including serving, bartending, hosting, and general support
Greet and seat guests, manage reservations and waitlists, and maintain a smooth and thoughtful flow of service
Take food and beverage orders with care and attention to detail, ensuring accuracy and pacing
Prepare and serve beverages in accordance with Inn standards, emphasizing quality and consistency
Run food, clear and reset tables, and support team members to ensure seamless service throughout each shift
Maintain cleanliness and organization of dining areas, bar, and service stations
Communicate clearly and effectively with kitchen and front-of-house teams to support a cohesive guest experience
Anticipate guest needs and respond promptly with professionalism and care
Uphold all health, safety, and alcohol service standards
Contribute to a positive, team-oriented environment and adapt to the dynamic needs of a seasonal inn

Qualifications

Previous hospitality experience preferred (serving, bartending, hosting, or support roles)
Strong communication and interpersonal skills
Positive attitude with a team-first mindset
Ability to adapt and work in a fast-paced, dynamic environment
Strong attention to detail and commitment to guest experience
Reliable, punctual, and professional in appearance and demeanor
Willingness to learn and take on multiple responsibilities
Ability to work evenings, weekends, and holidays during the season

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!

Quick Apply

Refine Your Search

server jobs in windham me

FT/PT Front of House Restaurant Help - Chebeague Island Inn

Server

Front of House Employee

Part-Time Tasting Room Associate- Westbrook

Part-Time Taproom Server- Freeport

Server/Waitstaff at Black Cow Burgers & Fries

Front of House Employee

Portland Country Club Hospitality Team, Full Time

Catering Server - Per Diem

Server

Server Full-Time $500 Sign On Bonus

Server

Breakfast Server - Portland Sheraton at Sable Oaks

Server

Server

Server - Weekends ONLY

Food Server

Server/Bartender

Server

Server (Shaking Crab Cajun Seafood House)

I want to receive the latest job alert for server in windham me

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