Meet the Team

At Guesthouses we're passionate about sharing the unique and wonderful areas and events in our community here in Charlottesville, VA. Each member of our team, as well as each of our homeowners, have intimate knowledge of what makes a vacation rental stay special. Meet the team behind the scenes of your uniquely curated stays. 

Guesthouses Reservation Services in Charlottesville Virginia Vacation Rentals Now Hiring

Now Hiring - Guesthouses Reservations Manager

Why Guesthouses?

Guesthouses was acquired in 2016 by a Cassimir Club, a technology and marketing services organization focused on the vacation rental market. Since the acquisition, Guesthouses has undergone a transition from a 40-year old paper-based company with a dot-com era “website”, into a technology-forward, data-driven, marketing powerhouse. This transformation has built a foundation for Guesthouses to thrive, and is now ready to grow. While growth will be the focus of the next couple of years, we cannot lose sight of our commitment to excellent service for our guests and owners.  That is where you come in.


What we’re looking for:

An enthusiastic customer engagement and reservations manager that will ensure no day-to-day operations fall through the cracks.  The ideal candidate is self-motivated, personable, detail-oriented, communicates effectively, and is passionate about service excellence, making positive experiences in every interaction with team members, guests, and owners.


What you’ll do:

  • Respond to all reservation requests, as well as guest/owner comments, questions, and concerns in a prompt manner
  • Provide a welcoming atmosphere to potential guests when inquiring about a reservation
  • Screen guests to ensure properties will be treated with care and respect
  • Manage electronic calendars and bookings for all properties
  • Update and maintain current online property listings across multiple websites
  • Ensure timely collection of all payments
  • Review all guests following their stay and ensure those guests provide reviews
  • Revise pricing as needed to maximize revenue and occupancy rate
  • Work with our website vendor to update the Guesthouses website as necessary
  • Interface with accountants to record and remit transient & occupancy taxes and owner payments each week
  • Track revenue at the close of each month and build/update yearly forecast

Skills you’ll need:

  • Demonstrated experience within a customer service role, ideally within lodging/hospitality
  • Proficiency and demonstrated comfort with technology; specifically in using in Google Apps Suite (Calendar, Docs, Sheets) and Microsoft Office Suite (Word, Excel, Powerpoint)
  • Experience in learning new technology platforms, notably online listing sites (e.g., Airbnb, VRBO) and Escapia back-office software
Qualities for success
  • Effective communicator and relationship builder, with the ability to adapt your communication style to meet the needs of any audience
  • Extremely organized and detail oriented
  • High energy and enthusiasm
  • Effective time manager, with the ability to effortlessly juggle different tasks and prioritize (e.g., booking a reservation, responding to a critical review, updating an existing listing)
  • Self-motivated worker, as you may be working by yourself on most days
  • Problem Solver: so that when something doesn't go according to plan, you can quickly adapt and respond with a creative solution
  • Ability to analyze and interpret data, and recommend solutions for operational improvements
  • Strong sense of ownership, in that you will help identify areas for improvement and help drive those improvements forward 

The details and of course, the perks!

Expectation: Full-time office hours (9am-5pm), on-call with regularly checking and responding to reservation requests/urgent matters nights and weekends

Location: Remote (in Charlottesville) as desired, at office for transition/training period mandatory, and as needed for ad hoc projects


  • Salaried role, with bonus structure based on revenue goals
  • Remote work possible
  • Develop close relationships with influential Charlottesville residents
Contact to apply and for more information.
Rachel Breuhaus

After arriving in Charlottesville in 2013, it was immediately clear to Rachel that this was a special place.  The kind of home-town community with a thriving University atmosphere that reminded her of her many years in Chapel Hill, NC.


Rachel started her career in vacation rentals by managing and marketing her family and friends’ vacation rental properties. Through using modern marketing tactics in a tradition rich industry, Rachel was able to see first-hand the financial impact of fresh thinking. Leveraging this idea, Rachel pursued her MBA at the University of Virginia’s Darden School of Business, where she received the full merit-based Batten Scholarship for Entrepreneurship. At commencement, she was also honored with the C Stewart Sheppard Distinguished Service Award.


While at Darden, she started her own company, Cassimir Club, LLC to aid vacation rental homeowners in marketing and guest correspondence. Shortly after graduation, Cassimir Club acquired Guesthouses, the Charlottesville-based reservation service, making Rachel the fourth woman to own the company in its 40+ year history.

Molly McFarland
Director of Special Projects

Molly McFarland was born and raised in Williamsburg, Virginia and graduated from the University of Virginia in 2007 with a Bachelor of Arts. Molly worked in D.C. at International Justice Mission and at The National Gallery of Art for four years. While her husband was at Darden from 2011-2013, Molly worked for the Center for Entrepreneurial Leadership that worked with Darden and community members on starting businesses. She ran the summer incubator program. Molly and her family moved to Dallas, Texas for four years and had two children. They just returned to Charlottesville and are raising their family and enjoying being back in their happy place!