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Ossining Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Ossining vacation rentals

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

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

2.0 star property
Ossining
$245 nightly
The price is $279
Dec 14 - Dec 15
Total with taxes and fees
1BR Queen near NYC | Trails, Biking & Sauna Bliss
Interior
Near NYC! | Stylish Guestroom

Near NYC! | Stylish Guestroom

2.0 star property
Ossining
$256 nightly
The price is $292
Dec 14 - Dec 15
Total with taxes and fees
Near NYC! | Stylish Guestroom
Lobby
Stamford Suites

Stamford Suites

4.0 star property
Downtown Stamford
6.2 out of 10, (78)
"It was great"
United States
Natalie
$120 nightly
The price is $138
Dec 28 - Dec 29
Total with taxes and fees
Stamford Suites
Luxury House | Private kitchen
Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC

2.0 star property
Southeast Yonkers
$423 nightly
The price is $474
Jan 5 - Jan 6, 2026
Total with taxes and fees
Spacious 3BR Luxe Escape near NYC
Terrace/patio
3BR Prime Luxury near NYC w Arcade Room

3BR Prime Luxury near NYC w Arcade Room

2.0 star property
Southeast Yonkers
8.0 out of 10, Very Good, (1)
"We thought we rented the entire property, but was half of it. expect a lot of stairs. No bath tubs but two showers. some door knobs and locks need maintenance, but overall nice clean rooms."
United States
Anonymous traveler
$687 nightly
The price is $769
Dec 11 - Dec 12
Total with taxes and fees
3BR Prime Luxury near NYC w Arcade Room
Luxury House, Garden View | Private kitchen | Full-size fridge, microwave, oven, stovetop
Modern Comfort in the Heart of NYC

Modern Comfort in the Heart of NYC

4.0 star property
Southeast Yonkers
$538 nightly
The price is $602
Dec 11 - Dec 12
Total with taxes and fees
Modern Comfort in the Heart of NYC
Reception
Global Luxury Suites White Plains

Global Luxury Suites White Plains

3.5 star property
White Plains
6.8 out of 10, (33)
"Being in an apartment building for an actual stay instead of a house was a first for myself and the family but overall a good stay."
United States
Ramon
Global Luxury Suites White Plains
Lounge
Luxury Apartments by Hyatus at The Asher

Luxury Apartments by Hyatus at The Asher

4.5 star property
Downtown Stamford
10.0 out of 10, Exceptional, (19)
"Clean and had everything you need for longer stay Comfortable "
United States
christine
Luxury Apartments by Hyatus at The Asher
Property grounds
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.

Greenwich
9.6 out of 10, Exceptional, (23)
"The property was beautiful and clean, very comfortable with a nice view of the lake! Our hosts were helpful and attentive without being intrusive in any way. Our stay was peaceful and restful, just perfect. "
United States
Victoria R.
$228 nightly
The price is $258
Dec 15 - Dec 16
Total with taxes and fees
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
House | Living area
Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking

3.0 star property
Southeast Yonkers
7.2 out of 10, Good, (5)
"This was an excellent House My birthday weekend was amazing I totally would book again"
United States
Keisheena
Modern Luxury Home w GameRoom & Parking
2 bedrooms, in-room safe, WiFi
Elegant 2BR Modern Oasis Brand-New Build, Luxe Touches & Lightning-Fast WiFi, AC

Elegant 2BR Modern Oasis Brand-New Build, Luxe Touches & Lightning-Fast WiFi, AC

Bronx
9.0 out of 10, Wonderful, (8)
"We had a wonderful time. The apartment was exactly as described in the posting. Every room was super clean, bright, and welcoming. We were very comfortable. Eche was very helpful. We appreciated how quickly he responded to our questions. He checked in with us and made sure we had everything we needed. Many nice extra touches made us feel at home. We plan to stay here next time we are in town!"
United States
Karen C.
Elegant 2BR Modern Oasis Brand-New Build, Luxe Touches & Lightning-Fast WiFi, AC
Smart TV
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

Bronx
9.8 out of 10, Exceptional, (14)
"Excellent property close to Fordham, very clean and nice amenities! Hope to stay here on our next visit to see our daughter at Fordham."
United States
Amy B.
Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery
9.8 out of 10, Exceptional, (129)
"It has an incredible mountain and water view. "
United States
MIHYUN
$271 nightly
The price is $307
Dec 11 - Dec 12
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Smart TV
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

