Best Vacation Homes in Ossining
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $198/Night
For 7 Nights US $1,383
2798.62 ft²
11 Guests
5 Bedrooms
4 Bathrooms
Free Cancellation
House
- Spa
- Fireplace/Heating
- View
US $689/Night
For 7 Nights US $4,825
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Ocean View
US $861/Night
For 7 Nights US $6,029
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $255/Night
For 7 Nights US $1,782
215.28 ft²
4 Bathrooms
Free Cancellation
Hotel
- Fireplace/Heating
- Balcony/Terrace
- View
US $263/Night
For 7 Nights US $1,839
210 ft²
2 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Apartment
- Spa
- Fireplace/Heating
- Parking
US $391/Night
For 7 Nights US $2,738
210 ft²
2 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Apartment
- Spa
- Fireplace/Heating
- Parking
US $364/Night
For 7 Nights US $2,551
210 ft²
4 Guests
1 Bedroom
1 Bathroom
Couples Retreat
House
- Spa
- Fireplace/Heating
- Parking
US $361/Night
For 7 Nights US $2,526
Ossining Luxury Rentals
1 Bedroom
1 Bathroom
Family Friendly
House
- Pool
- Balcony/Terrace
- Parking
US $1,111/Night
For 7 Nights US $7,777
4 Bathrooms
Group Friendly
Hotel
- Spa
- Fireplace/Heating
- Pool
US $1,079/Night
For 7 Nights US $7,554
4 Bathrooms
Group Friendly
Hotel
- Spa
- Fireplace/Heating
- Pool
US $1,079/Night
For 7 Nights US $7,554
4 Bathrooms
Group Friendly
Hotel
- Spa
- Fireplace/Heating
- Pool
US $1,067/Night
For 7 Nights US $7,469
4 Bathrooms
Group Friendly
Hotel
- Spa
- Fireplace/Heating
- Pool
US $1,067/Night
For 7 Nights US $7,469
4284 ft²
13 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
US $898/Night
For 7 Nights US $6,285
3 Bathrooms
Group Friendly
Hotel
- Spa
- Fireplace/Heating
- Pool
US $862/Night
For 7 Nights US $6,034
3 Bathrooms
Group Friendly
Hotel
- Spa
- Fireplace/Heating
- Pool
US $836/Night
For 7 Nights US $5,855
Ossining Pet Friendly Vacation Rentals
2800 ft²
11 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $696/Night
For 7 Nights US $4,875
6 Guests
3 Bedrooms
1 Bathroom
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
US $487/Night
For 7 Nights US $3,407
4300 ft²
13 Guests
7 Bedrooms
5 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Balcony/Terrace
US $1,295/Night
For 7 Nights US $9,065
1367 ft²
13 Guests
7 Bedrooms
4 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Balcony/Terrace
US $630/Night
For 7 Nights US $4,410
Ossining Top Rated Vacation Rentals
3 Bathrooms
Group Friendly
Hotel
- Spa
- Fireplace/Heating
- Pool
US $836/Night
For 7 Nights US $5,855
3 Bathrooms
Group Friendly
Hotel
- Spa
- Fireplace/Heating
- Pool
US $810/Night
For 7 Nights US $5,668
2 Bathrooms
Hotel
- Spa
- Fireplace/Heating
- Pool
US $570/Night
For 7 Nights US $3,991
2 Bathrooms
Hotel
- Spa
- Fireplace/Heating
- Pool
US $532/Night
For 7 Nights US $3,727
2 Bathrooms
Hotel
- Spa
- Fireplace/Heating
- Pool
US $532/Night
For 7 Nights US $3,727
2 Bathrooms
Hotel
- Spa
- Fireplace/Heating
- Pool
US $532/Night
For 7 Nights US $3,727
1 Bathroom
Couples Retreat
Hotel
- Spa
- Fireplace/Heating
- Pool
US $285/Night
For 7 Nights US $1,996
1 Bathroom
Couples Retreat
Hotel
- Spa
- Fireplace/Heating
- Pool
US $285/Night
For 7 Nights US $1,996
Why Choose Rent By Owner for your Ossining Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Ossining
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit can enhance your experience with this destination, allowing you to enjoy its attractions and local atmosphere at their best while booking the perfect vacation rentals in the area.
Peak Season Highlights
Summer (June to August)
During the warm summer months, you'll enjoy pleasant weather perfect for exploring the region's scenic outdoor spaces and local events.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 65°F
Fall (September to November)
Autumn offers vibrant foliage and mild temperatures, making it an ideal time to experience the area's natural beauty and cultural festivals.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 50°F to 55°F
Off-Season Highlights
Winter (December to February)
The quiet winter season provides a peaceful atmosphere with cooler temperatures, perfect for cozying up in your vacation rental and enjoying indoor activities.
Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 25°F
Spring (March to May)
Early spring sees fewer visitors, with blossoming trees and milder weather creating a lovely setting for exploring the region’s charms at a relaxed pace.
Average Temperature Daytime: 50°F to 60°F - Nighttime: 35°F to 45°F
Weekly Weather Forecast for Ossining
How to Book Your Ossining 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 Ossining
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 outdoor dining with a private patio or deck area to relax in the fresh air.
- Take advantage of a well-maintained backyard or garden space for outdoor activities or lounging.
- Make the most of scenic views from a spacious balcony or verandah that overlooks the region.
