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Ossining vacation rentals

We found 224 vacation rentals — enter your dates for availability

Discover a selection of 8 homes and other vacation rentals in Ossining that are perfect for your trip. Whether you’re traveling with friends, family, or just with your pet, vacation rentals have the amenities you expect for your stay, which might include parking and a washer and dryer. You'll be sure to find a rental that has what everyone needs, including options that are accessible or non-smoking.

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Find out more about Ossining

Why visit Ossining

  • Outdoor Adventures: Ossining boasts beautiful nature preserves and urban parks, perfect for hiking and exploring.
  • Ossining Farmers Market: A vibrant market showcasing local produce and artisan goods, ideal for a taste of the community.
  • Family-Friendly Activities: Numerous attractions cater to families, ensuring fun for visitors of all ages.
  • Charming Travelers Rest: A cozy spot to relax and unwind after a day of exploration.
  • Convenient Accommodations: A variety of vacation rentals and hotels provide comfortable stays close to attractions.

Popular types of accommodation in Ossining

Discover the charm of Ossining, NY, with our selection of vacation rentals. Whether you prefer cozy apartments, spacious houses, or modern condos, we have the perfect accommodation for you. Many travelers choose to stay in Ossining for its convenient access to nearby attractions and select hotels. Explore hotels near Ossining for additional options and enjoy a memorable getaway filled with transparency, savings, and reassurance.

  • Apartments: The top choice for travelers to Ossining, offering a comfortable and convenient stay with amenities like kitchens and living spaces.
  • Houses: A popular option for families and groups, these homes provide a home-like atmosphere with privacy and space.
  • Condos: Ideal for those seeking a blend of hotel-like amenities and home comforts, condos offer great locations and facilities.
  • Cottages: A charming choice for a cozy getaway, perfect for couples or small families wanting a quaint experience.
  • Cabins: For nature enthusiasts, cabins provide a rustic escape with access to outdoor adventures.**

Top attractions in Ossining

Ossining, New York, offers a wonderful blend of outdoor and family-friendly activities perfect for a city-themed vacation. Visitors can explore various points of interest, including medical centers, nature preserves, and urban parks. With its diverse attractions, Ossining is ideal for travelers seeking cultural experiences, outdoor adventures, and quality family time, ensuring there's something for everyone to enjoy during their stay.

  • Sing Sing Correctional Facility: This historic prison, located in Ossining, offers a unique glimpse into the past of the American correctional system. Known for its architectural significance and cultural history, it evokes a deep sense of reflection on justice and rehabilitation.
  • Sing Sing Prison Museum: Situated within the grounds of the former prison, this museum provides fascinating insights into the lives of inmates and the prison's history, complete with exhibits that educate visitors on the American penal system.
  • Thomas J. Watson Research Center: A family-friendly research facility, this center is known for its innovative technology and friendly atmosphere, making it an intriguing spot for visitors interested in the intersections of science and everyday life.

Things to do recommended for couples

Planning a romantic getaway in Ossining? Enjoy the luxury vibes at The Golf Club at Mansion Ridge, just 19 miles away, or indulge in a day at the Greenwich Polo Club, located 12 miles from town. Both offer unforgettable experiences for couples seeking a special time together.

Things to do recommended for families

Families will love exploring the scenic trails at the nearby Teatown Lake Reservation, where kids can learn about nature. A visit to the Ossining Historical Society Museum provides a fun glimpse into local history, while the waterfront park offers playgrounds and picnic spots for a perfect day out.

Things to do recommended for groups

Explore the scenic waterfront at Louis Engel Park or take a guided tour of the historic Ossining Correctional Facility. Enjoy a group hike at the nearby Croton Point Park, offering beautiful views of the Hudson River and fun picnic spots for everyone to relax together.

*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 Ossining

When planning your trip—whether you're traveling with a group, enjoying a family vacation, bringing along your pets, or seeking extended stays—it's important to prioritize your preferences. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Ossining 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 many more on Vrbo.
  • Traveling to Ossining with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with ensuring access to suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Ossining: For many families, a trip isn’t truly finished without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Ossining: If you’re in search of vacation rentals that offer 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 criteria as well.

Where to stay in and around Ossining

Ossining, New York, offers a delightful blend of outdoor adventures and family-friendly experiences. Explore the vibrant Ossining Farmers Market, where local produce and artisan goods abound. Don't miss the charming Travelers Rest, a great spot to unwind after a day of exploration. Nearby cities provide a romantic and relaxing atmosphere, making Ossining an ideal base for your vacation. Enjoy the friendly vibes and diverse activities that this lovely region has to offer.

