Town of Highland Rentals by Owner

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Why Choose Rent By Owner for your Town of Highland vacation rental?

What makes our Rentals by Owner special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

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
Summer (June - August)

During the summer months, you'll experience warm weather perfect for outdoor activities and exploring the scenic surroundings of this destination.

Average Temperature Daytime: around 80°F (27°C) - Nighttime: about 60°F (16°C)
autumn
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.

Average Temperature Daytime: approximately 70°F (21°C) - Nighttime: roughly 45°F (7°C)

Off-Season Highlights

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Winter (December - February)

The winter season offers a quieter atmosphere for those seeking solitude and cozy accommodations in this region's rentals by owner.

Average Temperature Daytime: around 35°F (2°C) - Nighttime: near 20°F (-6°C)
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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.

Average Temperature Daytime: about 55°F (13°C) - Nighttime: close to 35°F (2°C)

Weekly Weather Forecast for Town of Highland

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

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.
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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.
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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

Minisink Battlefield County Park
Minisink Battleground Park
Eagle Institute
Brook House Gallery Incorporated
Highland Lake

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

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?

Cancellation policies vary by listing, so it's important to review the specific terms provided in the rental details or contact the owner directly before booking.

4. How do I communicate with the property owner during my stay?

You can typically reach out to the owner through the messaging system on the booking platform, allowing you to ask questions or address any concerns during your stay.

5. Are there any additional fees I should be aware of when booking a rental by owner here?

Additional fees such as cleaning, service charges, or security deposits may apply depending on the listing. Always review the full pricing breakdown before confirming your reservation.

6. What amenities are usually included in a rental by owner in this region?

Most rentals offer essential amenities like Wi-Fi, linens, and kitchen facilities. However, the specific amenities vary by property, so check the listing for detailed information.

7. Is there a minimum stay requirement for booking a rental by owner in this destination?

Minimum stay requirements depend on the property owner’s policies and may differ from one listing to another. Confirm the stay duration before completing your booking.

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