Seaside Vacations, an innovative Vacation Rental Company serving Chincoteague, Ocean City, and surrounding areas, is looking to grow our Team! Seeking reliable, self-motivated individuals with excellent communication skills, attention to detail, and a passion for the Eastern Shore. We provide our Guests with 5 Star Service & it takes 110% from all Team Members. We offer competitive pay (commensurate with skills & experience), a fun team environment, and opportunity for growth. Seaside Vacations/The Shore Group is an equal opportunity employer. Must be able to work weekends - some flexibility with hours. We value and appreciate our dedicated employees.

Guest Experience Specialist

Seaside Vacations is seeking a friendly, detail-oriented Guest Experience Specialist to serve as the first point of contact for our guests. This role is essential in delivering exceptional service throughout the booking and stay experience—handling reservations, responding to inquiries, and ensuring every guest interaction reflects our brand’s high standards.

Key Responsibilities

Reservations & Booking Management

• Handle incoming reservations via phone, email, website, and third-party channels (Airbnb, Vrbo, etc.)
• Accurately enter and manage bookings within the Property Management System (PMS)
• Assist guests in selecting properties that best fit their needs

Guest Communication

• Answer guest inquiries promptly via phone, PMS messaging, email, and OTA platforms
• Provide detailed information about properties, amenities, policies, and the Chincoteague area
• Maintain a warm, professional, and helpful tone in all interactions

Pre-Arrival & In-Stay Support

• Send confirmations, check-in instructions, and pre-arrival communications
• Assist guests with questions or issues before and during their stay
• Coordinate with internal teams (housekeeping, maintenance) as needed to resolve concerns

Channel & System Management

• Monitor and respond to messages across all booking channels in a timely manner
• Ensure accuracy and consistency of information across platforms
• Update guest profiles, notes, and reservation details in the PMS

Problem Solving & Service Recovery

• Address guest concerns quickly and professionally
• De-escalate issues and provide solutions that align with company policies
• Escalate complex issues when necessary

Qualifications

• Previous experience in hospitality, customer service, or reservations preferred
• Strong communication skills (phone, written, and digital messaging)
• Comfortable using technology, including PMS systems and online booking platforms
• Ability to multitask and stay organized in a fast-paced environment
• Positive attitude with a passion for delivering excellent guest experiences

Work Environment & Schedule

• Full-time
• Includes weekends and holidays
• What We Offer
• Opportunity to be part of a growing vacation rental company
• Supportive team environment
• Competitive pay
• Our Mission - At Seaside Vacations, we create memorable coastal experiences for our guests while maximizing value for our homeowners. Our Guest Experience Specialists play a key role in making every stay seamless and enjoyable

Property Stagers / Inspectors - Chincoteague

Seaside Vacations is hiring for our Seasonal Inspector Team! Our Property Inspectors are the reason we can maintain the excellent and consistent quality our Guests expect! Join us if you want to be a part of a fast-paced, fast-growing, fun-loving family company! We are looking for energetic, hard-working, team players!  Weekend work required.

Key Responsibilities: 

• Inspections for cleaning and maintenance issues
• Reporting and Scheduling Maintenance Issues
• Property Preparation
• Property Inventory and Staging
• This is a seasonal position with the possibility for staying year round. 

Housekeeping Positions - Chincoteague & Captain's Cove

Seaside Vacations is looking for hardworking housekeepers for the Summer Season & beyond! Great Pay and Bonuses! Join the fastest growing Team on the Island today! Setting up interviews ASAP, so don't wait! Must have own transportation & pass background check. Give us a call ~ we'll keep you busy, and help you achieve YOUR goals! 

Interested in applying for one of our open positions? Click the link below to download our application, then drop it off at our office at 4101 Main Street, Chincoteague or email it to our team! Housekeeping and Inspecting applications can be sent to [email protected]. All other applications can be sent to [email protected]!

Click HERE to download our application!