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Ossining Vacation Rentals

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Vacation Rentals in Ossining

Summer Castle: Pool, Game Room, BBQ - Pet Friendly

8.0 out of 10, Very good, (3)
"We booked the property because our family is growing too large for all of the children and grandchildren to spend the holidays together. The “holiday house” as our 4 year old coined it was the perfect place to spend Christmas and Hanukkah. Large yet cozy and very well appointed. All of our communication with proprietors was prompt and helpful, and they had the driveway salted and plowed within hours of the (very picturesque) snowfall the day before Christmas. I would happily book here again. "
The price is CA $1,129
CA $1,900 total
includes taxes & fees
Aug 25 - Aug 26
Summer Castle: Pool, Game Room, BBQ - Pet Friendly

Stamford Suites

4.0 star property
5.6 out of 10, (48)
"It was great relaxing stay"
The price is CA $191
CA $220 total
includes taxes & fees
Aug 11 - Aug 12
Stamford Suites

3BR Prime Luxury near NYC w Arcade Room

2.0 star property
The price is CA $826
CA $1,060 total
includes taxes & fees
Aug 5 - Aug 6
3BR Prime Luxury near NYC w Arcade Room

Global Luxury Suites White Plains

3.5 star property
6.8 out of 10, (31)
"This place a marvelous!! Very nice and clean!! The scenery of nature that I experienced when waking up was very refreshing!!"
Global Luxury Suites White Plains

Stunning 2BR next to Bronx Zoo

2.0 out of 10, (1)
"This property was at most the horrible experience. Property is not at all where it states on the website. When we arrived the ceiling was falling due to an old leakage and when I communicated with someone in charge of property, they said maintenance will come. We stood for a week and they came at the second to last day of our stay. It was cold every morning and the windows were patched with garbage bags. Everything was prone to disconnect from walls such as everything in bathroom. In addition to...
The price is CA $219
CA $548 total
includes taxes & fees
Aug 5 - Aug 6
Stunning 2BR next to Bronx Zoo

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (118)
"Nice view on the top of the mountain….I admired the river with the bridge and the surroundings until late in the night. The accommodation was excellent, we had everything we needed.… we are thinking of coming back sometime…."
The price is CA $280
CA $443 total
includes taxes & fees
Aug 25 - Aug 26
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Cozy Apartment-Just minutes from New York City

9.2 out of 10, Wonderful, (5)
"Nice place to stay "
Cozy Apartment-Just minutes from New York City

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (85)
"We loved our stay. It was great for a family Thanksgiving"
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Luxury 5BR 2BA Spacious Home NYC Free Parking + Office

Luxury 5BR 2BA Spacious Home NYC Free Parking + Office

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

10.0 out of 10, Exceptional, (5)
"This was a great experience. Eche was an incredible communicator and seized quickly on any request we had and got it sorted almost before the phone call ended. The apartment is clean and lovely with a seriously undersold view of the reservoir, which sparkled in the morning sunlight through the wall-to-wall windows. WE WILL BE RETURNING TO THIS PROPERTY. And We still can’t believe we were in the middle of the Bronx. Thanks, Eche!"
Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC

Luxury Living in the Heart of NY

4.0 star property
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."
Luxury Living in the Heart of NY

Modern Luxury Home w GameRoom & Parking

3.0 star property
7.0 out of 10, Good, (4)
"Put down a deposit with the understanding that the deposit would be back in my account within 24 hours. Messaged them several times and I have not gotten any response nor have I gotten my money back and it has been days now with no response. Apartment was filthy, beds were used and not cleaned, bunch of appliances didn’t work, found a towel with stains potentially from bodily fluids.DO NOT BOOK WITH THEM THEY ARE SCAMMERS. Charged a cleaning fee on top of this for an apartment that wasn’t even...
The price is CA $769
CA $997 total
includes taxes & fees
Aug 5 - Aug 6
Modern Luxury Home w GameRoom & Parking

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

9.0 out of 10, Wonderful, (36)
"Perfect place and plenty of parking. "
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

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

8.0 out of 10, Very good, (16)
"Great place great location"
The price is CA $130
CA $186 total
includes taxes & fees
Aug 9 - Aug 10
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Cozy private room

2.0 star property
6.2 out of 10, (14)
"Please give me my money back. I no longer use the private room you rented. I went there and I couldn't get in. The code you gave me didn't work. I waited until 4 o'clock and I couldn't get in "
Cozy private room

Luxury Apartments by Hyatus at The Asher

4.5 star property
10.0 out of 10, Exceptional, (16)
"The covered parking was really helpful on a cold day."
Luxury Apartments by Hyatus at The Asher

Piermont Oasis

10.0 out of 10, Exceptional, (2)
"Carolyn was so amazing with her directions on how to park and check in. The apartment had everything as advertised. The ambiance was very private and peaceful. Walking distance to the town and pier. I would definitely stay again."
The price is CA $199
CA $330 total
includes taxes & fees
Sep 2 - Sep 3
Piermont Oasis

Private lake escape

Private lake escape

Castle in The Sky ! Beautifully Renovated Victorian one Block from Main St.

9.0 out of 10, Wonderful, (6)
"Large comfortable home in great location with multiple views of the Hudson. Our family had a pleasant stay and would definitely return to Castle in the Sky."
Castle in The Sky ! Beautifully Renovated Victorian one Block from Main St.

Luxury NY Home 3BR with Easy Parking

3.0 star property
3.0 out of 10, (4)
"I was fooled by the pictures. Upon check-in, they require to zelle cleaing fee. When I finally got inside, I found absolutely nothing lux about this property, no comfort and hospitality. The broken floor welcome me, all 4 beds are broken, only 2 TVs, moldy restroom, zero confort. They left 4 towels for 6 people for 6 nights. I had to request more towels. I had to scoop water fromthe shower to flush in the toilet because water would not drain. Half roll toilet paper was left. If you take...
The price is CA $520
CA $718 total
includes taxes & fees
Aug 7 - Aug 8
Luxury NY Home 3BR with Easy Parking
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

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 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 6 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 Depot Square and Ossining Dog Park 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.