Compare Ossining Vacation Rentals

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Ossining Rentals

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

0.45 mi from city center
$916 nightly
The price is $942 total per night
$942 total
Oct 5 - Oct 6
Total with taxes and fees
This vacation home offers a water park, an arcade/game room, and laundry facilities. Other amenities at this family-friendly vacation home include barbecue grills and a garden.
Pool
Kitchen
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven

Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven

2.71 mi from city center
This vacation home is a smoke-free vacation home.
Air conditioning
Global Luxury Suites White Plains

Global Luxury Suites White Plains

3.5 out of 5
57 Bank St, White Plains, NY
10.28 mi from city center
Global Luxury Suites White Plains features free WiFi in public areas, a 24-hour business center, and a seasonal outdoor pool. Valet parking is offered for USD 25 per day. Front-desk staff are standing by 24/7 to assist with any requests. Additional amenities include express check-out, laundry facilities, and barbecue grills.
Pool
Kitchen
Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic

Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic

10.49 mi from city center
$282 nightly
The price is $323 total per night
$323 total
Oct 5 - Oct 6
Total with taxes and fees
Guests staying at this vacation home have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

14.23 mi from city center
$272 nightly
The price is $308 total per night
$308 total
Sep 30 - Oct 1
Total with taxes and fees
Guests staying at this cottage have access to local meal delivery service, a garden, and barbecue grills.
Kitchen
Pet friendly
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

13.4 mi from city center
At this vacation home, guests have access to barbecue grills.
Kitchen
Free WiFi
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

14.5 mi from city center
$176 nightly
The price is $199 total per night
$199 total
Oct 6 - Oct 7
Total with taxes and fees
At this vacation home, guests have access to a garden.
Kitchen
Free WiFi
3BR Prime Luxury near NYC w Arcade Room

3BR Prime Luxury near NYC w Arcade Room

2 out of 5
50 Vernon Pl, Yonkers, NY
17.08 mi from city center
$687 nightly
The price is $769 total per night
$769 total
Sep 30 - Oct 1
Total with taxes and fees
At this vacation home, guests have access to free WiFi in public areas. A stay here includes free offsite parking. Dry cleaning/laundry services make packing light an option.
Washer
Dryer
Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking

3 out of 5
80 Woodlawn Ave, Yonkers, NY
17.72 mi from city center
Guests of this vacation home enjoy features like a rooftop terrace. You can take advantage of free parking if you drive.
Kitchen
Parking included
Stamford Suites

Stamford Suites

4 out of 5
720 Bedford St, Stamford, CT
Free Cancellation
Reserve now, pay when you stay
18.29 mi from city center
$132 nightly
The price is $152 total per night
$152 total
Oct 5 - Oct 6
Total with taxes and fees
At Stamford Suites, guests have access to free WiFi in public areas, express check-in, and express check-out. There's free parking if you drive. Multilingual staff at the front desk are standing by 24/7 to help with dry cleaning/laundry, luggage storage, and concierge services. Additional amenities include free newspapers, laundry facilities, and a vending machine.
Breakfast included
Kitchen
Brand New Private Share Room

Brand New Private Share Room

3 out of 5
12 Engle St, Englewood, NJ
19.49 mi from city center
Guests of Brand New Private Share Room have access to free WiFi in public areas.
Kitchen
Free WiFi
Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC

Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC

19.79 mi from city center
This vacation home is a smoke-free vacation home.
Kitchen
Free WiFi
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Ossining Large Group Rentals

How to Book Vacation Rentals in Ossining



🏠 What is the best price for Ossining vacation rentals?

Ossining vacation rentals range in price, starting at $152 per night.


🏠 What types of vacation rentals in Ossining can I rent?

Orbitz offers a wide range of Ossining rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Ossining condo rentals.


🏠 Is it free to cancel my Ossining vacation rental with Orbitz?

Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.


🏠 How do I find the best deals to rent a Ossining vacation rental with Orbitz?

There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Ossining. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.


🏠 How can I cancel my vacation rental booking through Orbitz?

Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.


🏠 What are the advantages of booking a vacation rental in Ossining?

Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Ossining apartments and enjoy an extended stay.


🏠 Why should I book my vacation rental with Orbitz in Ossining?

Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Ossining package deals will get you even more savings.

More to Explore

More to Explore