Join Our Team
See all the opportunities available to join the InnSeason Family
Experience the InnSeason Difference
At InnSeason Resorts, we aim to live our vision statement out loud with every customer and every team member, every day. Simply stated, we strive to set the standard for ingenuity and excellence within our industry and community in all that we do – one experience at a time. If you feel that this describes who you are and the culture you want to not only be a part of but truly impact, we want to hear from you.
3 Ways to Get Started
Apply now or contact us.
If you have a resume with work history and references. Complete this short form and attach your resume.
If you don't have a resume. Complete this online application with your work history and references.
If you have a question before you fill out an application, reach out to us, we would love to speak with you!
Find your fit
As one of North America's largest independent vacation ownership developers, we have opportunities throughout New England, in some of the most beautiful tourism destinations in the northeast. Whether you are looking to start or change careers in sales, hospitality, maintenance, or administration, we are always looking for talented, passionate individuals to join our family.
Check out our current positions below
Massachusetts Positions
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Administrative Assistant II - InnSeason Resorts Harborwalk Sales - Falmouth, MA
Job description
Come join our team and love where you work! InnSeason Resorts Harborwalk Sales office seeks a Sales Administrative Assistant II responsible for supporting the sales process by ensuring that all Company policies and procedures are adhered to in the Tour Registration and contract office, in compliance with Company Brand Standards. This is a great fit for someone who has attention to detail, is organized and has strong customer service skills. You have a four day work week with this position--Friday-Monday, weekly, including holidays.
Responsibilities include greeting and registering tours in a professional manner, contract preparation and processing, ensuring integrity of tour and transaction data, deposits and reconciliation, ordering and accounting for premium and sales materials inventories and ensuring the assets of the Company – its people, property, customers and data - are preserved.
Key Responsibilities- Implement and improve procedures for the efficient operation of the Contracts Office
- Efficiently provide tour registration, contract processing, and data review and reconciliation services to the Office
- Ensure that all tours are accounted for and dispositioned appropriately each business day
- Ensure that contract and customer data are entered uniformly and accurately
- Reconcile contract, customer and financial data each business day
- Account for and reconcile inventories of gifts, premiums, certificates and sales presentation and support materials
- Account for and reconcile the deposits for each of the day’s sales
- Daily communication of data, documentation and funds with Corporate Contracts Department
- Support timely response to customer inquiries
- Ensure that all daily, weekly and monthly Sales Office administrative processes are completed timely and accurately
- Deliver exceptional customer service to all internal and external customers
Qualifications
- Associate’s degree, preferred, but not necessary.
- 4-6 year’s relevant experience in Customer Service and Administrative processes.
- High proficiency in typing, computer systems and Microsoft Office Applications.
- Proven ability to multi-task and work well under deadlines.
- Demonstrated track record of integrity, professionalism, teamwork and customer service.
- Demonstrated ability to manage details and complexity.
Schedule: Friday, Saturday, Sunday and Monday-including most holidays that fall on those days.
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Appointment Setter - InnSeason Management, Inc. - Hyannis, MAAre you customer focused with exceptional phone skills? We would love to talk to you about an Appointment Setter position at our InnSeason Resorts Hyannis office! We’re currently looking to hire 2 part-time (15-25 hours/week) people to add to our team. Appointment Setters earn $15/hour plus bonuses on every booking.
InnSeason Resorts is the Northeast’s premier Vacation Ownership company and we are focused on giving our members an outstanding vacation experience! We also want them to make the most of the product they already own. In order to do that, our Appointment Setters contact existing members to set appointments for member workshops in order to get them vacationing more than ever! There is no selling involved.
We’d love for candidates to have telemarketing or call center experience, but we’re willing to train the right person. This makes a great secondary or primary job.
Responsibilities:
- Contact Owners for promotional updates at resort sales centers and Road Show.
- Assist in the presentation and distribution of marketing materials to be used in the marketing efforts for all InnSeason Resort properties and any affiliates.
- Assist in integrating various marketing activities, direct mail, social media and promotional campaigns that will result in qualified tours.
