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Woodbury vacation rentals

We found 272 vacation rentals — enter your dates for availability

Scroll through and select from vacation rentals in Woodbury to find one that's perfect for your trip. Whether you're traveling with a group or just with your pet, vacation rentals have the amenities you need and want for your stay, including WiFi and parking. No matter what you're looking for, you'll be sure to find a rental that has what everyone needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Woodbury

Showing deals for:May 8 - May 15

Image gallery for Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Outdoor spa tub
9.8 out of 10, Exceptional, (34 reviews)
Exceptional
(34 reviews)

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Greenwood Lake

8% off
Price is $410
$2,872 for 7 nights
All fees included
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

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Find out more about Woodbury

Why visit Woodbury

  • Outdoor Adventures: Enjoy camping and exploring the beauty of local state parks and serene lakes.
  • Family-Friendly Atmosphere: Woodbury offers a welcoming vibe perfect for family vacations and bonding activities.
  • Diverse Accommodation: Choose from cozy cabins, stylish condos, and comfortable apartments for your stay.
  • Urban and Cultural Exploration: Experience a mix of urban parks and cultural attractions throughout the area.
  • Memorable Getaways: Woodbury is an ideal location for both relaxation and adventure, creating lasting memories.

Popular types of accommodation in Woodbury

If you’re looking for the perfect getaway in Woodbury, you’re in the right place. Our most popular vacation rental options include cozy houses, stylish condos, and comfortable apartments. Whether you’re interested in woodbury cabin rentals, house rentals, or luxurious villa rentals, we have a variety of choices to suit your needs. Discover the ideal vacation home that offers both relaxation and adventure in beautiful Woodbury.

  • Houses: The top choice for vacationers in Woodbury, these homes offer spacious accommodations ideal for families or groups seeking comfort and privacy.
  • Condos: A popular selection, condos provide modern amenities and convenient locations, perfect for those wanting a blend of home and hotel experience.
  • Apartments: These versatile options are favored by travelers seeking a home-like atmosphere with easy access to local attractions.
  • Cottages: Quaint and cozy, cottages offer a charming getaway, perfect for a romantic retreat or peaceful escape.
  • Cabins: For nature enthusiasts, cabins provide a rustic and tranquil setting amidst the beautiful landscapes of Woodbury.**

Top attractions near Woodbury

Woodbury, located in Orange County, New York, is an ideal destination for family vacations, business trips, and urban exploration. Visitors can enjoy a variety of attractions, including urban parks, state parks, and serene lakes, all offering rich cultural and outdoor experiences. For those seeking adventure, the local campgrounds provide excellent options for camping and enjoying nature. Woodbury has something to offer for everyone looking to create lasting memories.

  • United States Military Academy: A prestigious institution located 6 miles from Woodbury, it offers a glimpse into military training and heritage. Visitors can explore historical buildings and scenic views along the Hudson River.
  • Bear Mountain State Park: Situated 7 miles away, this park features stunning landscapes, hiking trails, and outdoor activities. Perfect for nature lovers seeking adventure and picturesque scenery.
  • Storm King Art Center: Located 5 miles from Woodbury, this expansive outdoor sculpture park blends art and nature, providing a serene atmosphere and cultural vibes for art enthusiasts.

Things to do recommended for couples

For a romantic getaway in Woodbury, explore Brotherhood Winery for a cozy tasting experience, indulge in luxury at The Golf Club at Mansion Ridge, or hit the slopes together at Mount Peter Ski Area. Each offers unique vibes perfect for couples seeking adventure and intimacy.

Things to do recommended for families

During your family trip to Woodbury, enjoy thrilling sports at Michie Stadium, have fun at the Castle Fun Center's arcade, and make a splash at SplashDown Beach waterpark. Each attraction offers a unique mix of adventure and family-friendly vibes, perfect for creating lasting memories together.

