Elevate Your Property's Potential
Experience Unmatched Hospitality Management
Discover how Upward Hospitality transforms property management with personalized service and local expertise, ensuring both owners and guests enjoy exceptional experiences.
SEE OUR Services
With local expertise, hands-on service, and a commitment to excellence, we ensure that your condo operates smoothly year-round—so you can enjoy the benefits of ownership without the headaches. With our Sugarloaf Condo Management, let us take care of the details while you sit back, relax, and watch your investment thrive.
Worry-free ownership for property owners
Exceptional guest experiences that drive repeat bookings
Sustainable growth that increases long-term property value
Housekeeping & Cleaning
Baths, kitchens, bedrooms floors, and common areas
Basic Maintenance
Appliance check, repairs, plumbing, electrical
Snow & Lawn Care
Snow clearing, lawn care, seasonal exterior care
Grocery & Provisioning
Stocking essentials, décor, Seasonal readiness
Concierge Guest Check in
Meeting guests, delivering keys, brief orientation
Reservation Management
Streamlining guest experiences and bookings
Marketing Support
Listing updates, photography, optimization
Event & Retreat Planning
Professional Event Planner – Jillian Shaw
Housekeeping
Dusting, vacuuming, bathrooms, kitchen, common areas
Snow & Lawn Care
Snow clearing, lawn care, seasonal exterior care
Concierge Guest Check in
Meeting guests, delivering keys, brief orientation
Marketing Support
Listing updates, photography, optimization
Basic Maintenance
Appliance check, repairs, plumbing, electrical
Condo Provisioning
Seasonal readiness, décor, stocking essentials
Reservation Management
Streamlining guest experiences and bookings
Event & Retreat Planning
Professional Event Planner – Jillian Shaw
Get Your Free Quote Today
MINIMIZE YOUR STRESS
MAXIMIZE YOUR PROFITS
Ask about our Sugarloaf Condo Management and let our team take care of the marketing, sales, and maintenance of your property year-round while you enjoy the returns. With our proven systems and local expertise, your occupancy and revenue will climb to new heights—all the way to the summit.
An Experienced Team with Proven Results
30+ Years of experience
40+Local Properties
10,000+ Guests Served
MEET THE TEAM
Joe Christopher
Owner of Upward Hospitality & Sugarloaf Inn
Sugarloafer since: 1992
Favorite trail: Misery Whip
Background: Joe worked as a Ski Patroller at Sugarloaf in the 90s. He now runs businesses across Maine. He has owned and operated the Sugarloaf Inn & Shipyard Brew Haus since 2017.
Connor Cooper
Manager of Upward Hospitality & Sugarloaf Inn
Sugarloafer since: 2025
Favorite trail: Tote Road
Background: Connor grew up in the hospitality world and has turned that passion into a career of leadership and innovation. He became the Inn Keeper of Sugarloaf Inn in January 2025.
Frequently Asked Questions (FAQ)
We know that handing over the management of your property is a big decision. That’s why we’re here to provide clarity, transparency, and expert guidance every step of the way. Below, you’ll find answers to some of the most common questions about our services. If you don’t see what you’re looking for, feel free to reach out—we’re happy to help!
How does Condo Management service work?
We handle everything—from marketing and bookings to guest services, housekeeping, maintenance, and snow removal. Our team ensures your condo stays in top condition while maximizing rental income.
What makes Upward Hospitality’s management different from other services?
As a slopeside property with deep roots in the Sugarloaf community, we offer local expertise, hands-on service, and a team that understands what guests want. Our strategic marketing, concierge service, and snow removal set us apart.
How do you determine pricing for my condo?
We use a tiered pricing system that adjusts rates based on demand, seasonality, and competitor analysis to maximize your earnings while ensuring high occupancy.
Can I still use my condo when I want?
Absolutely! Owners can block out dates for personal use, and we’ll handle the rest to ensure seamless transitions between your stays and guest bookings.
How do I track my earnings and bookings?
You’ll receive regular financial reports and booking updates, ensuring full transparency on your condo’s performance.
How often is my condo cleaned?
Our team provides full-service housekeeping between guest stays, ensuring your property is always ready for the next arrival.
What happens if something in my condo needs repairs?
Our on-call maintenance team handles small repairs and upkeep, so you don’t have to worry about a thing.
What snow removal services are included?
We clear driveways, parking spots, walkways, and decks to ensure your guests have easy access no matter how much snow falls.
Do you prepare my condo for winter and summer seasons?
Yes! We handle seasonal opening and closing, ensuring your property is well-maintained year-round.
Our Legacy of Excellence
Upward Hospitality is a full‑service vacation rental management company based in Maine. Building on our success managing reservations and operations for rental units at the Sugarloaf Inn in Carrabassett Valley, we now offer a comprehensive suite of services—including housekeeping, property maintenance, grocery provisioning and snow removal—that let property owners enjoy truly hands‑off management. Our in‑house staffing model and commitment to personalized service ensure consistent quality and attention to detail. With a focus on the Carrabassett Valley region, our local knowledge and relationships help us support both owners and guests at the highest level.
Our mission is to provide personalized, full‑service vacation rental management that delivers worry‑free ownership, exceptional guest experiences and sustainable growth. We combine the resources of a professional management company with flexibility, care and local expertise. We help owners earn more, worry less and grow confidently.
Together, our team manages 40+ properties, has served 10,000+ customers, and brings over 30 years of hospitality and property management experience.