- Engage with customers in a professional and friendly manner, providing information about products and services
- Maintain accurate records of customer interactions and appointments scheduled
- Fluent in English with excellent verbal communication skills
- Previous experience in sales, customer service, or telemarketing is preferred
- Strong interpersonal skills with the ability to build rapport with customers over the phone
- Proficient in using software applications for data entry and customer relationship management
- Ability to negotiate and overcome objections to secure appointments
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Maintenance Technician - InnSeason Resorts - Falmouth, MA
Job Summary:
The Maintenance Tech 1 is expected to perform routine maintenance and repair duties for guest rooms, mechanical spaces, pool equipment, and any other basic areas on the property.
Essential Job Duties & Responsibilities:
- Complete special projects in a timely manner.
- Perform routine engineering duties as required.
- Ensure that room maintenance requests are handled in a prompt & courteous manner.
- Make basic repairs to units including, but not limited to, air conditioners, tiles, bathrooms, all fixtures, furniture, wall coverings, sheetrock, painting, and basic plumbing.
- Replace TV’s, VCR’s, DVD’s and program TV’s as required.
- Perform preventive maintenance in units and on equipment.
- Assist grounds personnel as directed. Use of lawn care equipment and snow removal equipment.
- Attend department and staff meetings as directed.
Skills Required:
- Knowledgeable use of hand & power tools, electrical test equipment, refrigeration equipment, plumbing tools & equipment, audio-visual equipment, telephone & telephone systems, office equipment, computer and computerized systems.
- Heavy work - exerting up to 100 lbs. of force occasionally.
- Must be able to convey information & ideas clearly.
- Must work well in stressful, high-pressure situations.
- Ability to work in all weather conditions.
- Must have and maintain a valid driver’s license.
Education / Experience:
- Trade school or related training helpful
- High School diploma or equivalent required
Expected Conduct:
- Set the standard for professional behavior at all times
- Be knowledgeable of, practice and reinforce good business practices relating to harassment, discrimination and hostile environments in the workplace
- Remain aware and compliant with company policy and government regulations in regards to employment practices, as communicated by the Human Resources Department
- Remain calm during stressful and hectic periods
- Arrive at and depart from work according to schedule, or as needs dictate
- Make arrangements for job duties to be fulfilled during periods when you will not be present
- Always present a positive attitude about the Company and co-workers
- Abide by the words and intent of the Company Credos.
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Sales Representative - InnSeason Resorts Harborwalk Sales Team - Falmouth, MA
Job description
InnSeason Resorts HarborWalk, on beautiful Falmouth Harbor overlooking the Nantucket Sound, seeks outgoing and upbeat individuals, with or without sales experience. We’re turning away business because we need more sales talent—could that be you? This is a great opportunity for someone who is looking for a more consistent and well-paying sales position or those who always thought they would be successful in the right sales environment. No sales experience required! We invest in you with top-notch training—just bring a can-do attitude! We’re turning away business because we need more sales talent—could that be you? This is a great opportunity for someone who is looking for a more consistent and well-paying sales position or those who always thought they would be successful in the right sales environment. No sales experience required! We invest in you with top-notch training—just bring a can-do attitude!
This position includes:- Competitive Pay Plan - Salary plus Commission (Sales Representative earn $15.00/hr. + commission)
- **$2,000 Sign On Bonus (conditions apply)**
- Opportunity to Earn a $100K Annual Income
- Supportive Management Staff
- Ongoing Training
- Year-Round Position
- Weekends Mandatory
- Weekly Cash Bonuses & Monthly Bonuses
- Fun Working Atmosphere
- Free or Discounted Resort Vacations for Employees
- Hours of Operation are typically Friday-Sunday, 8:30am-4:00pm, but change based on tour volume.
If you have felt you have not yet reached your full potential and want the opportunity to grow, InnSeason Resorts could be what you have been looking for! We have more customers than we can handle—are you ready to join our team and grow with us? -
Front Desk Agent - InnSeason Resorts Captain's Quarters - Falmouth, MA
InnSeason Resorts is seeking a dynamic and detailed individual for Front Desk Agent in Falmouth, Cape Cod at our Captain's Quarters resort. This is a full-time, year-round position. Pay range is $18-20 per hour, depending on experience and the schedule is a mix of day and evening shifts, Monday thru Sunday (weekend shifts required).
