Hotel Resort Reservations Specialist

Company Description

Little Gem Resorts is a family-owned boutique hospitality company inspired by Mark and Gwenn Snider's passion for creating memorable island vacations for couples and families. The company owns and operates three highly regarded island properties:
The Winnetu Oceanside Resort on Martha’s Vineyard, The Nantucket Hotel + Resort on Nantucket, and The Lovango Resort + Beach Club on St. John, USVI. Each resort reflects a welcoming, personalized, and playful approach to high-end travel, offering curated yet accessible experiences. Loyal guests appreciate the warm atmosphere and thoughtful service, which Little Gem Resorts is extending as The Lovango Resort + Beach Club continues to open in phases.

Team members join a close-knit organization focused on guest satisfaction, authenticity, and meaningful connections.

The Hotel Resort Reservations Specialist is a full-time, hybrid role based in Wayland, MA, with some work-from-home flexibility (although 1 day in office, you must be driving distance to Wayland, MA). This role is responsible for handling reservation inquiries for all Little Gem Resorts properties, including responding to phone calls, emails, and online requests, and accurately entering reservations into the system.

Day-to-day tasks include providing detailed information about room types, packages, and amenities, confirming availability and pricing, and assisting guests with changes, cancellations, and special requests. The Specialist collaborates with resort teams to ensure smooth guest arrivals, supports receptionist and front office functions as needed, and helps coordinate food and beverage experiences or packages tied to reservations. This position emphasizes delivering friendly, professional customer service, resolving issues promptly, and representing the brand’s hospitality standards in every interaction.

• Strong Communication skills, including clear phone etiquette, professional email writing, and active listening.
• Experience with Reservations, booking systems, and accuracy in data entry and record keeping.
• Customer Service skills focused on empathy, problem-solving, and creating positive guest experiences.
• Familiarity with Receptionist Duties such as handling inquiries, managing schedules, and coordinating with front desk teams.
• Basic understanding of sales, upselling, and guest questions.
• Prior experience in hospitality, travel, or resort operations preferred.
• Comfort with computer systems, reservation software, and standard office applications.
• Ability to work in a hybrid setting from Wayland, MA, manage time effectively, and handle multiple tasks simultaneously.
• High school diploma required; additional education or certifications in hospitality or tourism are a plus.