Airbnb Management
Full-service Airbnb management for your short-term rental. Nationwide.
Highland, New York
In Highland, New York, guests can find a diverse range of Airbnb accommodations to suit various preferences and budgets. Options include charming bed-and-breakfasts nestled in the scenic Hudson Valley, offering a cozy and personalized experience. For those seeking more privacy, there are entire homes and cottages available, often featuring rustic decor and modern amenities, perfect for families or groups. Nature enthusiasts might enjoy staying in unique accommodations like cabins or yurts, providing a more immersive experience in the area's natural beauty. Additionally, there are stylish apartments and lofts in the town center, ideal for travelers who prefer a more urban setting with easy access to local shops and restaurants. Whether visitors are looking for a quaint retreat or a convenient base for exploring the region, Highland offers a variety of Airbnb options to meet their needs.
As of the latest information, Highland, New York, does not have specific local laws governing the operation of Airbnbs or short-term rentals. However, hosts must comply with Ulster County regulations and New York State laws, which may include safety, health, and zoning requirements. Hosts are generally required to collect and remit applicable taxes, such as the New York State sales tax and Ulster County's occupancy tax, on short-term rentals. It is advisable for hosts to stay informed about any changes in local regulations and ensure compliance with broader state and county requirements.
Managing an Airbnb in Highland, New York, involves several key tasks to ensure a smooth operation and positive guest experience. Hosts need to focus on maintaining the property by ensuring it is clean, well-stocked, and in good repair, which may involve coordinating with local cleaning and maintenance services. Effective communication with guests is crucial, from promptly responding to inquiries and booking requests to providing clear check-in instructions and addressing any issues during their stay. Additionally, hosts should optimize their listing by keeping the calendar updated, setting competitive pricing, and enhancing the property’s appeal through high-quality photos and detailed descriptions. Staying informed about local regulations and community guidelines is also essential to ensure compliance and foster good relations with neighbors. Finally, gathering and responding to guest reviews can help improve the service and attract more bookings.
Highland, New York, offers a charming and convenient location for Airbnb stays, particularly for those looking to explore the scenic Hudson Valley. One of the best areas to consider is near the Walkway Over the Hudson State Historic Park, which provides stunning views and easy access to hiking and biking trails. Staying close to the town center is also advantageous, as it offers a quaint, small-town atmosphere with local shops, cafes, and restaurants. Additionally, the proximity to the Hudson River and nearby attractions like the Franklin D. Roosevelt Presidential Library and Museum in Hyde Park make Highland a strategic base for exploring the region's rich history and natural beauty.
Highland, New York, presents a promising Airbnb investment opportunity due to its strategic location in the scenic Hudson Valley, which attracts tourists year-round. The area's proximity to popular attractions such as the Walkway Over the Hudson, numerous hiking trails, and wineries enhances its appeal to visitors seeking both outdoor adventures and cultural experiences. Additionally, Highland's close access to larger cities like Poughkeepsie and New York City makes it an attractive spot for weekend getaways. The local real estate market offers a range of property types, from charming historic homes to modern apartments, allowing investors to cater to diverse guest preferences. With a growing interest in rural and nature-focused travel, Highland stands out as a lucrative market for Airbnb investments.
As of the latest data, the average Airbnb revenue in Highland, New York, reflects a moderate yet promising market for short-term rental hosts. The area's proximity to popular attractions like the Hudson Valley and its scenic landscapes contribute to a steady demand for accommodations. Hosts in Highland typically see a range of earnings, influenced by factors such as property type, location, amenities, and seasonal variations. On average, hosts can expect to earn a few thousand dollars per month, with peak seasons, such as summer and fall, potentially boosting revenue due to increased tourist activity. The local market's performance is also shaped by competition and pricing strategies, making it essential for hosts to stay informed and adapt to trends to maximize their earnings.
Highland, New York, experiences a moderate occupancy rate for Airbnbs, with fluctuations largely influenced by its seasonal attractions and proximity to the Hudson Valley's natural beauty. The occupancy tends to peak during the fall months, as visitors flock to the area for its vibrant foliage and outdoor activities, such as hiking and apple picking. Summer also sees a higher occupancy rate, driven by tourists exploring the nearby Hudson River and enjoying local festivals. Conversely, the winter months typically witness a decline in bookings, as colder weather and fewer events lead to reduced tourist activity. Spring sees a gradual increase in occupancy as the weather warms and outdoor activities resume. Overall, Highland's Airbnb market is characterized by its seasonal appeal, with nature and regional events playing a significant role in attracting visitors.
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.