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Discover Your Perfect Orange County Rentals by Owner

Orange County Rentals by Owner

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10.0 (5 Reviews)
Apartment
Montgomery Modern Luxury Stays
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
More Top-Rated Rentals by Owner in Orange County Area

Why Choose Rent By Owner for your Orange County 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 Orange County

When should you plan your Rentals by Owner stay?

Choosing the ideal time to vacation here can enhance your experience, allowing you to enjoy the region's natural beauty and local events while making the most of your rental by owner in Orange County, New York.

Peak Season Highlights

summer
Summer (June to August)

During the summer months, this area experiences warm weather and longer daylight hours, making it ideal for outdoor activities and enjoying the natural beauty of the region.

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

Autumn is a popular season here, with vibrant foliage attracting visitors looking to experience the scenic landscapes and pleasant weather before winter sets in.

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 see cooler temperatures and quieter surroundings, providing a peaceful retreat away from peak crowds for those seeking a cozy getaway.

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

Early spring offers milder weather and blooming landscapes, although it is considered off-peak compared to summer and fall, making it perfect for quiet exploration and relaxation.

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

Weekly Weather Forecast for Orange County

How to Book Your Orange County vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. 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 Orange County

More Top-Rated Rentals by Owner in Orange County Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner 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 a private outdoor space with a patio or deck ideal for relaxing or entertaining during your stay.
  • Make the most of your visit with a spacious backyard perfect for outdoor activities and gatherings.
  • Take advantage of outdoor dining areas to savor meals while soaking in the natural surroundings.
  • Unwind in a hot tub or Jacuzzi available at many rentals, offering a luxurious way to relax after exploring the area.
  • Benefit from access to a fire pit, ideal for cozy evenings and making memories under the stars.
  • Appreciate landscaped gardens or greenery that enhance the charm and tranquility of your vacation experience.
  • Utilize outdoor recreational equipment such as grills, play areas, or sports courts often included in this destination’s rentals.

Top Attractions Around Orange County

What attractions are nearby?

While exploring here, you'll find a variety of outdoor activities and local attractions nearby to enjoy during your stay in Orange County, offering a perfect blend of relaxation and adventure in the region.

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Family Activities

  • The Hudson Highlands Nature Museum: Engage your family with interactive exhibits and outdoor adventures that showcase the natural beauty of the region.
  • : Step back in time at this western-themed park, perfect for fun-filled family days exploring cowboy culture and live entertainment.
  • The Orange County Arboretum: Discover a peaceful setting where you can stroll through beautifully landscaped gardens and enjoy educational programs for all ages.
  • The Castle Fun Center: Experience endless indoor and outdoor activities, including arcade games, mini-golf, and laser tag designed to entertain every family member.
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Adult Activities

  • Exploring the Hudson Highlands State Park Preserve: Immerse yourself in scenic hiking trails and breathtaking views within this natural gem, perfect for outdoor enthusiasts visiting nearby rentals.
  • Enjoying the Local Wineries and Craft Breweries: Discover the region’s vibrant wine and craft beer scene with tours and tastings that highlight the area's unique flavors, conveniently accessible from your rental accommodation.
  • Discovering Historic Sites and Museums: Dive into the area's rich history by visiting museums and historic landmarks that offer insightful experiences just a short drive from your vacation rental.
  • Participating in Water Activities on the Hudson River: Take advantage of boating, fishing, or simply relaxing by the river to unwind and enjoy the tranquil waters in the vicinity of your stay.

Other Places to Stay in Orange County, NY

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Wallkill
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Monroe
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Town of Highlands
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Middletown
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Warwick
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Highland Falls
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Town of Deerpark
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Greenwood Lake
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Goshen
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Chester
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Montgomery
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Orange County Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for Local Events: Check the regional event calendar to align your stay with festivals or cultural activities, enhancing your experience in this welcoming area.
  • Explore Unique Rentals by Owner: Search for vacation homes that offer personalized touches and local insights, ensuring a memorable visit in this destination.
  • Utilize Seasonal Recommendations: Take advantage of seasonal activities and outdoor adventures available here to make the most of your time in the region.
  • Respect the Neighborhoods: Be mindful of local customs and community guidelines to enjoy a pleasant and authentic experience during your stay in the area.

Transportation Options

  • Orange County Transit Authority: Provides reliable bus services that connect various towns and attractions within the area, making local travel convenient.
  • New York State Thruway (Interstate 87): Offers easy access for driving in and out of the region, ideal for exploring nearby destinations with your rental vehicle.
  • Stewart International Airport: Serves as the primary airport nearby, offering domestic flights and rental car services for seamless arrivals and departures.
  • Taxi and Rideshare Services: Available throughout the area, these options provide flexible transportation to and from your rental property with ease.

Local Customs Options

  • Welcome Traditions: You will find that greeting visitors with warmth and friendliness is a cherished custom here, reflecting the region's welcoming spirit.
  • Local Festivals: Participating in seasonal festivals is common, providing an authentic way to experience the area's community-oriented culture.
  • Food Customs: Enjoying locally sourced and traditional dishes is a key part of the region's culinary customs, offering a taste of local heritage in every meal.
  • Respect for Nature: There's a strong emphasis on preserving the natural beauty of the area, encouraging eco-friendly practices during your stay.

Frequently Asked Questions About Orange County Rentals by Owner

1. What are the top vacation rentals in Orange County?

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

2. How many Rentbyowner vacation rentals are available in Orange County?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 625 in the Orange County 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 Orange County. 

3. What is the cancellation policy for rental properties in Orange County, New York?

The cancellation policy varies for each property listed by owners. You should review the specific listing details or contact the owner directly to understand the terms and any potential fees associated with cancellations.

4. How do I communicate with the property owner before booking my stay in this region?

You can use the messaging feature on the rental platform to reach out to the property owner. This allows you to ask questions about the rental, clarify details, and ensure the property meets your needs before confirming your reservation.

5. Are there any house rules or amenities I should be aware of when booking a rental here?

Details about house rules and amenities are typically provided in the property listing. It’s important to read these carefully and contact the owner if you have specific questions or special requests to ensure a smooth stay.

6. What is the process for checking into and out of a rental in the area?

Check-in and check-out procedures are outlined by the property owner in the listing. Most rentals offer flexible options, but it’s best to confirm the exact times and any requirements directly with the owner prior to your arrival.

7. Is there a minimum stay requirement for vacation rentals in this destination?

Minimum stay policies vary among listings. Be sure to verify the duration required for your selected rental by reviewing the property details or contacting the owner directly to avoid any issues with your booking.

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More Top-Rated Rentals by Owner in Orange County Area