Discover Your Perfect Chestnut Ridge Vacation Homes

Why Choose Rent By Owner for your Chestnut Ridge 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 Chestnut Ridge

When should you plan your Vacation Rentals stay?

Choosing the right time to vacation here can significantly enhance your experience, so consider seasonal patterns and local climate when planning your stay in this destination within the region.

Peak Season Highlights

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Summer (June to August)

During the summer months, you can enjoy warm weather and longer daylight hours, making it ideal for outdoor activities and exploring the natural beauty of the area.

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

This season offers stunning fall foliage, perfect for sightseeing and outdoor adventures. The pleasant temperatures make it a favorite time for visitors seeking scenic tranquility.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F

Off-Season Highlights

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Winter (December to February)

The winter months bring cooler temperatures, suitable for cozy stays and off-season exploration. You might find fewer crowds while enjoying a peaceful retreat here.

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

Early spring provides mild weather and blooming scenery, offering a quieter time for those who prefer fewer visitors and serene surroundings.

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

Weekly Weather Forecast for Chestnut Ridge

How to Book Your Chestnut Ridge 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 Chestnut Ridge

More Top-Rated Vacation Rentals in Chestnut Ridge 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 grilling with a fully equipped barbecue area, perfect for gatherings in the area’s scenic surroundings.
  • Relax on spacious patios or decks that offer stunning views of the natural landscape surrounding this destination.
  • Take advantage of private gardens or lawns, ideal for outdoor activities or simply unwinding in the fresh air.
  • Make use of outdoor fire pits to gather with loved ones and enjoy cozy evenings under the stars.
  • Benefit from access to well-maintained tennis courts or sports facilities available at select properties here.
  • Explore nearby hiking trails or nature walks directly from your rental, immersing yourself in the region’s lush environment.
  • Utilize outdoor swimming pools or hot tubs that are often included to enhance your relaxation experience here.

Top Attractions Around Chestnut Ridge

What attractions are nearby?

Within the area, you can enjoy outdoor activities like hiking and exploring scenic parks, providing a perfect way to experience the natural beauty of this destination.

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Family Activities

  • Chestnut Ridge Park: Spend quality time outdoors exploring the scenic trails, picnic areas, and playgrounds that make this local park a perfect family outing destination.
  • Miniature Golf in the Region: Enjoy a friendly game of miniature golf at one of the nearby courses, offering fun for all ages amidst the natural beauty of the area.
  • Local Nature Centers: Discover interactive exhibits and guided educational programs that introduce your family to the region’s diverse flora and fauna.
  • Family-Friendly Events: Check out seasonal festivals and community events held throughout here, providing memorable experiences for children and adults alike.
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Adult Activities

  • Hiking at Chestnut Ridge Park: Explore the scenic trails of the park to enjoy breathtaking views and outdoor adventure within reach of your rental here.
  • Visiting local wineries: Discover nearby wineries that offer wine tastings and tours, perfect for relaxing and savoring the region’s local flavors.
  • Playing golf at area courses: Tee off at nearby golf courses that provide a challenging yet enjoyable experience for golf enthusiasts staying in the surroundings.
  • Shopping at local boutiques: Browse charming shops and boutiques in the area for unique finds and souvenirs during your stay in this destination.

Other Places to Stay in Chestnut Ridge, NY

Sunbridge Institute
Sunbridge Institute Vacation Rentals
More Places to Stay Near Chestnut Ridge

Chestnut Ridge Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Nature Trails: Take advantage of the area's scenic trails to enjoy outdoor activities and experience the natural beauty that makes this destination special.
  • Plan Off-Peak Visits: Visiting during quieter times can help you fully appreciate the tranquility of your vacation rentals and avoid crowds in popular spots.
  • Discover Nearby Dining Options: Sample regional cuisine at local eateries to enhance your stay and gain authentic insights into the region's culinary scene.
  • Leverage Strategic Location: Choose a property that offers easy access to key attractions and amenities, maximizing convenience during your visit here.

Transportation Options

  • Local Bus Services: You can rely on local bus routes that connect this destination to nearby towns and transit hubs, making it convenient for exploring the region.
  • Taxi and Rideshare Services: Taxis and rideshare options like Uber and Lyft provide flexible transportation around the area, ideal for quick trips or when you prefer door-to-door service.
  • Car Rentals: Renting a car is a practical choice if you want the freedom to explore beyond here at your own pace, with several providers available nearby.
  • Airport Transfers: Shuttle services and private transfers operate between the closest airports and this destination, ensuring smooth arrivals and departures for your stay.

Local Customs Options

  • Local Farming Traditions: You’ll find that the area values its agricultural roots, with fresh produce and farmers' markets playing a central role in community life.
  • Seasonal Celebrations: Participating in seasonal festivals and parades is common here, offering authentic experiences rooted in local customs throughout the year.
  • Respect for Nature: The community embraces outdoor activities and conservation efforts, reflecting a deep appreciation for the natural beauty surrounding your stay.
  • Community Gatherings: Evening gatherings and local events are popular ways to connect with residents and immerse yourself in the region’s friendly atmosphere.

Chestnut Ridge Vacation Rental Frequently Asked Questions

1. What are the top vacation rentals in Chestnut Ridge?

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

2. Which vacation homes in Chestnut Ridge are best for families?

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

3. How many Rentbyowner vacation rentals are available in Chestnut Ridge?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 35 in the Chestnut Ridge 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 Chestnut Ridge. 

4. What is the cancellation policy for a vacation rental in this area?

The cancellation policy varies by property. Please review the specific listing details or contact the host directly for the most accurate information regarding cancellations and potential refunds.

5. How do I find out if my chosen property is available for my travel dates?

Availability is updated in real-time on the listing page. To confirm, you can check the booking calendar or reach out to the property owner for current availability during your preferred dates.

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

Additional fees such as cleaning, service charges, or security deposits are detailed within each listing. Always review these costs carefully before completing your reservation to ensure transparency.

7. What amenities are typically included in vacation rentals in this destination?

Amenities vary by property but often include essentials like Wi-Fi, parking, and kitchen facilities. For specific features, please consult the individual listing description or contact the host directly.

8. How can I communicate with the property owner if I have questions about my stay?

You can contact the owner directly through the messaging platform provided on the listing page. This ensures clear communication regarding your booking, special requests, or any concerns.