Scarsdale
9.2 out of 10, Wonderful, (5)
"The owner was very responsive and kind. The apartment was very clean and well updated. We are older adults and the access to the basement apartment was a bit of a challenge but the owner did graciously help with our luggage. The family does clearly disclose that they live above the unit and sounds of children may be heard. Between the sounds of the family above and the fact it’s a basement, not a “Loft”, with all the plumbing just above your head - it was not for us. "
United States
Annette D.
$278 nightly
The price is $318
Jan 4 - Jan 5, 2026
Total with taxes and fees
Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic
Living area
Luxury NY Home close to NYC

Luxury NY Home close to NYC

2.0 star property
Southeast Yonkers
2.0 out of 10, (1)
"This way by far the worst experience of any place I have every stayed at. The place is not anywhere near what the pictures or descriptions conveyed and worse the owner and host are immoral and distrustful. Heres a brief description of the physical issues from least worst to worst. 1) No Laundry facilities. It was listed there was and I had 4 people so you can imagine the hassle with going to a laundromat. 2) Temperature. The heat was turned WAY up and there was no way to turn it down. ...
United States
MARC S
Luxury NY Home close to NYC
In-room dining
Luxury Living in the Heart of NY

Luxury Living in the Heart of NY

4.0 star property
Southeast Yonkers
2.0 out of 10, (1)
"The photos of the unit were beautiful however the wear and tear on the actual property did not compare. The bathroom sink constantly leaked and because the floors were not even they stayed wet. The nightstands were broken the refrigerator would not open all the way. I also was not notified until the day of check in that the unit was on the 3rd floor and there was 2 flights of stairs just to get to the entrance to the unit."
United States
Ebony
Luxury Living in the Heart of NY
Fridge, microwave, oven, stovetop
Marvelous 5-bedroom house with AC in Yonkers

Marvelous 5-bedroom house with AC in Yonkers

2.0 star property
Bryn Mawr
2.0 out of 10, (1)
"Cancelled my stay at check out time while I was at the NY airport— said there was a “power outage”. “Upgraded” me to a luxury property that turned out to be a dirty 3rd floor walk up. When I asked for a refund, they lied to VRBO and said I never showed up. I had to prove to VRBO with texts and phone records that they cancelled me. I suspected a bait and switch. Also, VRBO had to start an investigation because the phone number from the owner was an unknown number—my information had been...
United States
Amy L.
Marvelous 5-bedroom house with AC in Yonkers
Outdoor dining
Eaglefest time! Plus stunning winter views of Croton River Gorge, a birder haven

Eaglefest time! Plus stunning winter views of Croton River Gorge, a birder haven

Croton-on-Hudson
9.6 out of 10, Exceptional, (15)
"We enjoyed our overnight stay at this quaint nicely appointed carriage house."
United States
Cathleen C.
Eaglefest time! Plus stunning winter views of Croton River Gorge, a birder haven
Terrace/patio
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Southeast Yonkers
8.2 out of 10, Very Good, (18)
"Great place great location"
United States
Daquan H.
$115 nightly
The price is $135
Dec 14 - Dec 15
Total with taxes and fees
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Fridge, microwave, oven, stovetop
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

Northeast Yonkers
8.6 out of 10, Excellent, (45)
"Very clean property in a quiet neighborhood. Convenient shopping only minutes away (including a Costco). We would definitely stay there again."
United States
Dan F.
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
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.
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Top Ossining Hotel Reviews

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

10/10 Excellent
"Cute "
Bill Stephania C 1-night trip
Posted 1 day ago
DoubleTree by Hilton Hotel Nanuet

Find out more about Ossining

Everything you need to know about Ossining vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Ossining vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Ossining vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Ossining vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Ossining. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Ossining in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $135 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Ossining rentals

At Expedia, we put the best Ossining vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Ossining rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Ossining vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Ossining. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Ossining?

Yes, there are vacation rentals close to well known attractions in Ossining, or you can go with a more remote option if you're looking for a relaxing stay. Ossining is known for its restaurants and parks. Make sure you have time to check out the golf courses and university setting during your trip.

What's the top vacation rental that Ossining has to offer?

3BR Prime Luxury near NYC w Arcade Room: You might want to consider this vacation home rental near Ossining, which is near the airport and offers free WiFi to help you feel perfectly comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals will I find in Ossining?

With 7 Expedia vacation rentals, you're sure to find just the right place for your Ossining stay.

What’s there to see and do in Ossining?

Cultural attractions include Sing Sing Prison Museum and Ossining Historical Society, whereas Teatown Lake Reservation and Kitchawan Preserve are a couple of picturesque spots to enjoy the outdoors. Sing Sing Correctional Facility and Thomas J. Watson Research Center are other places to visit while you're in town.

What’s a vacation rental in Ossining like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Ossining. Vacation rentals feature extras like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from public hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for families.