The main responsibilities of the Front Desk agent are positive guest interaction, check-ins and check-outs, assisting guests with their requests, handling the cash drawer, and operating a switchboard. We are looking for someone who is energetic, has a good attitude and likes to interact with people.
Applicants must be at least 18 years of age, as the duties and scheduling requirements of this position are not eligible for employment by minors under applicable law.
Skills Required
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Strong verbal and written communications skills
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Strong computer skills
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Attention to detail and the ability to multi-task.
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Strong Customer Service skills with and outgoing personality.
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Strong decision making skills with the ability to prioritize
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Must be flexible in scheduling (Weekends required)
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Must be able to stand or sit for long periods of time
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Ability to work regardless of weather conditions
Benefits for Full-time employees Include:
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Health insurance
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Employee & family lodging discounts
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Flexible schedule
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Dental insurance
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Life insurance
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Vision insurance
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Paid time off incl. vacation, personal & holiday pay
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Referral program
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Bereavement and jury duty pay
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Maine Positions
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Housekeeper - InnSeason Resorts The Falls at Ogunquit - Ogunquit, ME
Job Description
Candidates should have cleaning experience in hospitality or retail setting, able to work in a fast paced environment and having great customer service skills is a must. Excellent opportunity to join a great team with future opportunities for professional growth.
Essential Duties:
- Clean and restock rooms and carts following Standard Operating Procedures
- Communicate any necessary information to supervisor and staff relating to guest issues
- Keep linen storage rooms and supply closet clean and secure at all times
- Will be required to pitch in and help coworkers with their job duties
- Must be flexible and adaptable under changing conditions, priorities and unexpected situations
- Must be able to display a positive and enthusiastic attitude
Benefits Include:
- Employee & family lodging discounts
- Flexible schedule
- Paid time off incl. vacation, personal & holiday pay
- Referral program
- Short-term dissability
- Bereavement and jury duty pay
Job Type: Full-time and Part-time available
Pay: From $14.00-16.00 per hour
COVID-19 considerations:
Employees are required to wear masks while on the property, maintain social distancing, and follow company Covid-19 protocols. Surfaces are sanitized on a regular basis, and as needed. PPE is provided if needed. -
Maintenance Technician - InnSeason Resorts The Falls at Ogunquit - Ogunquit, ME
Job Summary:
The Maintenance Tech 1 is expected to perform routine maintenance and repair duties for guest rooms, mechanical spaces, pool equipment, and any other basic areas on the property.
Essential Job Duties & Responsibilities:- Complete special projects in a timely manner.
- Perform routine engineering duties as required.
- Ensure that room maintenance requests are handled in a prompt & courteous manner.
- Make basic repairs to units including, but not limited to, air conditioners, tiles, bathrooms, all fixtures, furniture, wall coverings, sheetrock, painting, and basic plumbing.
- Replace TV’s, VCR’s, DVD’s and program TV’s as required.
- Perform preventive maintenance in units and on equipment.
- Assist grounds personnel as directed. Use of lawn care equipment and snow removal equipment.
- Attend department and staff meetings as directed.
Skills Required:
- Knowledgeable use of hand & power tools, electrical test equipment, refrigeration equipment, plumbing tools & equipment, audio-visual equipment, telephone & telephone systems, office equipment, computer and computerized systems.
- Heavy work - exerting up to 100 lbs. of force occasionally.
- Must be able to convey information & ideas clearly.
- Must work well in stressful, high pressure situations.
- Ability to work in all weather conditions.
- Must have and maintain a valid driver’s license.
