Cape Cod Accounting Jobs in Massachusetts (NOW HIRING)

This is a part-time on-site role, primarily weekends (~20–25 hrs/week). You’ll be the point person for
guest communications and reservations through Hostfully, coordinate our housekeeping team
through Breezeway, and support our Controller with bookkeeping in QuickBooks Desktop. We’re a
small team in a busy seasonal market — the right person will find real ownership and variety in this
role, and for someone truly exceptional, there’s room for this to grow.

KEY RESPONSIBILITIES

Reservations & Guest Services

•       Manage all incoming bookings, inquiries, and guest communications through Hostfully property management software

•       Respond promptly and professionally to guest inquiries via phone, email, and online platforms

•       Process bookings, cancellations, and modifications accurately; send reservation confirmations

•       Coordinate check-in and check-out procedures, including door codes, digital guidebooks, and property orientations

•       Provide personalized local recommendations and attentive guest service throughout each stay

•       Track and manage orders for beach gear and baby gear rentals

•       Address guest concerns and escalate maintenance or property issues to the appropriate team member

Operations & Property Coordination

•       Coordinate with housekeeping staff on scheduling, property turnovers, and special requests using Breezeway

•       Communicate maintenance items and property issues to the operations team in a timely manner

•       Manage vendor calendars and reconcile service schedules with billing records

•       Assist with property quality checks to confirm properties are stocked and ready per reservation requirements

•       Track inventory across properties and initiate restocks for housekeeping and add-on products as needed

Accounting & Bookkeeping Support

Supports the full-time Controller with day-to-day bookkeeping tasks in QuickBooks Desktop:

•       Process accounts payable and accounts receivable entries in QuickBooks Desktop (Desktop version — not Online)

•       Review and process invoices; ensure all properties are billed accurately and on time

•       Generate client invoices and follow up on outstanding items professionally

•       Complete journal entries and general ledger posting as directed by Controller

•       Perform account reconciliations; assist with bank reconciliations

•       Organize and file accounting receipts and supporting documentation

•       Assist with ad-hoc Excel and QuickBooks tasks as directed by Controller

•       Flag discrepancies or outstanding items for Controller review

Office Administration

•       Keep the office organized and in good order throughout the weekend

•       Answer phones and respond to inquiries professionally

•       Process and organize incoming mail, receipts, and correspondence

•       Maintain tidy, accessible filing systems for documents and invoices

QUALIFICATIONS & REQUIREMENTS

Required

•       QuickBooks Desktop proficiency — Desktop version required (QuickBooks Online experience does not substitute)

•       Solid bookkeeping fundamentals: accounts payable, accounts receivable, invoicing, and basic reconciliation

•       Proficiency in Microsoft Excel for data entry, organization, and reporting

•       Exceptional attention to detail and commitment to accuracy

•       Strong organizational skills and ability to keep systems in order independently

•       Outstanding customer service skills with professional written and verbal communication

•       Proven ability to work independently and manage multiple tasks during a busy weekend environment

•       Fast learner with genuine willingness to learn new software — Hostfully and Breezeway training will be provided

•       High school diploma required; Associate’s or Bachelor’s degree in Accounting, Business, or related field preferred (or equivalent work experience)

Preferred

•       Prior experience with property management software (Hostfully, Guesty, or similar PMS platforms)

•       Background in vacation rental, hospitality, or property management operations

•       Bilingual in Spanish or Haitian Creole — helpful given our guest and staff mix, but not required

WORK ENVIRONMENT

This is a seasonal weekend position based in Eastham on Cape Cod. Peak season (Memorial Day through Labor Day) brings high booking volumes, elevated guest communication, and fast-paced coordination across properties. The right candidate is energized by a busy weekend environment, takes ownership of their responsibilities, and brings a positive, professional attitude to both guests and the team. We are a small, close-knit operation where every team member matters.

Seasonal Housing Available: For the right candidate, a seasonal housing option is available — a private camper at Maurice’s Campground. No pets permitted. Please inquire for details during the interview process.

InsideOut Properties of Cape Cod is a 100% woman-owned, award-winning vacation rental management company based on Cape Cod, MA, founded by Tara Goss. We offer full-service co-hosting on Airbnb and VRBO, guest readiness services, booking management, cleaning, linen services, and home watch — handling every detail from listing and promotion to turnovers and taxes so property owners can earn more with less stress. As an Airbnb SuperHost, VRBO Premier Partner, and VRMA Award of Excellence winner for Best Housekeeping, we are a close-knit team passionate about creating memorable guest experiences and treating every property like our own, inside and out.