Airbnb Management
Full-service Airbnb management for your short-term rental. Nationwide.
Highland Falls, New York
In Highland Falls, New York, guests can find a variety of Airbnb accommodations that cater to different preferences and needs. The area offers charming cottages and cozy cabins that provide a rustic and intimate experience, often nestled in the scenic surroundings of the Hudson Valley. For those seeking a more modern stay, there are contemporary apartments and homes equipped with all the necessary amenities for a comfortable visit. Additionally, some properties offer unique experiences, such as historic homes that reflect the rich history of the region or properties with stunning views of the nearby mountains and the Hudson River. Whether visitors are looking for a peaceful retreat or a convenient base to explore the nearby attractions, such as West Point Military Academy and Bear Mountain State Park, Highland Falls offers a diverse range of Airbnb options to suit various tastes and budgets.
As of the latest information, Highland Falls, New York, does not have specific local laws governing the operation of Airbnbs or short-term rentals. However, hosts must comply with New York State regulations, which may include safety and health standards applicable to all rental properties. While there are no unique local ordinances, hosts should be aware of state-level tax obligations, such as collecting and remitting sales tax and possibly occupancy taxes, depending on the nature of the rental. It is advisable for hosts to consult with local authorities or a legal expert to ensure compliance with any applicable state or county regulations and tax requirements.
Managing an Airbnb in Highland Falls, New York, involves several key tasks to ensure a smooth operation and positive guest experience. Hosts need to focus on maintaining the property, which includes regular cleaning, restocking essentials, and ensuring all amenities are in working order. Effective communication with guests is crucial, from promptly responding to inquiries and booking requests to providing detailed check-in instructions and local recommendations. Pricing strategies should be regularly reviewed to remain competitive, taking into account seasonal demand and local events, such as those related to the nearby United States Military Academy at West Point. Additionally, compliance with local regulations and tax requirements is essential to avoid any legal issues. Overall, successful Airbnb management in Highland Falls requires attention to detail, excellent customer service, and strategic planning.
Highland Falls, New York, is a charming village located near the United States Military Academy at West Point, offering a blend of historical significance and natural beauty. When considering an Airbnb stay, the best areas are those that provide easy access to both the academy and the scenic Hudson River. Staying near Main Street is ideal for visitors who want to enjoy local dining and shopping, as well as the convenience of being close to the West Point Museum and Visitor Center. For those seeking a more tranquil experience, accommodations near Bear Mountain State Park offer stunning views and outdoor activities like hiking and picnicking. Both areas provide a cozy, small-town atmosphere with the added benefit of being a short drive from the cultural and recreational opportunities of the Hudson Valley.
Highland Falls, New York, presents a promising market for Airbnb investment due to its proximity to the United States Military Academy at West Point, which attracts a steady stream of visitors, including families of cadets, alumni, and tourists interested in the academy's history and events. The village's charming small-town atmosphere, combined with its location near the scenic Hudson River and the Hudson Highlands State Park, offers a desirable retreat for nature enthusiasts and those seeking a peaceful getaway from the hustle and bustle of New York City, which is just an hour's drive away. Additionally, the area's rich history and cultural attractions, such as the West Point Museum and nearby historic sites, enhance its appeal as a year-round destination, potentially leading to high occupancy rates and a good return on investment for Airbnb hosts.
As of the latest data, Highland Falls, New York, presents a modest yet promising market for Airbnb hosts. The average revenue for Airbnb properties in this area is influenced by its proximity to popular attractions such as the United States Military Academy at West Point and the scenic Hudson River Valley. Hosts in Highland Falls typically see a steady stream of guests, particularly during peak tourist seasons and events at West Point. While the average revenue may not reach the heights of larger urban centers, the combination of a charming small-town atmosphere and strategic location contributes to a stable income for local Airbnb operators.
Highland Falls, New York, experiences a fluctuating Airbnb occupancy rate influenced by its proximity to the United States Military Academy at West Point and the seasonal appeal of the Hudson Valley. The occupancy rate tends to peak during the summer months, from June to August, when tourists flock to the area for outdoor activities, scenic views, and local events. Additionally, the fall season, particularly September and October, sees a surge in visitors drawn by the vibrant autumn foliage. Conversely, the winter months typically witness a decline in occupancy, as colder weather and fewer events lead to reduced demand. However, special occasions such as West Point graduation and homecoming events can temporarily boost occupancy rates during off-peak times.
Why Choose Checkmate Rentals?
![]() | Other Property Managers | |
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Cost | Starting at 15% fee | 25-40% fee |
Guest Communications | Guest response within 10 minutes, 24 hours a day | Sporadic guest communications |
Host Communications | Designated host call in phone line | Bot response assistants |
Insurance | Full damage protection for every reservation | Unreliable insurance coverage |
Contract | No annual agreements | Contract lock-ins |
Checkmate Rentals

Attract Guests
List on top booking sites
Optimize listings for SEO
Feature show-stopping photos
Competitive, dynamic pricing
Mangage Operations
Tailored pricing algorithms
24/7 guest service
Reliable, professional cleaning
Restocking & inventory management
Maintenance coordination


Host Care
Unlimited owner stays
Flexible contract options
East to use host portal
Set it and forget it billing
Exclusive insurance discounts via our partner network
Get in touch with us.

Checkmate Rentals is a full-service property manager. That means the Airbnb listing, the home, the guest and the work is our responsibility.
Local Team Support
Know that you have a friendly, accessible team right up the road to handle any property needs.
Guest Screenings
Book only the most qualified guests 25 and over who’ll enjoy your home the right way.
Unlimited Owner Use
Block off your vacation days with ease, and enjoy your home as often as you want.
Reliable Property Maintenance
Keep your home running smoothly around the clock with a fast, reliable maintenance team.
Transparent Finances
Transparent Finances Booking payouts get paid directly to you for full financial transparency. We never handle your money.
Fast 24/7 Guest Communication
Make every guest feel cared for with industry best response times of 1-15 minutes day and night.
Marketing
Target, attract & book qualified guests with photography, email marketing, and optimized listings.
Revenue Management
Get the competitive edge with dynamic pricing and rates optimized daily by your pricing manager.

Ready to make the jump?
Let's get started! Schedule a call today to learn more about Checkmate Rentals.