Education / Experience:
- Trade school or related training helpful
- High School diploma or equivalent required
Expected Conduct:
- Set the standard for professional behavior at all times
- Be knowledgeable of, practice and reinforce good business practices relating to harassment, discrimination and hostile environments in the workplace
- Remain aware and compliant with company policy and government regulations in regards to employment practices, as communicated by the Human Resources Department
- Remain calm during stressful and hectic periods
- Arrive at and depart from work according to schedule, or as needs dictate
- Make arrangements for job duties to be fulfilled during periods when you will not be present
- Always present a positive attitude about the Company and co-workers
- Abide by the words and intent of the Company Credos.
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Sales Representative - InnSeason Resorts The Falls at Ogunquit Sales Team - Ogunquit, ME
Job description
InnSeason Resorts The Falls at Ogunquit, in beautiful Ogunquit, Maine, seeks outgoing and upbeat individuals, with or without sales experience. We’re turning away business because we need more sales talent—could that be you? This is a great opportunity for someone who is looking for a more consistent and well-paying sales position or those who always thought they would be successful in the right sales environment. No sales experience required! We invest in you with top-notch training—just bring a can-do attitude!
This position includes:- Competitive Pay Plan - Salary plus Commission (Sales Representative earn $15.00/hr. + commission)
- **$2,000 Sign On Bonus (conditions apply)**
- Opportunity to Earn a $100K Annual Income
- Supportive Management Staff
- Ongoing Training
- Year-Round Position
- Weekends Mandatory
- Weekly Cash Bonuses & Monthly Bonuses
- Fun Working Atmosphere
- Free or Discounted Resort Vacations for Employees
- Hours of Operation are typically Friday-Sunday, 8:30am-4:00pm, but change based on tour volume.
If you have felt you have not yet reached your full potential and want the opportunity to grow, InnSeason Resorts could be what you have been looking for! We have more customers than we can handle—are you ready to join our team and grow with us?
New Hampshire Positions
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Housekeeper (Full & Part-time) - InnSeason Resorts Pollard Brook - Lincoln, NH
Job Description
Candidates should have cleaning experience in hospitality or retail setting, able to work in a fast paced environment and having great customer service skills is a must. Excellent opportunity to join a great team and with future opportunities for professional growth.
This is a year-round position.
Benefits Include:
- Health insurance
- Employee & family lodging discounts
- Restaurant, spa & winery discounts
- Flexible schedule
- Dental insurance
- Life insurance
- Vision insurance
- Paid time off incl. vacation, personal & holiday pay
- Referral program
- Bereavement and jury duty pay
Job Type: Full-time
Pay: $14.00 per hour Monday-Saturday and $17p/h on Sundays until Columbus Day.
COVID-19 considerations:
Employees are required to wear masks while on the property, maintain social distancing, and follow company Covid-19 protocols. Surfaces are sanitized on a regular basis, and as needed. PPE is provided if needed. -
Houseperson - InnSeason Resorts Pollard Brook - Lincoln, NH
Full time see schedule below and Part Time Thurs Fri Sun.
Replenishing supplies, making pickups in golf cart or van.
- Have previous stocking and delivery experience?* You help the resort team with delivery of linens and supplies to the housekeeping buildings.
If you have integrity and can jot down requests from our walkie talkies, this is the position that will help us both.
* Must have a valid driver license and obtain a copy of your driving record from the DMV (we will pay this fee).
- Uniform shirt, sweatshirt and jacket will be supplied for your resort uniform.
GENERAL RESPONSIBILITIES:
- Deliver items to guest units upon request from front desk. Sometimes a high chair, crock pot, or extra blanket
- Smile with your body language while helping a guest find their room or giving a restaurant recommendation
- Keep the Housekeeping Transit van organized, tidy and sanitized.
- Patrol hallways for pickups of bagged trash or linen in bins to transport to dumpster or laundry
- Stock closets for the next workday for the equally hard working housekeepers
- Can you work independently? If you've worked in a resort once you're familiar with the lay of the land and know where items are typically found you are relied upon to prep for the following day.
- Do you like to work efficiently? If you like to bounce around there will just be more to do in our 4 blocks of buildings.
- You will train with the Lead Houseman to understand, gain confidence and experience. Each day has its own rhythm. By listening to radio requests, writing down correctly and confirming delivery has been completed to a guest, helps everyone to happier and things moving along splendidly.