  • Crotonville: Nestled in the picturesque landscape of Ossining, Crotonville is a charming village that invites outdoor enthusiasts and adventure seekers alike. The area boasts stunning scenery, with nearby mountain ranges and nature reserves perfect for hiking and exploring. Visitors can enjoy recreational activities in local parks and visit a variety of shopping centers and malls. The proximity to national and state parks offers ample opportunities for nature lovers to immerse themselves in the region's natural beauty.
  • Briarcliff Manor: Just 2 miles from Ossining, Briarcliff Manor is a vibrant city known for its family-friendly atmosphere and outdoor attractions. The area features several shopping venues, including bustling shopping centers and quaint boutiques. Briarcliff Manor also boasts community spaces like modern squares and tourist precincts, perfect for leisurely strolls and social gatherings. With its blend of urban charm and green spaces, this city offers a delightful experience for visitors seeking both excitement and relaxation.
  • Rockland Lake: Located 3 miles from Ossining, Rockland Lake is a serene village renowned for its romantic ambiance and outdoor activities. The centerpiece of this area is the beautiful lake, where visitors can unwind at the beach or engage in water sports. Golf enthusiasts will appreciate the local golf courses that provide scenic views and challenging play. With its proximity to national state parks, Rockland Lake offers an ideal escape for couples and nature lovers looking to connect with the outdoors.

Best time to go to Ossining

If you're planning a trip to Ossining, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April, July and September, while off-peak times, like December to February tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January30.0°F (-1.1°C)Light RainMostly SunnySlightly LowSlightly Low
February31.6°F (-0.2°C)Light RainMostly SunnySlightly LowSlightly Low
March38.8°F (3.8°C)Light RainMostly SunnyAverageSlightly Low
April49.8°F (9.9°C)Light RainMostly SunnySlightly HighAverage
May60.1°F (15.6°C)Light RainMostly SunnyAverageAverage
June68.9°F (20.5°C)Light RainMostly SunnyAverageAverage
July75.6°F (24.2°C)Light RainMostly SunnySlightly HighSlightly High
August73.9°F (23.3°C)Light RainMostly SunnyAverageSlightly High
September66.9°F (19.4°C)Light RainMostly SunnySlightly HighAverage
October56.1°F (13.4°C)Light RainMostly SunnyAverageAverage
November44.2°F (6.8°C)Light RainMostly SunnyAverageAverage
December36.3°F (2.4°C)Light RainMostly SunnySlightly LowSlightly High

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming trip? Keeping your travel dates flexible can really help, as prices can change. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the best options.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers an easy-to-use platform where you can create new trips, resume planning from where you last stopped, or manage and organize your travel plans. You'll see the properties you've saved or booked neatly sorted into categories: Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

The natural setting of Ossining is ready to explore

The area's monuments and museums are just a few of the reasons to vacation in Ossining. This city's restaurants, parks and golfing draw many visitors. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in and around Ossining

Do you want to discover things to do during your stay? Venture out of your vacation home and check out everything that makes Ossining a one-of-a-kind vacation spot. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Sportime USA (7 mi / 11.3 km)
  • New York Country Club (10.1 mi / 16.2 km)
  • Blue Hill Golf Course (10.1 mi / 16.3 km)
  • Legoland Discovery Center Westchester (13.6 mi / 21.9 km)
  • Haworth Country Club (15.8 mi / 25.5 km)
  • Putnam County Golf Course (16.4 mi / 26.4 km)

Exploring the natural features in Ossining

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Ossining is a great place to get outside. These are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:

  • Croton Point Park (2.2 mi / 3.5 km)
  • Nyack Beach State Park (4 mi / 6.4 km)
  • Rockefeller State Park Preserve (4 mi / 6.4 km)
  • Rockland Lake State Park (4 mi / 6.4 km)
  • Buttermilk Falls Park (6.9 mi / 11.1 km)
  • Blue Mountain Reservation (7.8 mi / 12.5 km)

How to get to and around Ossining

The nearest airport is in Westchester County Airport (HPN), located 10.5 mi (16.8 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly into Teterboro, NJ (TEB), which is 23.9 mi (38.5 km) away.

If you're traveling by train, the main station is Ossining Station.

Frequently asked questions

How much does it cost to rent a vacation home in Ossining?
Prices for vacation rentals in Ossining 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 Ossining 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 Ossining vacation house rentals?
You can find great discounts on house rentals in Ossining 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.
What is the most popular type of vacation rental accomodation in Ossining?
In Ossining, vacation houses and cottages are the most popular types of rental accommodations, with several available throughout the area. These properties are typically situated in charming neighborhoods, providing a serene environment for travelers. Most vacation houses come equipped with multiple bedrooms, fully stocked kitchens, and outdoor spaces such as patios or gardens, making them ideal for families or groups looking to enjoy a cozy feel. Similarly, cottages offer a cozy retreat with comfortable living areas and often scenic views of the surrounding landscape.
Are there any family house rentals in Ossining?
In Ossining, New York, families can find several vacation rentals that cater to their needs. The town offers a charming atmosphere with tree-lined streets and proximity to the scenic Hudson River. Many of these homes feature spacious living areas, full kitchens for preparing family meals, and outdoor spaces ideal for children to play. Amenities like Wi-Fi and air conditioning are typically included to ensure a comfortable stay.

