- USA
- New York
- Monticello
- Town of Highland
- Rentals by Owner
Discover Your Ideal Property Rental by Owner in the Scenic Town of Highland, New York
Discover Your Perfect Town of Highland Rentals by Owner
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Rentals by Owner
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Pet Friendly Vacation Rentals
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Town of Highland Rentals by Owner
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Pool
- Balcony/Terrace
- Sports/Activities
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Child Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Balcony/Terrace
- Air Conditioner
- Parking
- TV
- Parking
- Accessibility
- Security/Safety
- Air Conditioner
- Pet Friendly
- Security/Safety
Why Choose Rent By Owner for your Town of Highland vacation rental?
What makes our Rentals by Owner special?
Best Times to Visit Town of Highland
When should you plan your Rentals by Owner stay?
To make the most of your stay, consider planning your vacation during the region's optimal seasons when the weather and local events align to enhance your experience in this charming destination.
Peak Season Highlights
Summer (June - August)
During the summer months, you'll experience warm weather perfect for outdoor activities and exploring the scenic surroundings of this destination.
Fall (September - November)
Autumn brings a vibrant display of foliage, making it an ideal time to enjoy the area's natural beauty while booking a rental by owner here.
Off-Season Highlights
Winter (December - February)
The winter season offers a quieter atmosphere for those seeking solitude and cozy accommodations in this region's rentals by owner.
Spring (March - May)
Early spring is a quieter time to visit, with fewer visitors and the chance to enjoy the emerging blooms from your rental accommodation here.
Weekly Weather Forecast for Town of Highland
How to Book Your Town of Highland vacation rental
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Town of Highland
Common Rentals by Owner Amenities
What amenities can you expect?
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a spacious outdoor patio or deck for relaxing and dining amidst scenic views.
- Take advantage of private gardens or landscaped yards perfect for gatherings or unwinding.
- Make use of the outdoor grilling facilities to prepare meals while soaking in the natural surroundings.
- Benefit from access to nearby hiking trails, ideal for exploring the area's picturesque landscapes.
- Experience outdoor recreational areas such as fire pits or seating areas for evenings under the stars.
- Utilize the availability of bicycle racks or storage for exploring the region on two wheels.
- Access to outdoor swimming pools or lakeside spots for swimming and water activities if available locally.
Top Attractions Around Town of Highland
What attractions are nearby?
In this charming area, you can enjoy outdoor activities such as hiking and exploring local parks, along with nearby cultural experiences that make your stay both relaxing and engaging.
Family Activities
- Walkway Over the Hudson State Historic Park: You can enjoy a family-friendly stroll across this renowned pedestrian bridge, offering stunning river views and outdoor fun for all ages in this scenic region.
- Top of the Mountain Adventure: Here, your family can explore hiking trails and outdoor activities that showcase the natural beauty of the area’s hilly landscape and lush forests.
- Local Farmers Market & Craft Fair: Experience the regional charm by browsing local produce, handmade crafts, and family-oriented events in the heart of this destination’s community hub.
- Historical Riverfront Excursions: Discover the area's rich history with guided tours and boat outings along the river, perfect for engaging outdoor adventures with the family.
Adult Activities
- Wine Tasting Tours: Explore local vineyards nearby to enjoy private wine tastings and learn about the region’s renowned viticulture practices.
- Embark on scenic trails that wind through the area’s natural beauty, perfect for outdoor enthusiasts seeking a peaceful escape.
- Discover the region's rich history by exploring historic landmarks and museums that tell the story of this charming destination.
- Savor authentic regional cuisine at acclaimed restaurants, offering a delightful taste of the area's culinary heritage.
Other Places to Stay in Town of Highland, NY
Town of Highland Travel Tips
How Can You Make the Most of Your Stay?
- Research Local Regulations: Familiarize yourself with any town-specific rules or guidelines to ensure a smooth and hassle-free stay in this charming area.
- Choose a Well-Reviewed Rental: Select a rental with positive reviews on Rent By Owner to guarantee comfort and reliability during your visit.
- Plan Your Activities Accordingly: Explore nearby outdoor activities and cultural experiences to make the most of your time here, balancing relaxation with adventure.
- Communicate Clearly with Hosts: Maintain open communication with your rental owner to clarify check-in details and get local tips for an authentic experience.
Transportation Options
- Car Rentals: Renting a car offers you the flexibility to explore the scenic areas and attractions around this charming destination at your own pace.
- Public Transit: The regional bus services provide an affordable and convenient way to navigate through the town and nearby regions during your stay.
- Taxi Services: Taxis are readily available for quick, direct trips, ensuring comfortable transportation whenever needed in this welcoming area.
- Ride-Sharing Options: Ride-sharing platforms operate here, providing a reliable alternative for traveling comfortably within the region.
Local Customs Options
- Respect for Local Artisans and Crafts: You’ll find that supporting handcrafted goods and local artisans is an important custom here, reflecting appreciation for the area's creative community.
- Embracing Outdoor Lifestyle: Engaging in outdoor activities like hiking or kayaking is common, emphasizing a connection with the natural beauty of this region.
- Community Events and Festivals: Participating in seasonal festivals and community gatherings showcases the area’s friendly spirit and rich traditions.
- Environmental Conservation Awareness: Visitors are encouraged to practice eco-friendly habits, respecting the natural environment that defines this destination.
Frequently Asked Questions About Town of Highland Rentals by Owner
1. What are the top vacation rentals in Town of Highland?
There are a lot of options in Town of Highland. If you plan on staying in the Town of Highland area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Town of Highland:
- The Perfect Catskills Lake House
- Catskill Gem! Four bedroom on 20 quiet acres
- Indoor Pool, 11 yrs hosting, 7 bdrm, Hot Tub, Designer Home, Stunning Kitchen
- Lake Home on serene Highland Lake
- Cozy Catskills Farmhouse in Barryville near the Delaware River
- Catskills Woodland Escape: River, Festivals & More
- Secluded modern cabin with hot tub
- The Fern Hill Lodge: Cozy and Serene Getaway on 20 Private Acres
- Waterfront 1900s · Hot Tub · Eldred Homestead
- Escape to a Modern Waterfront Retreat in The Catskills.
2. How many Rentbyowner vacation rentals are available in Town of Highland?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 78 in the Town of Highland area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Town of Highland.
3. What is the cancellation policy for a rental by owner in this area?
4. How do I communicate with the property owner during my stay?
5. Are there any additional fees I should be aware of when booking a rental by owner here?
6. What amenities are usually included in a rental by owner in this region?
7. Is there a minimum stay requirement for booking a rental by owner in this destination?
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- Air Conditioner
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