Discover Your Perfect Town of Highland Vacation Homes

Town of Highland Luxury Rentals

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Town of Highland Large Vacation Homes

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Why Choose Rent By Owner for your Town of Highland Vacation Rental Homes?

What makes our Vacation Rentals 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 Vacation Rentals stay?

Choosing the right time to visit here can enhance your experience, as the region offers distinct attractions and seasonal benefits that suit various interests throughout the year.

Peak Season Highlights

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Summer (June to August)

During the warm summer months, this destination experiences its peak season, attracting visitors seeking outdoor activities and scenic views. Booking your vacation rentals early ensures you secure the best options here in the area.

Average Temperature Daytime: around 80°F - Nighttime: about 60°F
autumn
Fall (September to November)

The vibrant colors of fall draw many travelers to the region during this time, making it another busy season for vacation rentals. Planning ahead guarantees access to desirable accommodations here in the destination.

Average Temperature Daytime: approximately 70°F - Nighttime: roughly 45°F

Off-Season Highlights

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Winter (December to February)

In the colder winter months, fewer visitors come, resulting in more availability and better rates for vacation rentals in this area. It’s an ideal time if you prefer a quieter escape here in the region.

Average Temperature Daytime: around 35°F - Nighttime: near 20°F
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Spring (March to May)

Early spring sees a slowdown in visitor numbers, offering a peaceful atmosphere and great rental deals. This is a perfect period to enjoy a relaxed stay in the destination without the crowds.

Average Temperature Daytime: about 55°F - Nighttime: approximately 35°F

Weekly Weather Forecast for Town of Highland

How to Book Your Town of Highland Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

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.

Explore and book the perfect rental in Town of Highland

More Top-Rated Vacation Rentals in Town of Highland Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

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 outdoor dining with a private patio or picnic area to make the most of the pleasant weather.
  • Relax on a spacious porch or deck, perfect for soaking up the scenic views of the surrounding region.
  • Take advantage of an outdoor swimming pool, ideal for cooling off during warmer months.
  • Explore nearby hiking or walking trails directly from your rental's doorstep for outdoor adventure enthusiasts.
  • Utilize a fire pit or outdoor fireplace for cozy evenings under the stars.
  • Benefit from well-maintained gardens or landscaped yards that enhance your outdoor experience.
  • Participate in outdoor recreational activities such as volleyball or badminton if available on the property.

Top Attractions Around Town of Highland

What attractions are nearby?

In this charming region, you can enjoy a variety of outdoor activities such as hiking, boating, and exploring scenic parks just moments from your vacation rental in the Town of Highland, New York.

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Family Activities

  • Hudson Highlands State Park: Explore scenic hiking trails and enjoy family picnics with stunning views of the Hudson River in this popular outdoor area nearby.
  • Dia:Beacon: Discover contemporary art exhibits at this renowned museum, offering engaging activities for children and adults alike within the region.
  • Walkway Over the Hudson State Historic Park: Take a leisurely stroll across one of the world's longest elevated pedestrian bridges, offering breathtaking river vistas perfect for family photos.
  • Local Farmers Markets: Experience the region's fresh produce and local crafts, providing a delightful outing for families seeking to immerse themselves in the area's local culture.
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Adult Activities

  • Wine Tasting Tours: Explore renowned local wineries in the area, offering tastings and vineyard tours that showcase the region’s celebrated viticulture.
  • Discover scenic trails along rivers and through lush landscapes, perfect for enjoying the natural beauty of this destination.
  • Historical Site Visits: Learn about the area's rich history by visiting notable landmarks and heritage sites that tell the story of this region's past.
  • Local Art Galleries: Immerse yourself in the vibrant arts scene by browsing through galleries featuring works from talented regional artists.

Other Places to Stay in Town of Highland, NY

Minisink Battlefield County Park
Minisink Battlefield County Park Vacation Rentals
Minisink Battleground Park
Minisink Battleground Park Vacation Rentals
Yulan
Yulan Vacation Rentals
Eagle Institute
Eagle Institute Vacation Rentals
Brook House Gallery Incorporated
Brook House Gallery Incorporated Vacation Rentals
Barryville
Barryville Vacation Rentals
Eldred
Eldred Vacation Rentals
Highland Lake
Highland Lake Vacation Rentals
More Places to Stay Near Town of Highland

Town of Highland Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Attractions: Take time to discover the area's unique outdoor activities and scenic spots that highlight the region's natural beauty.
  • Plan Ahead for Seasons: Consider the best times to visit, as seasonal changes in this destination can significantly enhance your experience.
  • Connect with Community Events: Participate in local festivals or markets to immerse yourself in the authentic culture of the region.
  • Optimize Your Stay: Choose a well-located vacation rental that offers easy access to top sites, ensuring a comfortable and convenient trip here.

Transportation Options

  • Car Rentals: Exploring the area is most convenient with local car rental services, giving you the flexibility to visit nearby attractions at your own pace.
  • Public Transit: Bus services connect this destination to surrounding towns and cities, providing an economical transportation option for travelers staying here.
  • Taxi and Rideshare Services: Taxis and ridesharing apps offer quick and reliable transportation, ideal for short trips within the region or reaching specific destinations.
  • Bike Rentals: The region’s scenic routes are best enjoyed on a bike, with rental shops available for exploring nature and local sights at your leisure.

Local Customs Options

  • Local Craftsmanship: You can observe the region’s tradition of handcrafted furniture and artisanal goods, reflecting the area's rich history of skilled craftsmanship.
  • Seasonal Festivals: Participating in seasonal festivals is a cherished custom here, offering you an authentic glimpse into the community’s cultural celebrations.
  • Farm-to-Table Dining: Embracing the local custom of farm-to-table cuisine allows you to enjoy fresh, locally sourced dishes during your stay.
  • Community Gatherings: Engaging in neighborhood events and gatherings helps you connect with locals and experience the welcoming spirit of this destination.

Frequently Asked Questions About Town of Highland?

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:

2. Which vacation homes in Town of Highland are best for families?

If you are looking for a family-friendly vacation home in Town of Highland, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Town of Highland:

3. 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 95 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. 

4. What is the cancellation policy for vacation rentals in the area?

Cancellation policies vary by listing. You should carefully review the specific terms on the property’s page or contact the owner directly to understand the refund and cancellation options available for your stay.

5. How do I know if my preferred dates are available?

Availability depends on the specific listing you’re interested in. Use the booking platform to check real-time availability or reach out to the property owner for confirmation of your desired dates.

6. Are there any additional fees I should be aware of when booking here?

Additional fees such as cleaning, service charges, or local taxes may apply. These details are typically outlined on the listing page or provided by the owner during the booking process.

7. What amenities can I expect in these vacation rentals?

Amenities vary by property but often include essentials like Wi-Fi, kitchens, parking, and heating. Review each listing’s description for the specific amenities offered in your chosen rental.

8. How do I contact the property owner if I have questions before booking?

You can communicate with the owner through the messaging system provided on the booking platform. This allows you to ask questions about the property, availability, or any special requests.