- Benefit from access to outdoor recreational facilities such as a swimming pool or tennis courts.
- Experience peaceful evenings around a cozy outdoor fire pit or barbecue area.
- Explore nearby walking trails or hiking paths that showcase the area's natural beauty.
- Utilize outdoor amenities like parking areas designed to accommodate RVs or boats, ideal for this destination.
Top Attractions Around Ossining
What attractions are nearby?
In this destination, you can explore a variety of outdoor activities and cultural attractions that showcase the charm and natural beauty of the region surrounding your vacation rentals.
Family Activities
- Ossining Historic Waterfront Walk: You can enjoy a family-friendly stroll along the scenic waterfront, taking in views of the Hudson River and exploring local parks.
This engaging museum offers hands-on exhibits that are perfect for children to learn and play together in the heart of the area. - Boscobel House and Gardens: Visiting this historic house provides an educational experience with its beautiful gardens and glimpse into regional history suitable for all ages.
Adult Activities
- Historic Walks and Tours: Explore the rich history of this destination through guided walking tours that highlight its unique heritage and architectural charm.
- Local Art Galleries and Studios: Visit nearby art galleries and studios to appreciate the vibrant creative scene that reflects the area's cultural essence.
- Fine Dining Experiences: Indulge in exceptional cuisine at acclaimed restaurants renowned for showcasing locally-sourced ingredients and regional flavors.
- Scenic Nature and Park Visits: Enjoy the tranquility of picturesque parks and scenic overlooks, perfect for relaxing or outdoor activities in the region.
Other Places to Stay in Ossining, NY
Maryknoll
Hudson Hills Golf Course
Kitchawan Preserve
Thomas J. Watson Research Center
Crotonville
Ossining Historical Society
Louis Engel Waterfront Park
Merchants Square
Pleasant Square
Sing Sing Prison Museum
Snowden Avenue Park
Depot Square
Ossining Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining Options: Take the opportunity to enjoy the region's culinary scene by visiting local eateries and cafes near your vacation rentals.
- Plan Outdoor Activities: Make the most of the area's natural beauty by scheduling outdoor adventures like hiking or strolling along scenic routes close to your stay.
- Visit Nearby Attractions Carefully: Prioritize must-see sites within easy reach to maximize your sightseeing without feeling rushed during your time here.
- Engage with the Community: Immerse yourself in the local culture by participating in community events or visiting markets near your accommodation.
Transportation Options
- Metro-North Railroad:** You can easily access commuter trains here, providing convenient travel to New York City and other parts of the region.
- Personal Vehicle:** Driving offers flexibility and direct routes, making it an ideal option for exploring the surrounding areas at your own pace.
- Bus Services:** Local and regional bus routes serve this destination, connecting you to nearby towns and transit hubs efficiently.
- Taxi and Rideshare Services:** On-demand taxis and rideshare options are readily available, offering a comfortable and quick way to get around within the area.
Local Customs Options
- Local Art and Craft Fairs: Participating in community art fairs is a cherished tradition here, showcasing the creative spirit of the area.
- Seasonal Harvest Celebrations: The region celebrates its agricultural roots with seasonal festivals that honor local harvests and culinary heritage.
- Historic Preservation Days: Residents take pride in maintaining the area's rich history through special events dedicated to preserving landmarks and heritage.
- Community Religious Festivals: Traditional religious festivals are observed with respectful gatherings that highlight local faith customs and practices.
Ossining Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Ossining?
There are a lot of options in Ossining. If you plan on staying in the Ossining area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Ossining:
- Neighbor's house - Welcome!
- Cozy house on the Hudson
- Castle Retreat w/Pool, BBQ, Game Room & Pets OK!
- NYC-Area Escape Near River, Trails and MTA!
- Windrose On Hudson
- NYC-Area Escape Near River, Trails & MTA!
- Windrose on Hudson
- Polished 1BR w/Accessible Room Features + Sauna
- Westchester Summer Pool Pet Friendly Events Games
- Relax in 4 Double Guestrooms Near Warren Street Shops & Waterfront Parks
2. How many vacation rentals have private pools in Ossining?
There are 1 vacation rentals with private pools near Ossining. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Ossining are best for families?
If you are looking for a family-friendly vacation home in Ossining, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Ossining:
4. How many Rentbyowner vacation rentals are available in Ossining?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 37 in the Ossining 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 Ossining.
5. What is the cancellation policy for vacation rentals in Ossining, New York?
Cancellation policies vary depending on the individual listing. To understand the specific terms, please review the cancellation policy outlined in the rental's details or contact the property owner directly.
6. How do I confirm a reservation for a vacation rental here?
You can confirm your reservation by completing the booking process through the rental listing. For additional assurance, reach out to the property owner if you have any questions before finalizing your booking.
7. Are there any house rules I should know before booking in this area?
House rules are set by each host and are detailed in the property listing. It's advisable to read these rules carefully before making a reservation to ensure your stay complies with the host's expectations.
8. What amenities are typically available in vacation rentals in this destination?
Amenities vary between properties, but many rentals here offer essentials like Wi-Fi, kitchen access, and parking. For specifics, always check the listing details or contact the owner directly.
9. Is local support available during my stay in this region's vacation rentals?
Support services depend on the individual property and host. Contact the host beforehand to clarify what assistance is available during your stay and ensure a smooth experience.
