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Hospitality and Business Expertise for an Exceptional Short Term Rental Experience

Gone are the days of expensive hotel stays and cookie cutter accommodations! Short term- rentals are an important and exciting component to a traveler’s weekend getaway or extended vacation.

At Upstate Outpost, we don’t believe that “clean and comfortable accommodations” or “great customer service” are standout qualities anymore – they should be the bare minimum expectations!

We strive to go above and beyond for both our property owners and their guests, focusing on the small, memorable details and one-on-one attention that can truly make a difference in your rental experience.

This comes through in our regular property walkthroughs, remembering our owners’ favorite coffee shop or wine variety, curating thoughtful welcome gifts for our travelers, and even staffing our own top tier cleaning team to make sure Upstate Outpost properties are luxuriously spotless
at all times.

We hold ourselves, our vendors, and our community partners to the highest standards so your stay in the Greenwood Lake area is nothing short of spectacular.

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We want to get to know every guest, and what will make their stay more enjoyable.


Travelers can request a list of their favorite staples, and we’ll stock the fridge and pantry for their stay.


If you’re a property owner coming back to town, we’ll make sure your grocery list is checked off and your local favorites are on hand so you can walk into “home sweet home.”


If entertaining the kids or impressing a partner on a special trip seems like a daunting task, we
can take all the guesswork out of our guests’ itinerary planning.


We have all the details of the very best seasonal activities happening year-round in the area, and can provide tailored recommendations and suggested event schedules to make planning a breeze.


One of the best parts of an Upstate stay is experiencing all the delectable food and unique local eats available in the upstate area!


We can give the inside scoop on our personal favorites, request reservations for special parties, and direct guests where to go to accommodate special eating habits or lifestyles.


We offer personalized communication efforts for each of our property owners they can effortlessly manage their personal stay dates, connect with our team, and stay updated on the status and upkeep of their home.

We proactively connect with our property guests through their preferred booking platform, social media channels, and local venues.


The [Upstate Outpost] hosts replied to any questions promptly and helpfully. The game room would entertain kids for hours. The house is surrounded in nature and is very quiet. The house looks just as advertised. Great for kids and adults. 100% recommend!

Evonne | Casual Modern
Lakefront/Gameroom/Greenwood Lake





A former resident of New Jersey, Mark Palmieri studied Hotel, Restaurant and Tourism Management at East Stroudsburg University of Pennsylvania. He brought his passion for fine food, drinks, and guest experiences to Greenwood Lake, New York as a co-owner of the area’s hottest restaurant, The Helm, in 2015.

The Helm has received numerous accolades throughout the years, including the titles of “Best in Hudson Valley” and “Best in Orange County.” Most recently, The Helm purchased a 55-ft. pirate ship that’s docked at the restaurant and is slated to become a unique offering to the tourism scene on the lake.

In addition to leading The Helm to success, Mark also manages multiple residential rental properties that are part of the restaurant’s building, as well as his personal residence with a rental cottage on the East Shore of Greenwood Lake.


From behind the bar, and out in the community, Mark has had the opportunity to build personal relationships with his customers and quickly recognized the need for a business that manages the day-to-day operations for successful property owners that are short on time.


Upstate Outpost was created to address this need, and Mark ensures that his network of strong local professionals give property owners peace of mind that they have the support and resources behind them to ensure the success and security of their rental property.


Lisa began her career as an editor in New York City for Facilities Design & Management, a trade publication dedicated to supporting C-level facilities managers in the commercial sector. She traveled the country to seek out the latest products and services, developed editorial content, and interviewed top experts in the industry to bring that knowledge back to the magazine’s readers who were in the trenches managing multi-million dollar properties.

Having built a base of editorial knowledge in the facilities management sector she then set her sights on the architecture and interior design side of the industry and joined the editorial staff at Contract Magazine, a sister publication of Facilities Design & Management.


After living and working in Manhattan, Lisa traded the concrete of the city for a home in the hills of Greenwood Lake where she has managed the Waterstone Inn, her family’s lakefront bed and breakfast, for the last 10 years.


With local insight into the wants and needs of visiting guests, second homeowners, and Airbnb operators, Lisa is now using her extensive guest services experience to help Upstate Outpost property owners maximize their properties’ reputation and revenue, while providing guests with a 5-star experience during every stay.



Family Run Makes All the Difference

While there are plenty of corporate property management firms that do the booking, cleaning, and guest transitions for a fee, Upstate Outpost bases our entire operation off serving the people and community we call home.

Both owners Mark and Lisa and their families live, work, and play here. They have built strong relationships throughout the area and know great people to connect with from professional services and local dining, to real estate deals and the best cup of coffee. They both run other successful businesses, and are deeply in-tune with the unforeseen challenges business owners may face.


They are respectful of the time and energy that property ownership takes to become a reliable passive income stream, and are happy to take the legwork on for their clients.

Mark and Lisa know better than to look at their owners’ properties from a micro-level of a single home. They have made it through global changes and economic ups and downs, and can guide property owners through unique market fluctuations with innovative solutions to minimizing risk and maximizing profit.

Mark and Lisa are homeowners themselves and understand all of the tasks needed to run and maintain a home. They act as a coach to others so that owners can understand the industry they are investing in.


Most importantly in this part of the country, they understand how different seasons can affect a home – from home fixtures and features to things like boats, patio
furniture, and more.

“Upstate Outpost is passionate about strengthening our community and other small businesses who support us and our property owners. We’d love the opportunity to show you what we’re all about and welcome you to the community we call home!”

Lisa + Mark

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