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.
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
Professional Marketing & Sales
Maximize visibility and bookings with strategic marketing
Dedicated sales and marketing teams focused on increasing occupancy and guest satisfaction
Guest Experience & Support
Providing guest assistance to ensure smooth check-ins, fast issue resolution, and great stays.
Proactive communication with guests before, during, and after visits
Condo Provisioning
Our easy and convenient Condo Provisioning is available 7 days a week to assist guests.
Our full condo provisioning utilizes a partnership with with Mainely Provisions for groceries & essentials
Snow Removal & Winter Prep
Driveways, walkways, decks & parking areas cleared after every snowfall for guest safety.
Comprehensive seasonal opening & closing for year round property care
Revenue Optimized Pricing Strategy
Dynamic pricing strategies to maximize rental revenue based on seasonality and demand
Housekeeping & Light Maintenance
Full-service cleaning between guest stays for a pristine space
On-call maintenance team for quick repairs, troubleshooting, and ongoing property care
GET IN TOUCH with us
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.
Explore Our Service Packages
Alpine Package
Owners who primarily self-manage but need reliable, on-the-ground support for winter & seasonal upkeep- Snow removal & winter prep
- 24/7 guest communication
Bluebird Package
Owners who want peace of mind knowing their property is cared for between guests or personal visits.- Snow removal & winter prep
- Light repairs
- General maintenance
Summit Package
Owners who want complete, hands-off management experience with thoughtful guest preparation included.- Bluebird Package plus
- Housekeeping
- Basic provisioning
First Tracks Package
Owners and guests who value convenience and luxury, with zero hassle. Custom plans available upon request- Summit Package plus customized solutions
- Full custom provisioning
- Dedicated account manager
Property Care & Maintenance Services
Trailside Package – Weekly Care & Peace of Mind
Weekly care subscription services, to keep your property functional, clean, and give you peace of mind.- $79/week | Includes:
- Weekly property check-in and inspection
- Light housekeeping, light cleaning, and dusting
- Appliance and system check including hot water, heating and cooling, and major appliances
- Supply and consumables check including toilet paper, soap, and other essentials
- Basic maintenance report for owners
- Perfect For:
- Owners who want consistent oversight and peace of mind between visits
Summit Trail Package – Premium Weekly Care & Guest-Ready Perks
Weekly premium care subscription service, for meticulous care and guest-ready perks.- $129/week | Includes:
- Weekly inspections of all rooms, appliances, and systems
- Enhanced housekeeping, dusting, vacuuming
- Linen refresh before your arrival with no full room turnovers
- Restock essential supplies and consumables
- Offer priority alert support for urgent matters
- Optional Add-On:
- Full housekeeping or post-guest cleaning at $50 per hour per staff member
- Optional full provisioning and welcome touches sourced by our team in partnership with Mainely Provisioning
- Perfect For:
- Owners who want full guest-ready preparation, enhanced care, and minimal effort
Premium Tier Addons
Premium Guest Experience & Sales Services
Don't trouble yourself with the details. Let our team optimize your stays- Includes:
- 24/7 guest communication & emergency support
- Concierge-style services (special requests, tailored recommendations, on-call assistance)
- Dynamic pricing tools, market analysis, and event-based surge optimization
- Perfect for: Owners who want to maximize bookings while providing a seamless, hotel-style guest experience.
Premium Marketing Services
Turn your property into a high-performing rental with targeted marketing and digital exposure- Includes:
- Professional multi-channel listings (Airbnb, VRBO, direct booking site, etc.)
- SEO and optimized listing content for visibility
- Paid digital advertising campaigns & promotions
- Perfect for: Owners who want their property to stand out in a crowded market and attract more guests.
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.
Brittany Gage
Manager of Sugarloaf Inn
Sugarloafer since: 2022
Favorite trail: Sluice
Background: Brittany joined the Sugarloaf Inn team in 2022 as a reservationist and quickly worked her way into a role in management. She is known for her exceptional guest service.
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.