- If you have a strong core and can to lift up to 50 pounds max of our bagged fresh linens and to occasionally lift awkward items such as a cot, high chair, crib, then this will be a good fit!
- The Full Time Schedule:
- Tuesday 2pm-10:30pm
- Wednesday 2pm-10:30pm
- Thursday 2pm - 10:30pm
- Friday 9am - 5:30pm
- Sunday 10am - 6:30pm
Monday and Saturday off
Midshift Opportunities:
- 1:00pm-9:30pm Mon, Wed, Thur, Frid, Sat Tuesday and Sunday off
Job Type: Full-time
Pay: From $15.00 per hour
Benefits:
- 401(k)
- 401(k) matching
- Dental insurance
- Employee discount
- Health insurance
- Life insurance
- Paid time off
- Retirement plan
- Vision insurance
Schedule:
- 8 hour shift
- Holidays
- Night shift
- Weekends
Supplemental Pay:
- Tips
Shift Availability:
- Night Shift (Required)
Work Location:
- One location
This Job Is:
- Open to applicants who do not have a high school diploma/GED
- A good fit for applicants with gaps in their resume, or who have been out of the workforce for the past 6 months or more
- Open to applicants who do not have a college diploma
Benefit Conditions:
- Waiting period may apply
- Only full-time employees eligible
Work Remotely:
- No
COVID-19 Precaution(s):
- Personal protective equipment provided or required
- Plastic shield at work stations
- Social distancing guidelines in place
- Sanitizing, disinfecting, or cleaning procedures in place
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Publics - InnSeason Resorts Pollard Brook - Lincoln, NH
Job Description
Candidates should have cleaning experience in hospitality or retail setting. Candidates will be responsible for the cleaning and upkeep of common areas to ensure they are in presentable condition at all times. Excellent opportunity to join a great team with future opportunities for professional growth.
Benefits Include:
- Health insurance
- Employee & family lodging discounts
- Restaurant, spa & winery discounts
- Flexible schedule
- Dental insurance
- Life insurance
- Vision insurance
- Paid time off incl. vacation, personal & holiday pay
- Referral program
- Bereavement and jury duty pay
Job Type: Full-time
Pay: From $13.00 per hour
COVID-19 considerations:
Employees are required to wear masks while on the property, maintain social distancing, and follow company Covid-19 protocols. Surfaces are sanitized on a regular basis, and as needed. PPE is provided if needed. -
RiverWalk Resort at Loon Mountain - Lincoln, NH
Traveling (New England) Positions
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Sales Representative Contractor - InnSeason Resorts- Travel Throughout New England
Join the InnSeason Team!
Are you a dynamic and outgoing individual with a passion for travel and customer service? InnSeason Resorts, the Northeast's premier Vacation Ownership company, is seeking a dedicated Road/Inhouse Contract Sales Representative to join our team.
What You'll Do:
-Travel the Northeast: Explore beautiful New England destinations while providing exceptional customer service to our valued members.
-Build Relationships: Connect with existing members, understanding their needs and offering personalized solutions.
-Drive Sales: Identify opportunities to upgrade memberships and maximize customer satisfaction.
What We Offer:
-Guaranteed Income: Earn a guaranteed $250 per day for the first 4 weeks.
-Travel Perks: Enjoy complimentary accommodations for overnight trips.
-Professional Growth: Advance within a stable and successful company with a 15-year track record.
-Competitive Compensation: Earn a lucrative commission-based income.
To Qualify:
-Excellent communication and interpersonal skills
-A strong work ethic and self-motivation
-A passion for sales and customer service
-A valid driver's license and reliable transportationReady to embark on a rewarding career with InnSeason Resorts? Apply today!
Job Types: Part-time, Contract
Expected hours: No more than 20 per week
Schedule:-Weekends
-Holidays
License/Certification:
-Driver's License (Required)
Willingness to travel: 100%Work Location: On the road
3 Ways to Get Started
Apply now or contact us.
If you have a resume with work history and references. Complete this short form and attach your resume.
If you don't have a resume. Complete this online application with your work history and references.