Things to do recommended for groups

In Woodbury, groups can shop at the Woodbury Common Premium Outlets for a vibrant retail experience, enjoy a day of sports at the West Point Golf Course nearby, or catch a show at the Paramount Hudson Valley Theater for a touch of culture and entertainment.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Woodbury

If you're traveling with a group, family, pets, or planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Woodbury with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Woodbury with young kids: Traveling with little ones can be a bit tricky. It’s important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, thinking about how close you are to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Woodbury: For many families, a trip just isn't the same without their furry companion. If you can relate, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and cozy beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Woodbury: If you're searching for vacation rentals with discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Woodbury

Woodbury, nestled in Orange County, New York, offers an ideal vacation experience for families and business travelers alike. With its friendly atmosphere and opportunities for adventure, visitors can explore the beauty of Woodbury and enjoy a relaxing getaway. Nearby cities and neighborhoods enhance the experience with family-friendly vibes and romantic settings, making it the perfect destination for a memorable retreat. Discover the charm of Woodbury and create lasting memories on your vacation.

  • Newburgh: Situated 11 miles from Woodbury, Newburgh is a vibrant city rich in history and culture. Known for its family-friendly atmosphere, this city offers a delightful mix of outdoor activities and urban experiences. Visitors can explore the scenic waterfront along the Hudson River, enjoy shopping at various centers, and learn about local history at the visitor center. Notable attractions include lush parks and historic sites that provide a glimpse into the area’s past, making Newburgh a perfect day trip destination.
  • Beacon: Located 12 miles from Woodbury, Beacon is an inviting city that combines outdoor adventure with family fun. Nestled against the backdrop of stunning mountains, this city is ideal for nature lovers and thrill-seekers alike. Beacon’s attractions include hiking trails, a renowned theater scene, and opportunities for skiing in the winter months. Visitors can unwind in the picturesque parks or enjoy the serene lakes that dot the landscape, making it a charming spot to explore.
  • Goshen: Just 12 miles away from Woodbury, Goshen is a lively city known for its entertainment and family-friendly attractions. This city boasts shopping centers and a variety of resorts that cater to all ages. One of its main highlights is the nearby theme park, which offers thrilling rides and activities for the whole family. The modern square and bustling tourist precinct provide a vibrant atmosphere to explore local shops and restaurants, ensuring a fun-filled visit.

Best time to go to Woodbury

If you're planning a trip to Woodbury, it's a good idea to check both the weather and property rates. The warmest months are July and July. Peak season runs in July, July, September, September, November and November, while off-peak times, like January, January to February, February, October and October tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January27.9°F (-2.3°C)Light RainMostly SunnySlightly LowAverage
January27.9°F (-2.3°C)Light RainMostly SunnySlightly LowAverage
February29.8°F (-1.2°C)Light RainMostly SunnySlightly LowSlightly Low
February29.8°F (-1.2°C)Light RainMostly SunnySlightly LowSlightly Low
March37.4°F (3.0°C)Light RainMostly SunnyAverageSlightly Low
March37.4°F (3.0°C)Light RainMostly SunnyAverageSlightly Low
April48.7°F (9.3°C)Light RainMostly SunnyAverageSlightly Low
April48.7°F (9.3°C)Light RainMostly SunnyAverageSlightly Low
May59.4°F (15.2°C)Light RainMostly SunnyAverageAverage
May59.4°F (15.2°C)Light RainMostly SunnyAverageAverage
June67.6°F (19.8°C)Light RainMostly SunnyAverageAverage
June67.6°F (19.8°C)Light RainMostly SunnyAverageAverage
July73.9°F (23.3°C)Light RainMostly SunnySlightly HighSlightly High
July73.9°F (23.3°C)Light RainMostly SunnySlightly HighSlightly High
August72.0°F (22.2°C)Light RainMostly SunnyAverageSlightly High
August72.0°F (22.2°C)Light RainMostly SunnyAverageSlightly High
September64.9°F (18.3°C)Light RainMostly SunnySlightly HighAverage
September64.9°F (18.3°C)Light RainMostly SunnySlightly HighAverage
October54.0°F (12.2°C)Light RainMostly SunnySlightly LowAverage
October54.0°F (12.2°C)Light RainMostly SunnySlightly LowAverage
November42.1°F (5.6°C)Light RainMostly SunnySlightly HighAverage
November42.1°F (5.6°C)Light RainMostly SunnySlightly HighAverage
December34.2°F (1.2°C)Light RainMostly SunnyAverageSlightly High
December34.2°F (1.2°C)Light RainMostly SunnyAverageSlightly High

Booking with Vrbo is a breeze

Are you hoping to cut costs on your next getaway? Being flexible with your travel dates can really help, as prices tend to vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Unlock savings with One Key

