Ossining holiday rentals

We found 204 holiday rentals — enter your dates for availability
Discover a selection of 8 homes and other holiday rentals in Ossining that are perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday rentals have the best amenities for spending time at your holiday home, which might include Wi-Fi and a pool. You're sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

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The natural setting of Ossining is ready to explore

The area's monuments and museums are just some of the reasons to come on holiday to Ossining. This city's restaurants, parks and golfing draw many visitors. Whether you're planning a family holiday, romantic stay or trip with friends, holiday 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 find top things to see and do while you're in the area? Venture out of your holiday home and check out everything that makes Ossining a fun spot to go on holiday. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Rockland Bakery (8.4 mi / 13.5 km)
  • New York Country Club (10.1 mi / 16.2 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)
  • Rye Playland (16.8 mi / 27 km)

Exploring the natural features in Ossining

Whether you're looking for adventure or just want to appreciate the scenery, Ossining is a great place to get out in nature. Here are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Tallman Mountain State Park (9.6 mi / 15.5 km)

How to get to and around Ossining

The nearest airport is in White Plains, NY (HPN-Westchester County), located 10.5 mi (16.8 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Teterboro, NJ (TEB), which is 23.9 mi (38.5 km) away.

If you'd rather travel by train, the main station is Ossining Station.

Frequently asked questions

What is the best area to stay in Ossining when booking a holiday rental?
When considering a holiday rental in Ossining, New York, the area around the downtown district is a fantastic choice. This vibrant neighbourhood boasts a lovely mix of historic charm and modern conveniences, making it an ideal spot for visitors. With a variety of properties available, you can find everything from quaint cottages to more contemporary apartments.The downtown area is particularly appealing due to its proximity to several attractions. The beautiful waterfront along the Hudson River offers stunning views and a lovely park where you can enjoy leisurely walks or picnics. Additionally, the renowned Sing Sing Prison Museum is a fascinating visit, providing insights into the local history and the infamous prison that operated for over a century.Moreover, the downtown's selection of restaurants and shops adds to the overall experience, allowing you to savour local cuisine and indulge in some retail therapy.
What is the most popular type of holiday rental accomodation in Ossining?
In Ossining, holiday houses are the most popular type of holiday rental, with about 15 available throughout the area. These properties typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and comfortable living areas, making them suitable for families or groups. Additionally, several cottages can be found, offering a more quaint and rustic charm. These cottages often include outdoor spaces for relaxation and enjoying the natural surroundings.
Are there any family house rentals in Ossining?
In Ossining, New York, there are several family-friendly house rentals available, making it a great choice for those travelling with children. The charming neighbourhoods here provide a variety of spacious homes equipped with essential amenities. Many properties feature large living areas, fully stocked kitchens for preparing family meals, and outdoor spaces where kids can enjoy playtime.Visitors will find that these accommodations often include conveniences such as Wi-Fi and air conditioning, ensuring a comfortable stay. Furthermore, the location offers proximity to parks and recreational areas, allowing families to explore the outdoors and engage in various activities.
Can I rent a holiday home with a pool or hot tub in Ossining?
In Ossining, there are several holiday homes available for rent that feature pools and hot tubs, making it an appealing choice for travellers seeking relaxation and comfort. This charming town along the Hudson River offers lovely views and a peaceful atmosphere, superb for a getaway. Many of the rentals come equipped with amenities such as private pools, outdoor entertaining areas, and fully equipped kitchens, ideal for families or groups looking to enjoy a leisurely stay. Additionally, some properties may include hot tubs, providing a superb spot to unwind after a day of exploration.
Are there pet-friendly house rentals in Ossining?
In Ossining, there are several pet-friendly house rentals available, making it a welcoming destination for travellers with pets. Many of these rentals offer amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, ideal for families or groups. The homes often feature modern conveniences like Wi-Fi and laundry facilities, ensuring a comfortable stay.The area is also conveniently located near parks and recreational spaces where pets can enjoy the outdoors. For instance, the scenic Teatown Lake Reservation offers hiking trails and beautiful views, superb for walks with pets. Additionally, the nearby Croton Point Park provides ample open space for pets to roam and play, enhancing the overall experience for pet owners.
Are there any remote work holiday rentals in Ossining?
In Ossining, New York, there are around 18 holiday rentals suitable for remote work. This charming town along the Hudson River offers a peaceful environment, ideal for those balancing work and leisure. Many properties come equipped with dedicated workspaces, including desks and chairs, ensuring a comfortable setup for productivity. High-speed internet and free Wi-Fi are commonly available, allowing for seamless connectivity.Ossining also boasts a picturesque riverside setting, with nearby parks and scenic views that can provide a refreshing break from work. The local area features delightful cafes and restaurants, superb for unwinding after a day of remote work. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Ossining?
In Ossining, popular rental amenities include kitchens, which allow guests to prepare their meals conveniently. Many properties also feature patios, offering outdoor spaces for relaxation and enjoying the fresh air. For entertainment, some rentals come equipped with arcade game rooms, providing fun for families and groups. Additionally, coffee and tea makers are commonly available, ensuring that guests can enjoy their favourite hot beverages at any time.
When is the best time to visit Ossining for a holiday rental?
The best time to visit Ossining for a holiday rental is during the peak season from July to September. This lively period attracts families and outdoor enthusiasts eager to enjoy the warm summer weather and the diverse activities available along the Hudson River. Visitors can partake in boating, hiking, and exploring the area's charming parks, all while soaking up the vibrant setting of the community.July stands out as the most popular month, where you'll find a bustling energy with numerous festivals and events taking place. The average temperatures during this time hover around 25 to 30 degrees Celsius, creating ideal conditions for outdoor fun and relaxation.If you're looking for a more budget-friendly option, consider visiting in December. This month offers a quieter charm, superb for cosy getaways and enjoying the festive holiday decorations without the crowds. While the temperatures dip to around 0 to 5 degrees Celsius, the picturesque winter scenery provides a beautiful backdrop for peaceful strolls and intimate gatherings.
What are the top attractions in Ossining?
In Ossining, visitors can explore several interesting attractions that highlight the town's rich history and natural beauty. The waterfront at Louis Engel Waterfront Park offers scenic views of the Hudson River, making it a lovely spot for leisurely walks and picnics. The nearby Ossining Historical Society Museum provides insight into the local history, showcasing artifacts and exhibits that reflect the town's past.For those who enjoy outdoor activities, the scenic trails at the nearby Teatown Lake Reservation are ideal for hiking and birdwatching, with opportunities to enjoy the area's natural wildlife and landscapes. Additionally, the Sing Sing Correctional Facility, although primarily a functioning prison, has a historical significance that can be explored through local tours that delve into its storied past.The charming downtown area features a variety of shops and eateries, giving visitors a taste of local culture and cuisine.
Are all fees included in the Ossining holiday homes prices shown on Stayz?
Stayz 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.
Are there any Ossining holiday homes with parking?
Stayz offers a wide selection of holiday homes in Ossining with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details 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.
Are there any discounts for Ossining holiday homes?
You can find great discounts on holiday homes in Ossining on Stayz, 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 change or cancel my Ossining holiday home booking on Stayz?
To find Ossining holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Ossining?
A long-stay holiday home in Ossining is the best way to experience local living. Plus, you can make the most of long-stay discounts. 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.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising 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 favourites, and build the perfect itinerary together.
How early should I book a Ossining holiday home?
Book your Ossining holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Ossining?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Ossining to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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