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Ossining Vacation Rentals

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Check prices for these dates

Tonight
Aug 20 - Aug 21
Tomorrow
Aug 21 - Aug 22
This weekend
Aug 22 - Aug 24
Next weekend
Aug 29 - Aug 31

Vacation Rentals in Ossining

Summer Castle: Pool, Game Room, BBQ - Pet Friendly
Outdoor banquet area

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

8.6 out of 10, Excellent, (4)
"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. "
$1,126 nightly
The price is $1,160
Aug 24 - Aug 25
Total includes taxes and fees
Summer Castle: Pool, Game Room, BBQ - Pet Friendly
Stamford Suites
Lobby

Stamford Suites

4.0 star property
5.6 out of 10, (49)
"Excellent sleep"
$130 nightly
The price is $149
Sep 1 - Sep 2
Total includes taxes and fees
Stamford Suites
3BR Prime Luxury near NYC w Arcade Room
Terrace/patio

3BR Prime Luxury near NYC w Arcade Room

2.0 star property
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."
$687 nightly
The price is $769
Aug 21 - Aug 22
Total includes taxes and fees
3BR Prime Luxury near NYC w Arcade Room
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Property grounds

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

9.0 out of 10, Wonderful, (7)
"Perfect place to rest. Excellent service! "
$285 nightly
The price is $323
Aug 21 - Aug 22
Total includes taxes and fees
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (119)
"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…."
$271 nightly
The price is $307
Sep 8 - Sep 9
Total includes taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Global Luxury Suites White Plains
Reception

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
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
Fridge, microwave, oven, stovetop

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

9.0 out of 10, Wonderful, (36)
"Short trip. great place to stay . Very cozy . Family loved it "
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
Stunning 2BR next to Bronx Zoo
Fridge, microwave, oven, stovetop

Stunning 2BR next to Bronx Zoo

2.0 out of 10, (2)
"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...
$364 nightly
The price is $398
Aug 21 - Aug 22
Total includes taxes and fees
Stunning 2BR next to Bronx Zoo
Modern Luxury Home w GameRoom & Parking
House | Living area

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...
$643 nightly
The price is $708
Aug 21 - Aug 22
Total includes taxes and fees
Modern Luxury Home w GameRoom & Parking
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Terrace/patio

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

8.0 out of 10, Very Good, (16)
"Great place great location"
$115 nightly
The price is $135
Aug 21 - Aug 22
Total includes taxes and fees
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Luxury Living in the Heart of NY
In-room dining

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
Cozy Apartment-Just minutes from New York City
Smart TV

Cozy Apartment-Just minutes from New York City

9.4 out of 10, Exceptional, (6)
"Nice place to stay "
Cozy Apartment-Just minutes from New York City
Luxury 5BR 2BA Spacious Home NYC Free Parking + Office
Living area

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

Luxury 5BR 2BA Spacious Home NYC Free Parking + Office
Luxury Apartments by Hyatus at The Asher
Lounge

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

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

10.0 out of 10, Exceptional, (1)
"I chose this apartment for its location primarily and it was a hit. Since we were traveling and staying for two weeks with a toddler and a new baby I was looking for it to also have an outdoor space, and it was wonderful as seen in the pictures. For personal reasons I had to change my dates a few days before my booking was coming up, the hosts had no problem to accommodate my needs. During our stay, we even had the opportunity to meet the neighbor next door and visit her garden. The neighborhood...
$282 nightly
The price is $323
Sep 8 - Sep 9
Total includes taxes and fees
Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (87)
"It was very nice "
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC
Smart TV

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

9.8 out of 10, Exceptional, (6)
"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
Castle in The Sky ! Beautifully Renovated Victorian one Block from Main St.
Exterior

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.
Piermont Oasis
Property grounds

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."
$197 nightly
The price is $219
Sep 9 - Sep 10
Total includes taxes and fees
Piermont Oasis
Romantic retreat with stunning views of Croton River Gorge, a birder haven
Outdoor dining

Romantic retreat with stunning views of Croton River Gorge, a birder haven

9.8 out of 10, Exceptional, (7)
"I hesitate to sound too over the top in my praise of the Carriage House in Croton, but it’s difficult not to. The space is so comfortable, cozy, and filled with beautiful Mexican art pieces every where you look. Nothing has been forgotten by the hosts, who are charming and gracious, while allowing guests absolute privacy.The Carriage House is surrounded by natural beauty everywhere you look. From the Croton River below, to the wild turkeys in the morning and evening, and the omnipresent sound...
Romantic retreat with stunning views of Croton River Gorge, a birder haven
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

Sonesta Simply Suites Nanuet

Sonesta Simply Suites Nanuet

10/10 Excellent
"Quiet"
willie 2-night trip
Posted 1 day ago
Sonesta Simply Suites Nanuet

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 Teatown Lake Reservation 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.