For families eager to explore, the nearby Croton Point Park provides opportunities for picnicking, hiking, and enjoying beautiful river views. Additionally, the area's rich history can be appreciated at local sites such as the Ossining Historical Society Museum.
Can I rent a vacation home with a pool or hot tub in Ossining?
In Ossining, New York, there are several vacation homes available for rent that feature pools and hot tubs. This charming town, located along the Hudson River, offers a mix of natural beauty and suburban convenience. Many of the properties come equipped with private pools and hot tubs, providing an ideal setting for relaxation and recreation after a day of exploring the area.

Travelers can expect amenities such as spacious outdoor areas for lounging, fully equipped kitchens, and comfortable living spaces. Some rentals may also include barbecue grills and beautiful gardens, superb for family gatherings or socializing with friends.
Can I find long-stay vacation rentals in Ossining?
A long-stay vacation rental in Ossining 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 pet-friendly house rentals in Ossining?
In Ossining, there are several pet-friendly house rentals available, making it a great choice for travelers with furry companions. The area features charming homes that often come equipped with modern amenities such as fully stocked kitchens, spacious living rooms, and outdoor spaces like decks or gardens where pets can enjoy the fresh air.

Ossining itself is known for its scenic riverside views and proximity to parks, which offer excellent opportunities for outdoor activities with pets. The nearby Croton Point Park is a popular spot, featuring walking trails and open spaces for pets to roam. Additionally, the town's convenient access to the Hudson River provides beautiful waterfront areas for leisurely strolls.
Are there any remote work vacation rentals in Ossining?
In Ossining, New York, there are several vacation rentals available that cater to remote workers. The properties typically provide amenities such as free Wi-Fi, ensuring that guests can stay connected during their stay. Many rentals feature comfortable workspaces, allowing for a productive environment. Additionally, travelers can expect spacious living areas and well-equipped kitchens, making it easy to enjoy long-term stays. The town itself offers a charming atmosphere with nearby parks and the scenic Hudson River, making it a pleasant place to balance work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Ossining vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Ossining 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.
What are popular rental amenities in Ossining?
In Ossining, popular rental amenities include kitchens, which allow travelers to prepare their own meals conveniently. Many properties also feature outdoor spaces such as patios and decks, superb for enjoying the fresh air and relaxing after a day of exploring the area. For entertainment, some rentals come equipped with an arcade game room, providing fun activities for families or groups. Additionally, coffee and tea makers are commonly found in these rentals, ensuring guests can enjoy their favorite hot beverages at any time.
When is the best time to visit Ossining for a vacation rental?
July marks the peak season for visiting Ossining, New York, as travelers flock to the area to enjoy the warm summer weather and vibrant community activities. This month is particularly popular for outdoor enthusiasts, offering a superb blend of comfortable temperatures—typically in the mid-70s to low 80s Fahrenheit—and an array of local events. Visitors can take advantage of scenic walks along the Hudson River, explore the stunning waterfront parks, or participate in the lively summer festivals that showcase local art and culture.

As summer transitions into fall, the months of August and September also offer fantastic experiences, though July remains the highlight for those looking to soak up the sun and engage in community festivities. The warm temperatures create an inclusive setting for outdoor dining and sightseeing.

For travelers looking for a more budget-friendly option, December is an excellent time to visit Ossining. While it's outside the bustling summer season, the holiday charm of the area shines through. Visitors can enjoy the beautiful decorations, local holiday markets, and cozy winter activities. This quieter time of year allows for relaxed exploration of the scenic trails and historic sites without the crowds.
How early should I book a Ossining vacation rental?
Book your Ossining 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 Ossining, New York, United States of America?
In Ossining, visitors can explore several top attractions that highlight the town's charm and natural beauty. The historic Sing Sing Prison Museum offers a unique glimpse into the history of the infamous correctional facility, while the scenic waterfront along the Hudson River provides picturesque views and opportunities for leisurely strolls. Vacation rentals near the riverfront are ideal for enjoying outdoor activities like kayaking or simply relaxing by the water.

Ossining also boasts several parks, such as Louis Engel Waterfront Park, which features walking paths, picnic areas, and a playground, making it a great spot for families. Additionally, the nearby Croton Point Park offers hiking trails and access to the Croton River, superb for outdoor enthusiasts.
Can I change or cancel my Ossining home rental booking on Vrbo?
To find Ossining 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 Ossining 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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