Eastern Shore Vacation Rentals is seeking an energetic, customer-focused professional to join our growing team as a Guest Experience & Reservations Specialist . This is a unique, cross-functional role that blends vacation rental sales, reservations, and guest services . You'll help prospective guests find the perfect vacation home, convert inquiries into bookings, ensure reservation accuracy, and provide exceptional service before, during, and after each stay. The ideal candidate enjoys building relationships, solving problems, and creating memorable guest experiences. Rather than simply processing reservations, you'll play an active role in maximizing occupancy, increasing repeat guests, protecting company revenue, and supporting our reputation for exceptional hospitality. Responsibilities naturally shift throughout the year, with greater emphasis on reservations and sales during booking season and guest services during peak travel months. Weekend availability is required as part of a shared team rotation to ensure guest and reservation coverage. This position also offers hybrid work flexibility , with a combination of in-office and remote work based on business needs, training, and demonstrated performance. Responsibilities Reservations & Sales Respond to reservation inquiries via phone, email, text, and online booking platforms. Convert guest inquiries into confirmed reservations through consultative sales and outstanding customer service. Assist guests in selecting the vacation home that best fits their needs. Process new reservations, reservation changes, cancellations, and extensions. Take ownership of the reservation payment process by ensuring reservation charges are accurate, guest payments are collected in full prior to check-in, and any discrepancies are resolved before arrival. Review reservation folios to verify charges, payments, fees, and reservation details for completeness and accuracy. Become knowledgeable about all company properties, amenities, and the Eastern Shore area to confidently assist prospective guests. Help identify opportunities to maximize occupancy, increase repeat bookings, and improve the guest experience. Guest Experience & Operations Coordinate guest communications before, during, and after each stay. Resolve guest concerns while coordinating with housekeeping, maintenance, vendors, and operations teams. Monitor and communicate the status of guest-related work orders. Maintain accurate reservation records, guest communications, and operational notes within company systems. Assist with onboarding new vacation rental properties and maintaining accurate property information. Partner with the management team in monthly reservation reconciliation by reviewing reservation records, payments, adjustments, and folios to help ensure accuracy and completeness. Help identify operational improvements that enhance guest satisfaction and efficiency. Qualifications Hospitality, vacation rental, customer service, sales, or related experience preferred. Excellent communication and relationship-building skills. Strong organizational skills with exceptional attention to detail. Ability to review reservation folios, understand charges and payments, identify discrepancies, and ensure reservations are complete and accurate. Comfortable learning reservation and property management software. Ability to multitask, prioritize, and work independently in a fast-paced environment. Strong problem-solving skills and sound judgment. Weekend availability as part of a shared team rotation. Ability to work both independently from home and collaboratively in the office. Compensation Competitive base pay based on experience, plus performance-based incentives tied to reservation sales, occupancy goals, and guest experience metrics.

Pay:

$45,000.00 - $60,000.00 per year

Benefits:

Health insurance Paid time off

Work Location:

Hybrid remote in Easton, MD 21601