When you reserve an eligible Vrbo for your group getaway, you’ll receive OneKeyCash on the full booking amount. Being the organizer truly has its benefits. Enroll in our OneKey rewards program to unlock exclusive savings and earn OneKeyCash on qualifying stays. Sign up today and begin earning rewards.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly platform where you can easily create new trips, resume your planning, or manage your current travel arrangements. You’ll find your saved or booked properties neatly organized into categories like Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Why people love visiting friendly Woodbury

The lake, mountains and forests display a scene truly unique to Woodbury. This welcoming city is known for its shopping, hiking and coffeehouses. With a vacation rental, you get a home away from home. Many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in and around Woodbury

Are you looking for things to do in the area? Venture out of your vacation home and experience everything that makes Woodbury a fun spot to vacation. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Brotherhood Winery (5.5 mi / 8.9 km)
  • LEGOLAND® New York (10.7 mi / 17.3 km)
  • Ice Time Sports Complex (10.9 mi / 17.6 km)
  • Mount Peter Ski Area (12.7 mi / 20.4 km)
  • SplashDown Beach (16.4 mi / 26.3 km)
  • Benmarl Vineyards and Winery (17 mi / 27.4 km)

Exploring the natural features in Woodbury

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Woodbury is a great place to get out in nature. These are some of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city center:

  • Storm King Art Center (4.8 mi / 7.8 km)
  • Arrow Park Lake and Lodge (6.6 mi / 10.6 km)
  • Storm King State Park (7.1 mi / 11.4 km)
  • The Rock Sports Complex (9 mi / 14.4 km)
  • Lake Welch Beach (9.2 mi / 14.8 km)
  • Boscobel House and Gardens (9.3 mi / 15 km)

Traveling to and around Woodbury

Fly into Stewart Intl. Airport (SWF), the closest airport, located 9.4 mi (15.1 km) from the city center. If you can't find a flight that's convenient for your trip, you could also fly into Westchester County Airport (HPN), which is 29.2 mi (47 km) away.

If you prefer train travel, the main station serving the city is Harriman Station.

Frequently asked questions

What is the best area to stay in Woodbury when booking a vacation rental?
When considering a vacation rental in Woodbury, New York, a popular area to stay is near the Woodbury Common Premium Outlets. This location not only offers a fantastic shopping experience with over 200 stores, including high-end brands, but it also provides easy access to various dining options and entertainment venues. Additionally, this area is well-connected to major roads, making it convenient for exploring the surrounding region.

Another excellent neighborhood to consider is the scenic vicinity of the Woodbury Nature Preserve. This area is superb for nature enthusiasts, with beautiful hiking trails and opportunities for birdwatching. The preserve offers a tranquil environment, allowing visitors to unwind and experience the natural beauty of the region. In terms of vacation rentals, you'll find a diverse selection of properties in both of these areas, ranging from cozy homes to spacious rooms.

Staying in Woodbury not only immerses you in a vibrant shopping and nature experience but also places you within easy reach of nearby attractions like the historic town of Cold Spring, known for its charming Main Street, and the stunning views along the Hudson River.
How much does it cost to rent a vacation home in Woodbury?
Prices for vacation rentals in Woodbury vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Woodbury to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Woodbury vacation house rentals?
You can find great discounts on house rentals in Woodbury on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I find long-stay vacation rentals in Woodbury?
A long-stay vacation rental in Woodbury is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there any Woodbury vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Woodbury with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
How early should I book a Woodbury vacation rental?
Book your Woodbury vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Woodbury?
In Woodbury, visitors can explore several attractions that cater to various interests. The Woodbury Common Premium Outlets is a major draw, offering a vast selection of designer and brand-name stores for those looking to indulge in some shopping. This area often attracts visitors seeking vacation rentals nearby for easy access to the outlets.

For outdoor enthusiasts, the nearby Oyster Bay Nature Preserve provides scenic walking trails and opportunities for birdwatching, making it ideal for those who appreciate nature. Families can also enjoy the Woodbury Recreation and Park District, which features playgrounds, sports facilities, and picnic areas, superb for a day of outdoor fun.

Additionally, the historic Woodbury House, which is a part of the local heritage, offers a glimpse into the area's past and can be an interesting stop for those interested in history and culture.
Can I change or cancel my Woodbury home rental booking on Vrbo?
To find Woodbury vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Woodbury vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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