Ossining, NY Cottage Rentals

Ossining Cottage Rentals

Ossining Vacation Rental Near River, Trails & Mta!

Cottage

Ossining Vacation Rental Near River, Trails & Mta!

1 Bedroom 1 Bath

US $882/Night 7 Nights - US $6,177

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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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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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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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Hotel

Windrose on Hudson

7.1

Very Good

(57 Reviews)

4 Baths 215.28 ft²

US $284/Night 7 Nights - US $1,989

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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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House

Near NYC! | Stylish Guestroom

1 Bedroom 1 Bath 4 Guests 210 ft²

US $320/Night 7 Nights - US $2,237

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1BR Queen near NYC | Trails, Biking & Sauna Bliss

Price Dropped

Apartment

1BR Queen near NYC | Trails, Biking & Sauna Bliss

1 Bedroom 1 Bath 2 Guests 210 ft²

US $256/Night 7 Nights - US $1,793

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Hotel

2 Double Rooms | Cozy Escape with Convenient Access to Downtown Spots

2 Baths

US $522/Night 7 Nights - US $3,657

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Hotel

Relaxing Hudson Valley Stay | 2 Relaxing Units | Ossining, NY Views

2 Baths

US $481/Night 7 Nights - US $3,368

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More Top-Rated Cottage Rentals in Ossining Area

Why Choose Rent By Owner for your Ossining Cottage Rentals?

What makes our Cottage 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 Cottage Rentals stay?

Finding the ideal time to visit this destination can help you enjoy its natural beauty and peaceful atmosphere, making your stay in the area even more memorable and stress-free.

Peak Season Highlights

Spring (March to May)

During spring, you can enjoy the region's lush landscapes and mild weather, making it an ideal time to relax in a cozy cottage here.

Average Temperature Daytime: 55-70°F - Nighttime: 40-50°F

Summer (June to August)

The summer months bring warm weather perfect for enjoying outdoor activities around this destination’s scenic surroundings.

Average Temperature Daytime: 75-85°F - Nighttime: 60-65°F

Off-Season Highlights

Fall (September to November)

Visit during fall to experience the region's vibrant foliage while avoiding larger crowds and securing more affordable accommodations.

Average Temperature Daytime: 60-70°F - Nighttime: 45-55°F

Winter (December to February)

Winter offers a peaceful retreat with fewer visitors, perfect for those seeking a quiet getaway in a warm cottage setting.

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

Weekly Weather Forecast for Ossining

How to Book Your Ossining Cottage Rentals

What's our booking process?

Our platform allows you to browse a curated selection of cottage rentals. 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 Cottage Rentals in Ossining Area

Common Cottage Rentals Amenities

What amenities can you expect?

Our Cottage 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 seating areas such as patios or decks to relax and take in the scenic surroundings.
Take advantage of private gardens or landscaped yards for peaceful outdoor strolls.
Make use of barbecue grills and outdoor dining setups for al fresco meals with family or friends.
Explore access to nearby fire pits or outdoor fireplaces for cozy evenings under the stars.
Benefit from well-maintained walkways or paved paths around the property for leisurely walks or jogging.
Utilize outdoor recreational equipment like bikes, kayaks, or paddleboards available on-site or nearby.
Gain comfort from covered porches or verandas that offer shaded outdoor spaces to unwind during warmer days.

Top Attractions Around Ossining

What attractions are nearby?

While staying in this charming area, you can enjoy a variety of outdoor activities, explore scenic parks, or discover local cultural sites, making it an ideal destination for relaxation and adventure in Ossining, New York.

Family Activities

Ossining Waterfront Park Enjoy a family-friendly day outdoors with scenic views and playgrounds at this popular park along the Hudson River.
Sing Sing Prison Museum Discover the region's history through engaging exhibits that offer an educational experience suitable for the whole family.
Take a leisurely walk or bike ride along this historic trail, perfect for exploring the natural beauty of the area with loved ones.
Blue Oak Café & Play Area Combine a relaxed meal with some playtime as children can enjoy the dedicated play zone in this local café.

