Discover Your Perfect Woodbury Vacation Homes

Why Choose Rent By Owner for your Woodbury 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 Woodbury

When should you plan your Vacation Rentals stay?

Choosing the right time to visit ensures you make the most of your stay in this destination, allowing you to enjoy its unique seasonal appeal and local events at their best.

Peak Season Highlights

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Spring (March to May)

During spring, the area comes alive with vibrant scenery, making it an ideal time to explore comfortably. The weather is mild, providing perfect conditions for outdoor activities and sightseeing.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F
autumn
Fall (September to November)

Autumn offers stunning foliage and pleasant temperatures that enhance your visit here. It's a popular season for travelers seeking picturesque landscapes and comfortable weather.

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

Off-Season Highlights

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Summer (June to August)

While summer is lively, it also marks a quieter period for those seeking fewer crowds and more relaxed surroundings. The warm weather is perfect for outdoor adventures and enjoying the region’s natural beauty.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
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Winter (December to February)

The winter months bring a peaceful charm to the area, attracting visitors who enjoy a tranquil retreat and seasonal festivities. Expect colder temperatures conducive to cozy getaways and scenic winter views.

Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 30°F

Weekly Weather Forecast for Woodbury

How to Book Your Woodbury 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 Woodbury

More Top-Rated Vacation Rentals in Woodbury 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 a private outdoor space with a patio or deck to unwind and take in the fresh air.
  • Take advantage of a spacious backyard perfect for outdoor activities or barbecues.
  • Relax by a private or shared pool, ideal for cooling off during warm summer days.
  • Make use of outdoor dining areas designed for al fresco meals with family and friends.
  • Explore nearby scenic trails or nature walks directly accessible from the property.
  • Benefit from landscaped gardens or green spaces that enhance your outdoor experience.
  • Utilize outdoor recreational amenities such as a tennis court, basketball hoop, or fire pit, depending on the property.

Top Attractions Around Woodbury

What attractions are nearby?

In this area, you can enjoy a variety of outdoor activities and explore local parks, making your stay in Woodbury an enriching and memorable experience.

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Family Activities

  • Woodbury Commons Premium Outlets: Enjoy a family shopping spree at this popular outlet mall, offering a variety of brands and discounts for all ages.
  • Bear Mountain State Park: Experience outdoor adventures with scenic hiking trails, picnic areas, and beautiful views just a short drive from the area’s vacation rentals.
  • Hudson Highlands Cruises: Take a relaxing boat tour along the Hudson River to explore the region's natural beauty and enjoy memorable family moments.
  • Ringwood State Park: Discover the diverse recreational activities available here, including hiking, fishing, and exploring historic sites within easy reach of your stay.
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Adult Activities

  • Shopping at Woodbury Common Premium Outlets: Enjoy a premier retail experience just minutes from your accommodation, with an extensive selection of designer outlets offering exceptional deals.
  • Exploring Bear Mountain State Park: Immerse yourself in outdoor adventure by hiking, biking, or taking in the scenic views along the Hudson River within this popular regional park.
  • Visiting local wineries and breweries: Sample craft beverages at nearby vineyards and breweries, perfect for relaxing afternoons in the region's thriving beverage scene.
  • Playing a round at Thunder Ridge Ski Area: Experience year-round activities at this local ski resort, including snow sports during winter and mountain biking or zip-lining in warmer months.

Other Places to Stay in Woodbury, NY

Oyster Bay Golf Course
Oyster Bay Golf Course Vacation Rentals
More Places to Stay Near Woodbury

Woodbury Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local dining and shopping opportunities: Take advantage of nearby eateries and boutiques to immerse yourself in the area’s vibrant community and make your stay more memorable.
  • Plan outdoor activities: Utilize the region’s natural surroundings by scheduling outdoor adventures, which can enhance your vacation experience here.
  • Visit seasonal events and festivals: Check the local calendar for seasonal happenings that can provide authentic insights into the area's culture during your stay.
  • Choose a well-located vacation rental: Select accommodations with convenient access to key attractions and transportation options to maximize your time exploring this destination.

Transportation Options

  • Metro-North Railroad: This regional rail service provides convenient connections from the area to New York City and beyond, making it easy to explore nearby urban attractions.
  • Local Bus Services: Local bus routes serve the region, offering affordable transportation options for navigating around Woodbury and its surroundings.
  • Taxi and Ride-Sharing Services: Reliable taxi and ride-sharing options are available here, providing a flexible way to travel within the region and access key destinations effortlessly.
  • Private Car Rentals: Renting a private vehicle is a popular choice here for exploring the destination at your own pace, especially when staying in nearby vacation rentals.

Local Customs Options

  • Local Craftsmanship: You’ll notice a deep appreciation here for handcrafted goods, reflecting the area's rich tradition of artisanal work and local markets.
  • Seasonal Festivals: Participating in seasonal festivals allows you to experience the vibrant community spirit that is a cherished part of this region's culture.
  • Historical Preservation: Respect for history is evident through well-preserved landmarks that tell the story of this destination’s past and are often highlighted during local tours.
  • Community Dining Etiquette: Informal yet warm, the dining customs emphasize sharing and hospitality, giving you a genuine taste of the area's welcoming nature.

Frequently Asked Questions About Woodbury?

1. What are the top vacation rentals in Woodbury?

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

2. Which vacation homes in Woodbury are best for families?

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

3. How many Rentbyowner vacation rentals are available in Woodbury?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 41 in the Woodbury 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 Woodbury. 

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

Cancellation policies vary depending on the individual owner or property listing. It’s important to review the specific terms outlined in the listing details or contact the host directly before booking.

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

Additional fees such as cleaning, service charges, or security deposits may apply. These details are typically included in the listing description, but confirming with the owner ensures transparency before finalizing your reservation.

6. How do I ensure my stay will be secure and trustworthy?

Booking through reputable platforms that verify listings and provide customer support helps ensure a safe experience. Read reviews from previous guests and communicate directly with hosts for any specific concerns.

7. What amenities can I expect in vacation rentals around here?

Amenities vary by property, so it’s best to check each listing for details like Wi-Fi, parking, kitchen facilities, or other features important for your stay. Contact the host if you have specific requirements.

8. Is there a minimum stay requirement for bookings in this destination?

Minimum stay policies depend on the individual rental property. Review the listing's details or contact the owner to confirm the length of stay required during your planned visit.