Ossining Accommodations

Hudson Valley Pool Retreat · 50min to NYC · 3 Acre

New

House

Hudson Valley Pool Retreat · 50min to NYC · 3 Acre

3 Bedrooms 1 Bath 6 Guests

US $552/Night 7 Nights - US $3,862

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Apartment

Croton Nook - Cozy Getaway

10.0

Exceptional

(2 Reviews)

1 Bedroom 1 Bath 3 Guests 602.78 ft²

US $245/Night 7 Nights - US $1,716

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House

Summer Pool Oasis Custom Bar Arcade Pool Table

1 Bedroom 1 Bath

US $1,595/Night 7 Nights - US $11,163

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New

Bed & Breakfast

Adorable 2-bedroom bed & breakfast in fantastic Ossining location

2 Bedrooms 1 Bath 4 Guests

US $255/Night 7 Nights - US $1,787

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Apartment

Croton Quarters - Comfortable Apartments, NYC close

9.9

Exceptional

(12 Reviews)

4 Bedrooms 2 Baths 8 Guests 974.13 ft²

US $283/Night 7 Nights - US $1,983

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House

Beautiful Brand New Private Duplex Unit in Lower Hudson Valley "Stone Haven"

10.0

Exceptional

(13 Reviews)

1 Bedroom 1 Bath 5 Guests

US $436/Night 7 Nights - US $3,050

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NYC-Area Escape Near River, Trails & MTA!

House

NYC-Area Escape Near River, Trails & MTA!

8.7

Fabulous

(3 Reviews)

5 Bedrooms 4 Baths 11 Guests 2798.62 ft²

US $689/Night 7 Nights - US $4,825

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'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

Price Dropped

Apartment

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

10.0

Exceptional

(6 Reviews)

2 Bedrooms 1 Bath 4 Guests 1200 ft²

US $476/Night 7 Nights - US $3,329

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Price Dropped

House

Neighbor's house - Welcome!

10.0

Exceptional

(5 Reviews)

2 Bedrooms 2 Baths 6 Guests

US $138/Night 7 Nights - US $967

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Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

Highly Rated

Apartment

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

9.8

Exceptional

(92 Reviews)

2 Bedrooms 1 Bath 4 Guests 800 ft²

US $413/Night 7 Nights - US $2,889

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Highly Rated

House

Cozy house on the Hudson

9.6

Exceptional

(73 Reviews)

1 Bedroom 1 Bath 2 Guests

US $409/Night 7 Nights - US $2,861

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Polished 1BR w/Accessible Room Features + Sauna

Price Dropped

Apartment

Polished 1BR w/Accessible Room Features + Sauna

6.0

Good

(1 Review)

1 Bedroom 1 Bath 2 Guests 210 ft²

US $275/Night 7 Nights - US $1,926

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More Top-Rated Accommodations in Ossining Area

Why Choose Rent By Owner for your Ossining Accommodations?

What makes our Accommodations 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 Accommodations stay?

To make the most of your visit, consider planning your vacation during the region's optimal seasons when the weather is most inviting and local events enhance your experience in Ossining, New York, USA.

Peak Season Highlights

Late Spring to Early Summer (May to June)

Experience the area's vibrant atmosphere with pleasant weather during this period, making it ideal for exploring local attractions and enjoying outdoor activities.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F

Early Fall (September to October)

Visit when the region's scenery is at its most stunning, with comfortable temperatures and fewer crowds, perfect for a peaceful getaway.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F

Off-Season Highlights

Winter (December to February)

During these months, you can enjoy more tranquil surroundings and potentially find better deals on accommodations while experiencing the quiet charm of the area.

Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 30°F

Late Fall (November to early December)

As the foliage changes and tourist numbers decrease, it's an excellent time to explore in a more relaxed setting with less competition for accommodations.

Average Temperature Daytime: 45°F to 55°F - Nighttime: 35°F to 45°F

Weekly Weather Forecast for Ossining

How to Book Your Ossining Accommodations

What's our booking process?

Our platform allows you to browse a curated selection of accommodations. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Ossining

More Top-Rated Accommodations in Ossining Area

Common Accommodations Amenities

What amenities can you expect?

Our Accommodations 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 setups perfect for relaxing meals amidst scenic views.
Get access to spacious yards or gardens ideal for outdoor activities and leisure.
Take advantage of private patios or decks to unwind and soak in the surroundings.
Benefit from outdoor grilling areas to enhance your culinary experience during your stay.
Relax in inviting outdoor seating areas designed for socializing and enjoying nature.
Explore well-maintained walking paths or trails right on the property, perfect for outdoor excursions.
Make use of any available swimming pools or hot tubs to add a touch of luxury to your outdoor experience.