Adult Activities

Visiting the Ossining Waterfront Park: Enjoy a relaxing day by the river, perfect for picnicking, walking along scenic trails, or simply unwinding with picturesque views of the Hudson River.
Exploring historical landmarks at the Sing Sing Prison Museum: Gain insight into local history and the region’s fascinating past through engaging exhibits located just outside the town’s center.
Taking a guided tour of the Teatown Lake Reservation: Discover the natural beauty of this expansive nature preserve, ideal for birdwatching, wildlife observation, and light outdoor activities.
Dining at local eateries in the downtown area: Experience regional flavors and contemporary cuisine at charming restaurants that showcase the area's culinary diversity.

Other Places to Stay in Ossining, NY

Ossining Travel Tips

How Can You Make the Most of Your Stay?

Plan Your Stay in Advance: Booking your cottages early ensures you secure the ideal location and amenities to enhance your experience here.
Explore Local Cuisine and Markets: Take time to enjoy regional flavors and fresh produce, offering a true taste of the area's vibrant culinary scene.
Utilize Nearby Trails and Outdoor Spaces: Make the most of this destination's scenic natural surroundings by exploring nearby parks and walking paths during your visit.
Engage with Community Events: Check out local gatherings or cultural events that provide deeper insight into the region’s rich traditions and hospitality.

Transportation Options

Metro-North Railroad You can conveniently access commuter rail services connecting to New York City and other regional destinations, providing a reliable transport option from here.
Local Bus Services The area's local bus routes offer affordable and accessible transportation within the region, perfect for exploring nearby attractions and amenities.
Taxi and Rideshare Services Taxis and ridesharing options like Uber and Lyft are readily available, offering flexible and direct travel around here without the need for personal vehicle use.
Personal Vehicles Having a private car grants you the freedom to explore at your own pace, with parking options available near many accommodations in this part of the region.

Local Customs Options

Local Harvest Traditions: Participating in the region's farmers markets is a cherished custom where you can experience the community’s dedication to fresh, locally-sourced produce and handmade goods.
Historic Celebrations: The area celebrates its rich history through annual events that honor longstanding local customs, offering visitors a glimpse into the area's cultural heritage.
Community Festivals: Engaging in seasonal festivals allows you to enjoy traditional music, food, and crafts that reflect the vibrant local culture of this destination.
Religious Observances: Respect for local religious traditions is evident in the community's participation in customary ceremonies and holiday celebrations, fostering a sense of belonging and cultural appreciation.

Ossining Cottage Rentals Frequently Asked Questions

1. What are the top Cottages 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 Cottages in Ossining:

2. How many Cottages are available in Ossining?

Currently, the total number of properties listed by RBO in 2026 is over 1 in the Ossining area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in Ossining. 

3. What is the cancellation policy for cottages in Ossining, New York?

Cancellation policies vary by listing, so it’s important to review the specific terms listed on each property page. For detailed information, please check the cancellation policy before booking or contact the property owner directly.

4. Are there any additional fees I should be aware of when booking a cottage here?

Additional fees such as cleaning charges, service fees, or taxes may apply depending on the property. Details about any extra costs are usually provided during the booking process or in the listing description, so reviewing those details will ensure you’re fully informed.

5. What amenities are typically included with cottages in this area?

Most cottages offer essential amenities like Wi-Fi, parking, and kitchen facilities. To find out about specific features available at your preferred property, please read the listing description carefully or contact the owner for clarification.

6. Is there a minimum stay requirement for cottages in this region?

Minimum stay requirements can differ between properties. These details are generally specified on the listing page, so it’s advisable to confirm the length of stay before completing your reservation.

7. How do I contact the property owner if I have special requests or questions?

You can reach out to the property owner through the messaging system provided on the booking platform. For urgent or specific inquiries, it’s best to communicate your needs early to ensure a smooth experience.