Ossining Resorts
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 $556/Night
For 7 Nights US $3,894
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Ocean View
US $711/Night
For 7 Nights US $4,976
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
10 Guests
244 Bedrooms
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 $401/Night
For 7 Nights US $2,809
8 Guests
2 Bedrooms
2 Bathrooms
Hotel
- Spa
- Fireplace/Heating
- Pool
US $557/Night
For 7 Nights US $3,898
8 Guests
2 Bedrooms
2 Bathrooms
Hotel
- Spa
- Fireplace/Heating
- Pool
US $557/Night
For 7 Nights US $3,898
8 Guests
2 Bedrooms
2 Bathrooms
Hotel
- Spa
- Fireplace/Heating
- Pool
US $557/Night
For 7 Nights US $3,898
8 Guests
2 Bedrooms
2 Bathrooms
Hotel
- Spa
- Fireplace/Heating
- Pool
US $557/Night
For 7 Nights US $3,898
210 ft²
4 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Apartment
- Spa
- Fireplace/Heating
- Parking
US $400/Night
For 7 Nights US $2,797
210 ft²
2 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Apartment
- Spa
- Fireplace/Heating
- Parking
US $379/Night
For 7 Nights US $2,655
Why Choose Rent By Owner for your Ossining Resorts?
What makes our Resorts 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 Resorts stay?
Choosing the optimal time to vacation here in Ossining, New York, can enhance your experience by allowing you to enjoy favorable weather and local events, ensuring a memorable stay at the most desirable resorts in the region.
Peak Season Highlights
Summer (June to August)
During the peak summer months, you can experience warm temperatures ideal for outdoor activities in this area. It's the most popular time to visit, so expect lively surroundings and bustling resorts.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 70°F
Fall (September to November)
Autumn brings vibrant foliage and mild weather, making it a favorite season for visitors seeking scenic views and comfortable temperatures. Resorts tend to be lively with seasonal events during this period.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 50°F to 60°F
Off-Season Highlights
Winter (December to February)
The winter months offer quieter resorts and cooler temperatures, perfect if you prefer a more peaceful escape away from the crowds. It’s an ideal time for cozy stays and enjoying serene surroundings.
Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 30°F
Spring (March to May)
Springtime sees mild weather and blooming landscapes, providing a refreshing atmosphere for your stay. Resorts are less crowded, offering you a tranquil retreat in this region.
Average Temperature Daytime: 50°F to 65°F - Nighttime: 35°F to 45°F
Weekly Weather Forecast for Ossining
How to Book Your Ossining Resorts
What's our booking process?
Our platform allows you to browse a curated selection of resorts. 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 Resorts Amenities
What amenities can you expect?
Our Resorts 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 spacious outdoor swimming pool to relax and unwind during your stay.
- Take advantage of well-maintained private patios or decks perfect for outdoor dining or lounging.
- Explore beautifully landscaped gardens that offer a peaceful setting within the property grounds.
- Make use of outdoor grilling areas for a convenient and flavorful cookout experience.
- Relax in cozy outdoor fire pits, ideal for gathering with friends or family after a day of exploring.
- Discover scenic walking paths or trails surrounding the property, perfect for outdoor adventures in the region.
- Utilize dedicated outdoor recreational spaces such as sports courts or playgrounds for active entertainment.
Top Attractions Around Ossining
What attractions are nearby?
In this region, you can enjoy a variety of outdoor activities, cultural experiences, and natural attractions just a short drive from your chosen Ossining accommodation, making it an ideal destination for those looking to explore the scenic New York area while relaxing at comfortable resorts nearby.
Family Activities
- Peekskill Museum: Engage your family in local history with interactive exhibits and educational programs that bring the area's past to life.
Adult Activities
- Hudson River Cruises: Embark on a scenic cruise along the Hudson River to enjoy breathtaking views and a relaxing experience in this area.
- Vineyard Tours and Tastings: Explore local vineyards and indulge in wine tasting sessions that showcase the region's rich viticulture heritage.
- Historic Walking Tours: Discover the area's history and architecture through guided or self-led walking tours that highlight its cultural significance.