Top Attractions Around Ossining

What attractions are nearby?

During your stay, you can explore a variety of outdoor activities, cultural attractions, and scenic parks that highlight the best of Ossining, New York and its surrounding area, offering a memorable experience just moments from your chosen property.

Family Activities

Ossining Riverwalk Park Enjoy a family stroll along the scenic riverwalk, where you can take in beautiful views and participate in easy outdoor activities suitable for all ages.
Sing Sing Prison Museum Discover the history of this historic site with engaging exhibits that provide educational fun for older children and teenagers interested in local heritage.
Participate in nature hikes, birdwatching, and outdoor programs at this tranquil nature preserve, ideal for family adventure and exploration.
Ossining Historical Society Museum Explore the area's rich history through interactive exhibits and tours designed to captivate young minds and foster family learning experiences.

Adult Activities

Hudson Riverwalk Take a leisurely stroll along the scenic Hudson Riverwalk, where you can enjoy stunning views and a peaceful atmosphere in the region.
Ossining Historical Society Museum Explore local history and culture through engaging exhibits at this museum, perfect for enriching your visit to the area.
Teatown Lake Reservation Experience outdoor adventure with hiking, birdwatching, or simply relaxing in nature at this popular natural reserve nearby.
Westchester Broadway Theatre Enjoy an entertaining night of live performances and dinner theater in the heart of this vibrant arts scene here.

Other Places to Stay in Ossining, NY

Ossining Travel Tips

How Can You Make the Most of Your Stay?

Plan Your Visit During Off-Peak Seasons: Scheduling your stay outside of peak times can offer a more relaxed experience and better rates in this scenic area.
Explore Local Dining Options: Take advantage of the region's diverse eateries to enjoy authentic flavors without straying far from your chosen property.
Book in Advance: Securing your accommodations early ensures availability and access to the best properties here, especially during popular travel periods.
Utilize Local Transportation: Familiarize yourself with available transportation methods to easily explore the area’s attractions and hidden gems without hassle.

Transportation Options

Metro-North Railroad You can easily access the regional rail network that connects this area to New York City and surrounding suburbs, making commuting convenient.
Public Bus Services Local bus options provide affordable transportation around the region, allowing you to explore nearby attractions with ease.
Taxis and Rideshare Services Taxis and popular rideshare apps offer flexible and on-demand transportation, ideal for navigating the area comfortably.
Personal Vehicles Having a private car gives you the freedom to explore at your own pace and reach more remote destinations within the region.

Local Customs Options

Local Farmers Markets: Visiting the area's farmers markets allows you to experience the region’s commitment to fresh, locally-sourced produce and support local artisans.
Hudson River Traditions: Engaging in waterfront activities and observing local customs along the Hudson River provides insight into the region’s historical connection to this iconic waterway.
Community Festivals: Participating in seasonal festivals celebrates the area's cultural heritage and offers a chance to enjoy local music, food, and crafts.
Historical Preservation Practices: Respect for historic landmarks and buildings reflects the community's dedication to maintaining its rich history and architectural integrity.

Frequently Asked Questions about Ossining Accommodations

1. What are the top Accommodations 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 Accommodations in Ossining:

2. How many Accommodations are available in Ossining?

Currently, the total number of properties listed by RBO in 2026 is over 28 in the Ossining area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Accommodations in Ossining. 

3. What is the cancellation policy for stays in Ossining accommodations?

The cancellation policies vary depending on the property listing. You should review the specific terms and conditions on the listing page or contact the property owner directly to understand any fees or restrictions related to cancellations.

4. Are there any specific check-in and check-out times I should be aware of in this region?

Check-in and check-out times are set by each property owner. It's recommended to verify these details during the booking process or contact the host directly to ensure a smooth arrival and departure experience.

5. How do I find accommodations that are suitable for my travel needs in this area?

You can filter your search based on amenities, property types, and location preferences to find accommodations that match your specific needs. For additional guidance, reaching out to the property owners can provide personalized recommendations.

6. Is Wi-Fi available at the properties in this destination?

Most accommodations in the region offer Wi-Fi; however, it’s best to confirm this feature on the listing page or by contacting the owner directly to ensure it meets your requirements.

7. What should I know about local rules and regulations when booking an accommodation here?

Local rules and regulations may vary by property. Carefully review the property description and house rules presented in the listing or consult with the owner for any specific guidelines to ensure a comfortable stay.