Discover Your Perfect Highlands Vacation Homes

Highlands Luxury Rentals

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Why Choose Rent By Owner for your Highlands 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 Highlands

When should you plan your Vacation Rentals stay?

To make the most of your stay, consider visiting during the optimal seasons when the weather enhances your experience in this destination, allowing you to enjoy all that the area has to offer at the right time for your vacation.

Peak Season Highlights

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Summer (June to August)

During the warm summer months, the area experiences higher demand as visitors flock to enjoy outdoor activities and scenic drives, making it an ideal time to book vacation rentals for a vibrant getaway.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
autumn
Fall (September to November)

The region's stunning fall foliage attracts travelers seeking picturesque landscapes and outdoor adventures, creating peak demand for vacation rentals in this colorful season.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 45°F to 55°F

Off-Season Highlights

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Winter (December to February)

Colder weather and fewer visitors characterize the winter months here, offering a peaceful retreat with cozy vacation rentals perfect for enjoying serene surroundings.

Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 30°F
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Early Spring (March to May)

Before the peak spring travel rush, this period offers a quieter experience with mild temperatures, making it a great time to find affordable vacation rentals and explore at your own pace.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 35°F to 45°F

Weekly Weather Forecast for Highlands

How to Book Your Highlands 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 Highlands

More Top-Rated Vacation Rentals in Highlands 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 spacious outdoor patios or decks perfect for relaxing and entertaining.
  • Take advantage of private gardens or landscaped yards to immerse yourself in nature.
  • Make the most of outdoor dining areas, ideal for savoring local cuisine amidst scenic views.
  • Utilize well-maintained grilling stations or outdoor kitchens for cookouts with family and friends.
  • Explore nearby walking trails or access to nature paths directly from your rental.
  • Relax by outdoor fireplaces or fire pits during cool evenings under the stars.
  • Benefit from outdoor swimming pools or hot tubs to unwind after exploring the area.

Top Attractions Around Highlands

What attractions are nearby?

Within this scenic region, you can enjoy a variety of outdoor activities and cultural experiences that highlight the best of Highlands in White Plains, New York, ensuring your stay is both relaxing and engaging.

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Family Activities

  • White Plains Children's Museum: Engage your family with interactive exhibits and hands-on activities that inspire learning and fun for children of all ages.
  • : Explore scenic hiking trails, scenic picnic spots, and outdoor adventures amidst stunning natural beauty just a short drive from here.
  • Playland Park: Enjoy classic amusement rides and seasonal events perfect for a day of family entertainment in the area.
  • The Westchester County Center: Attend family-friendly events, shows, and exhibitions that provide enjoyable experiences for everyone in your group.
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Adult Activities

  • Hiking and Nature Walks: You can explore scenic trails that showcase the area's natural beauty, perfect for outdoor enthusiasts seeking fresh air and stunning views.
  • Golfing Experiences: Enjoy a day on well-maintained golf courses tailored for all skill levels, offering both relaxation and a challenge amidst the region’s lush landscapes.
  • Local Art Galleries and Exhibits: Discover the vibrant arts scene with visits to local galleries that feature regional artists and unique exhibitions in this cultural hub.
  • Wine Tasting Tours: Indulge in wine tasting experiences at nearby vineyards, where you can sample regional wines while learning about the area's viticulture history.

Highlands Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Activities Ahead: Research local events and outdoor activities to maximize your experience in this scenic area, ensuring you make the most of your stay in Highlands.
  • Choose the Right Vacation Rental: Select a property that offers convenient access to popular destinations here, adding comfort and ease to your visit.
  • Explore Local Dining Options: Take the opportunity to enjoy regional cuisine at nearby restaurants to immerse yourself in the area's culinary culture.
  • Pack Accordingly for the Climate: Be prepared for the weather variations common to this region by packing versatile clothing, allowing you to comfortably enjoy your holiday.

Transportation Options

  • White Plains Transit Authority: This regional transit service offers convenient bus routes that connect you to key areas within the region and beyond.
  • Metro-North Railroad: A reliable commuter train system providing quick access to New York City and other parts of the region, ideal for day trips or commuting.
  • Rental Car Services: Several rental agencies operate in the area, giving you flexibility to explore this destination and surroundings at your own pace.
  • Private Transportation Options: Taxis and ride-sharing services are readily available, offering comfortable and direct travel within and around the area.

Local Customs Options

  • Welcoming Community Events: Embrace the region's tradition of community gatherings that celebrate local culture and foster a strong sense of belonging.
  • Respect for Nature: Visitors often observe a deep appreciation for the natural surroundings, reflected in outdoor customs and conservation efforts here.
  • Local Dining Etiquette: When enjoying regional cuisine, you'll find that sharing meals and engaging in friendly conversation are key aspects of social interaction.
  • Seasonal Festivals: Participating in the area's seasonal celebrations allows you to experience authentic local customs and traditions firsthand.

Frequently Asked Questions About Highlands?

1. What are the top vacation rentals in Highlands?

There are a lot of options in Highlands. If you plan on staying in the Highlands area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Highlands:

2. How many vacation rentals have private pools in Highlands?

There are 8 vacation rentals with private pools near Highlands. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Highlands are best for families?

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

4. How many Rentbyowner vacation rentals are available in Highlands?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 148 in the Highlands 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 Highlands. 

5. What is the cancellation policy for vacation rentals in Highlands near White Plains?

Cancellation policies vary depending on the property listing. You should review the specific cancellation terms outlined in the listing details or contact the property owner directly to understand your options and any applicable fees.

6. How do I confirm the availability of a vacation rental in this area?

Availability can be checked by viewing the calendar on the listing page. If you have questions about booking dates or need further assistance, reaching out to the property owner is recommended for real-time confirmation.

7. Are there specific check-in and check-out times for vacation rentals here?

Check-in and check-out times are typically specified in each listing. To ensure a smooth arrival and departure, consult the details or communicate with the property owner before your stay.

8. What amenities are usually included in Highlands vacation rentals near White Plains?

Amenities vary by property, but common features include Wi-Fi, parking, and full kitchens. For a complete list of what’s included, review the listing description or contact the host directly.

9. What steps should I take if I need to modify my reservation for a Highlands vacation rental?

Reservation modification policies differ by host. It's best to review the cancellation and modification terms listed on the property page or contact the property owner to discuss your needs.