Ossining Vacation Rentals from ￥20,066: Search Short-Term Rentals

Q: 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. Another good choice for your trip to Ossining is Castle Retreat w/ Pool, BBQ, Game Room & Pets OK! .

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Vacation Rentals in Ossining

"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. "

"Excellent sleep"

￥22,413 total

includes taxes & fees

Oct 20 - Oct 21

"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."

￥114,461 total

includes taxes & fees

Sep 26 - Sep 27

"Perfect place to rest. Excellent service! "

￥30,059 total

includes taxes & fees

Sep 29 - Sep 30

"Everything was very clean and cozy.We have enjoyed our stay there. "

"It has an incredible mountain and water view. "

￥45,793 total

includes taxes & fees

Sep 30 - Oct 1

"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...

"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."

32-inch flat-screen TV with cable channels, TV

"Very clean, comfortable, and quiet property. Although advertised one car parking, actually can park 2, which is good since limited street parking in a crowded neighborhood. Highly recommended if you're staying in the NYC area."

"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. "

￥47,610 total

includes taxes & fees

Oct 7 - Oct 8

"We loved our stay at the Carriage House. Patrick and Kathryn were wonderful hosts. They provided information in a timely manner, and were quick to respond to any questions. Our accommodations were clean, comfortable and well appointed, and Patrick and Kathryn included truly thoughtful touches. The location was perfect for exploring Croton-on-Hudson and the Hudson Valley. We'd love to come back!"

"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."

"This place truly felt like a home away from home. Everything was spotless, comfortable, and well cared for. The location made it easy to access everything we needed, whether dining, shopping, or exploring the area. I would definitely return!"

"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."

"Great place great location"

￥20,066 total

includes taxes & fees

Sep 29 - Sep 30

"We only stayed a couple days, but the location is quaint and apartment newly refurnished. The owner was very helpful and great to work with. Highly recommend!"

"If I could give this place zero stars, I would. Upon arrival, I received no check-in information, which immediately set the tone for a frustrating experience. When I got to the property, the front door was already open, raising serious concerns about security. Inside, the floors were dirty, the beds were unmade, and the trash from the previous guests had not been removed. There were bugs throughout the space, and the front door handle was broken, making the property feel unsafe and poorly...

1 bedroom, iron/ironing board, free WiFi, bed sheets

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Top Ossining Hotel Reviews

Hyatt Place New York/Yonkers

10/10 Excellent

"Perfect location and the staff was very helpful and friendly. "

Find out more about Ossining

Search for holiday rentals in Ossining on Expedia! You can easily find your home rentals, villas, holiday apartments in Ossining using one of the methods below:

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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. Another good choice for your trip to Ossining is Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!.

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.

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Ossining Vacation Rentals

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Vacation Rentals in Ossining

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

Stamford Suites

3BR Prime Luxury near NYC w Arcade Room

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

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

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Modern Luxury Home w GameRoom & Parking

Global Luxury Suites White Plains

Brand New Private Share Room

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

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

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

Luxury Living in the Heart of NY

Luxury Apartments by Hyatus at The Asher

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

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

Ideal Location 1block to Main St. Restaurants , Bars,Hudson River, Bus/ Train

Luxury 10BR Escape w/ Pool, Hot Tub & Game Lounge

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

Elegant Hideaway • Free Parking

Top Ossining Hotel Reviews

Hyatt Place New York/Yonkers

Amsterdam Hotel

Baymont by Wyndham White Plains - Elmsford

Armoni Inn & Suites

Hotel Nyack, a JdV by Hyatt Hotel

Ardsley Acres Hotel Westchester

Royal Regency Hotel

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

Sonesta Simply Suites Nanuet

Find out more about Ossining

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