Wintergreen Short Term Rental Market Manager

Location: 
This position will require frequent, but not daily, visits to our properties in Wintergreen, and therefore would be ideal for candidates living within reasonable driving distance of Wintergreen. For candidates living further away from Wintergreen (ie Richmond, Northern VA), overnight lodging at our properties in Wintergreen can be provided if desired.

About New School Hosting:
New School Hosting is a rapidly growing boutique vacation property management company dedicated to unparalleled guest experiences while providing rental owners with worry-free property management. Our commitment to innovation and superior processes set us apart in the vacation rental industry. We manage some of the largest and best performing short term rental properties in Massanutten and Wintergreen.  The company formed in 2023 with just 3 properties, and now has 45 properties under management, with more being added every month.

Job Description:
We’re seeking a proactive and detail-oriented Market Manager to oversee our short-term rental properties in Wintergreen, VA. This person will serve as the point of contact for vendors, owners, and will also manage our on-site Wintergreen property manager. If you’re tech-savvy, organized, and thrive in an autonomous, dynamic environment—this is the role for you.

Responsibilities:

• Act as the primary contact for vendors and property owners in the Wintergreen market

   

• Build and maintain strong vendor relationships to ensure timely and quality service

   

• Know the ins and outs of each property under your care
  

   

• Identify and resolve property issues before guests or owners report them

   

• Oversee completion and quality of vendor work

   

• Maintain task tracking and property information via our Breezeway software

   

• Help onboard and become familiar with new properties

   

• Update digital guidebooks with local and property-specific information

   

• Monitor guest stays, respond to in-stay issues (with support from our virtual assistant team), and follow up on post-stay feedback or reviews

Requirements:

• Strong attention to detail and excellent organizational skills
  
  
• Self-starter with a high level of trustworthiness and follow-through
  
  
• Comfortable with technology and software tools
  
  
• Excellent communication and problem-solving skills
  
  
• Reliable transportation and valid driver’s license
  
  
• Must have access to computer, smartphone, and reliable internet

Pay:
This is a salaried position, with a starting salary range of $50,000-$70,000 per year, based on experience. Additionally, New School Hosting is offering a profit share program for 2026, and potentially beyond.

Hours:

40 hours per week. Generally we’re looking for M-F daytimes, but are flexible on the exact hours.  IMPORTANT NOTE: our guest communication team can handle the vast majority of guest questions, but we’ll want you to be available for the occasional night/weekend question that they need to escalate to you, as you will know more about the properties than they will. 

Benefits:

• Paid time off – Two weeks annually plus 9 paid holidays
  
  
• Opportunity for growth in a rapidly expanding company
  
  
• Hands-on training and support from a collaborative, tech-savvy team
  
  
• Health insurance benefits may be available on a case by case basis

How to Apply:

Interested candidates are invited to submit their resumes and why they are a great fit for New School Hosting. Please send to [email protected].

New School Hosting is an equal opportunity employer and encourages candidates of all backgrounds to apply. We thank all applicants for their interest; however, only those selected for an interview will be contacted.