If you have a question before you fill out an application, reach out to us, we would love to speak with you!
Our Values
As the Northeast’s premier resort developer, we understand that our success can only be attributed to our most valuable asset, our team members. As we continuously develop our culture and growth through innovation, we remain grounded in our values that continue to allow us to thrive as industry leaders.
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Integrity
First and foremost, we feel that this is the foundation of all that we do and encourage
this behavior through accountability and performance recognition in every role. -
Teamwork
Coming together as a team with a common goal or focus is the beginning of creating a lasting impact in the lives of everyone we touch.
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Excellence
We strive to embody this attitude in all that we do to be the best versions of ourselves for our family, our team and our customers.
Our signature resort properties
Our resorts are located in some of the most popular travel destinations in New England and our corporate office is located in the heart of Cape Cod. Whether you are a seasoned travel industry professional or have always dreamed of working in hospitality, we welcome you to learn more about what makes our destinations and company so special.

Pollard Brook
On a mountainside across from Loon Mountain is New Hampshire’s only Five-Star condominium resort, bordering the White Mountain National Forest.

Falls at Ogunquit
Ogunquit translates to “beautiful place by the sea.” The town holds true to that title today as home to one of the nation’s nicest beaches

Riverwalk resort
RiverWalk Resort at Loon Mountain, offers all the benefits of a second home including maintenance-free, resort style living through fractional and whole ownership.

Surfside
With the Atlantic Ocean at the front, Great Pond behind and Martha’s Vineyard on the horizon, this resort is surrounded by the spectacular natural beauty of Cape Cod.

Captain's Quarters
Located across the street from Falmouth Heights Beach overlooking Nantucket Sound, this is the perfect spot for your escape to Cape Cod.

HarborWalk
Overlooking Falmouth Harbor, this resort is minutes from the beach, downtown and the island ferries making it ideal for exploring the Cape.
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Equal Employment Employer
InnSeason Resorts is an equal opportunity employer that is committed to diversity and inclusion in the workplace. InnSeason Resorts prohibit discrimination and harassment of any kind based on race, color, sex, religion, sexual orientation, national origin, disability, genetic information, pregnancy, or any other protected characteristic as outlined by federal, state, or local laws.
This policy applies to all employment practices within our organization, including hiring, recruiting, promotion, termination, layoff, recall, leave of absence, compensation, benefits, training, and apprenticeship. InnSeason Resorts makes hiring decisions based solely on qualifications, merit, and business needs at the time. -
E-Verify
InnSeason Resorts participates in the Electronic Employment Eligibility Verification Program.
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Employment Disclaimer
InnSeason Management, Inc. manages resort properties on behalf of homeowners' associations and recruits on behalf of affiliate companies. At those properties the employer is the homeowners' association or the owners(s) of the affiliate business. InnSeason Management, Inc. assists the homeowners' associations and affiliate businesses with recruiting and hiring functions on behalf of the them. I understand and agree that, by applying through this site, I may be applying for a position with a company other than InnSeason Management, Inc.
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Accessibility Assistance
If you are an individual with a disability and need assistance completing the online application, please call 508-957-1880. Please leave a message and a member of our Human Resources team will return your call within three business days.
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Machine Readable Files
As part of the Transparency in Coverage Final Rule set forth by the U.S. Department of the Treasury, the U.S. Department of Labor, and the U.S. Department of Health and Human Services (referred to collectively as the “Tri-Agencies”), group health plans and health insurance issuers are required to make available to the public negotiated rates for all covered items with in-network providers, and historical payments to and billed charges from, out-of-network providers through machine-readable files (MRFs) posted on an internet website, updated monthly. These files will permit the public to have access to health plan payment information that can be used to understand health plan pricing and the cost for health care services.
InnSeason Management, Inc. https://www.harvardpilgrim.org/public/machine-readable-files
InnSeason Resort Pollard Brook https://www.harvardpilgrim.org/public/machine-readable-files
InnSeason Resort Surfside https://www.allwayshealthpartners.org/meet-us/transparency-regulations

