Oakland House Cottages by the Side of the Sea & Hostel@Acorn by the Sea

Live & Work Seaside on the Maine Coast

Oakland House is a family owned and operated oceanfront cottage colony. It offers 10 sophisticatedly rustic 1- & 2-bedroom cottages plus 6 rooms in the "no frills/budget-wise" hostel. The land it is on has been in the same family since 1767. There is a recreation barn for special events. It has been welcoming guests since 1889 and retains its relaxing, welcoming, old-fashioned charm.

Oakland House is located centrally on the Blue Hill Peninsula on the shore of Eggemoggin Reach magically facing the setting sun and the islands of East Penobscot Bay. There are 60 unspoiled acres, several shorefront beaches, hiking trails, lookouts and play lawns - a natural oasis of authentic old Maine!

About Oakland House Cottages by the Side of the Sea

Although the cottages vary in age between 40 and 120 years old, they exude a sophisticated rusticity uncommon in today's world. They vary in style and appointments greatly. Each is a treasure: fun and inviting. Oakland House's primary goal is to provide a friendly and welcoming environment in which the staff strives to provide friendly and attentive service without appearing hectic, which is sometimes the case.

We are seeking strongly motivated individuals with excellent hospitality skills and an ease being with people. No matter what your position, hospitality is important. We often ask employees to wear different hats as the need arises. Our family oriented resort requires cheerfulness and a neat appearance.

Check out our Oakland House and Hostel@Acorn Facebook pages for more photos.

The Employee Experience

It is our objective to provide a fun and memorable experience for our employees. Working hours are generally about 40 hours per week with two days off each week. We make every attempt to give consecutive days off, however seldom two weekend days in a row. Occasionally, staff members are called on to work overtime. But, that is not the norm. Hours over 40/week are paid time and a half.

It is mandatory to have a vehicle to drive when you come. While we are not far from Blue Hill (11 miles) you will want to have the flexibility to drive to buy groceries and to spend free time exploring the many offerings of the Blue Hill Peninsula. Bar Harbor and Acadia National Park is about an hour's drive away. Mount Katadin is about a 3 hour drive. Mount Katadin is the end of the Appalacian Trail. There is a very sophisticated well marked trail system on the Blue Hill Peninsula at Blue Hill Heritage Trust.

Each staff member will have a private room. The bathrooms are shared as is the large kitchen, living areas and screened porch. There is a staff laundry in the staff residence building that is FREE to use.

While we work hard, we also have a lot of fun.

Ideal Candidate

We have many requests for seasonal employment at Oakland House. Since our season continues into the fall we must evaluate an applicant's availability as we go through the hiring process. Our staffing requirements do drop in early September so although we can overlap staff throughout the season, the longer an applicant is able to stay, the more likely we are to hire. We are seeking individuals who are interested in coming back season after season.

Since our goal is to provide cheerful, excellent service to our guests we hire individuals who are friendly, neat, and take pride and pleasure in serving our guests.

Room and Board

Local housing rentals tend to be extremely high due to the high desirability of accommodations during the season. We provide on-site housing with individual rooms and shared bathrooms. We provide staff linens and blankets. There is a community kitchen as well. Employees are responsible for their own food.

We welcome your overnight guests (if space allows) with prior notice and a $5/night fee. Quiet hours are to be observed from 10:30 PM until 7:00 A.M.

Employee Perks


Compensation is based upon experience and can vary. All employees are required to be able to work the hours necessary for their job description. In this hospitality business it may be required that an employee work a split shift (i.e. working in the early hours in the laundry, taking a break and then returning to work in the office, or a rotating shift with changing hours.

Each department operates on a time schedule that directly relates to the needed tasks for that week.

All wages are before State and federal withholding tax, social security, and Medicare. While guests may leave tips, this is not a tip-based wage. We practice a "tip pooling" policy as we act as a team. Reporting of tips may be required by the employee.

Our payroll is done by automatic deposit so we ask for a cancelled check from your account prior to your first week's pay.

Getting Here and Getting Around

HOW DO I GET AROUND? It is definitely best if you have your own vehicle. The closest town with full amenities is Blue Hill which is about fifteen minutes by car. Our website has detailed driving directions to get here from just about anywhere! The country store is within about a 20 minute walking distance (3 miles). A bicycle is very useful transportation. A kayak will provide hours of pleasure if you bring one.

For Fun

The Blue Hill area is rich in culture and the arts (music, art galleries, pottery shops, libraries, etc.) and opportunities for outdoor recreation in a stunning environment (nature preserves, hiking, sunbathing, swimming, ocean going boating, and lake fishing, kayaking, etc.). We have beautiful hiking trails through the complex. And, it’s a terrific place to kayak. More nearby towns are Stonington, Castine, Ellsworth, and Bar Harbor (Acadia National Park) which are between a half-hour and an hour drive away.

Our Jobs

We have administrative jobs, guest service and customer service position positions, housekeeping jobs and groundskeeping and maintenance jobs. Please see the job list on our website for more detailed job descriptions and specific season dates for each position.

Note: Qualifications for our Office/Reservations Agent position must be comfortable working on a PC and be proficient in MS Word and MS Excel. We will train you to use our online reservation system (ResNexus). If you have used it already, so much the better. If you are a "people person" as well we would love to talk with you. This will be a key position in 2017.

Housekeeping/Laundry Staff


(3 required to arrive about June 3rd, depart in Aug. or Sept.) We will need several individuals to arrive and depart on a staggered schedule through the season. It's a great opportunity to meet our amazing guests and be a crucial part of our operations. Attention to detail is important as is a positive attitude and ability to be a team player and follow directions and procedures. You must have a cheerful willingness to chip in with other duties including laundry, cabin service, firewood delivery, and general hospitality. An ability to lift 40 lbs. on a periodic basis is necessary for this position.

Multi-tasker/painter/grounds/trail worker


One individual required. Flexible Arrival/Departure: Examples: arrive early May, depart mid-summer OR arrive mid-summer, depart end Oct. etc. We always have the need for exterior painting, grounds, trails and repairs. This is a perfect summer job for the right applicant who desires the opportunity to see the coast of Maine, wants FREE lodging, and is willing to chip in with other tasks as needed. The best applicant needs to have some real painting/prepping experience and must be able to work on their own. You must be fit and able to safely lift and move furniture and other equipment if needed. Come join our team for a few months when you are available.

How to Apply

The Apply Now button will lead you to our online application. If you'd rather print an application and mail or fax it to us, you can do so by clicking here.

NOTE: We can NOT provide assistance in obtaining visas. U.S. law mandates that we follow certain guidelines when we hire overseas applicants, and we adhere strictly to those guidelines. We are NOT actively seeking applicants with J-1 Visas since we cannot provide transportation as necessary to live here on site. Please save yourself the time by not applying.

Learn more about Hostel@Acorn.

Oakland House Cottages by the Side of the Sea and Hostel@Acorn by the Sea are a drug-free workplaces.