- Arts and Cultural Events: Attend art exhibits, live performances, and festivals that celebrate the vibrant arts scene in this destination.
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?
- Plan Ahead for Local Events: Research upcoming events in the region to align your stay with local festivals or activities, enhancing your experience.
- Explore Scenic Surroundings: Take advantage of nearby parks and natural attractions to enjoy the area's outdoor beauty during your visit.
- Utilize Local Transportation Options: Familiarize yourself with public transit or shuttle services in this destination to explore efficiently and comfortably.
- Book in Advance: Secure your preferred accommodations early to ensure availability and the best rates during peak seasons in this area.
Transportation Options
- Metro-North Railroad: This rail service offers convenient and reliable transportation from here to New York City and other nearby destinations, making it easy to explore the region without a car.
- Local Bus Services: The area's bus network provides budget-friendly and accessible options for traveling within Ossining and connecting to surrounding communities.
- Car Rentals: Renting a vehicle gives you the flexibility to explore further afield at your own pace, especially useful when staying in resorts in this part of New York.
- Taxi and Rideshare Services: On-demand taxis and rideshare options like Uber and Lyft are readily available, providing quick transportation around the area and to local attractions.
Local Customs Options
- Welcome Ceremonies: Local residents traditionally celebrate welcoming new neighbors and visitors with community gatherings that emphasize hospitality and friendship.
- Harvest Festivals: The region hosts annual harvest festivals that honor the area's agricultural roots through food, music, and local crafts.
- Religious Customs: Several local churches observe unique traditions during holidays and religious celebrations, reflecting the area's diverse spiritual heritage.
- Historical Commemorations: Residents take pride in commemorating regional history with annual events honoring significant figures and milestones of this destination.
Ossining Resorts Frequently Asked Questions
1. What are the top Resorts 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 Resorts in Ossining:
- Windrose On Hudson
- 4 Comfortable Double Rooms | Close to Waterfront Music, Events & Breweries
- 4 Comfortable Double Rooms | Close to Waterfront Music, Events & Breweries
- Relax in 4 Double Guestrooms Near Warren Street Shops & Waterfront Parks
- Close to Historic Sites, Markets & Local Wineries | 3 Comfortable Double Rooms
- Close to Art Studios & Hudson Nightlife | 3 Inviting Double Guestrooms
- Close to Art Studios & Hudson Nightlife | 3 Inviting Double Guestrooms
- Close to Historic Sites, Markets & Local Wineries | 3 Comfortable Double Rooms
- Family Friendly Resort with Fast Wi-Fi - Perfect for Spring Getaways
- 7BR Beacon Thanksgiving Foliage Game Room BBQ
2. How many Resorts are available in Ossining?
Currently, the total number of properties listed by RBO in 2026 is over 37 in the Ossining area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Resorts in Ossining.
3. What is the cancellation policy for resorts located in Ossining, New York?
Cancellation policies vary by property. You should review the specific resort listing details or contact the owner directly to understand the terms and any applicable fees before completing your reservation.
4. Are there any additional fees I should be aware of when booking a resort in this area?
Additional fees such as cleaning charges, resort fees, or taxes may apply. Please check the property's listing details or reach out to the owner for a complete breakdown of all costs involved.
5. How do I confirm my reservation at a resort in Ossining, New York?
Reservations are confirmed once you complete the booking process and receive a confirmation email from the platform. For any special requests or immediate confirmation needs, contact the property owner directly through the booking platform.
6. What amenities can I expect at resorts in this region?
Amenities vary by property but typically include features like Wi-Fi, swimming pools, on-site dining, or fitness centers. Detailed information about each resort’s amenities is available in the property listing, so review these before booking.
7. Is it possible to modify or cancel my booking if my plans change?
Modifications or cancellations depend on the individual resort’s policies. Refer to the listing details or contact the owner directly to understand your options and avoid any penalties.
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13 Guests
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- Private Pool
- Fireplace/Heating
- Pool
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11 Guests
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- Fireplace/Heating
- Balcony/Terrace
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- Fireplace/Heating
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