Ossining Holiday Rentals: Short-Term Accommodations for Rent

Q: What are some of the best holiday rentals that Ossining has to offer?

Summer Castle: Pool, Game Room, BBQ - Pet Friendly : This highly rated holiday home rental in Ossining is located near skiing, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

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Holiday Rentals in Ossining

Our top choices for Ossining holiday rentals

"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"

HK$1,082 total

includes taxes & fees

3 Sept - 4 Sept

"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."

HK$5,997 total

includes taxes & fees

3 Sept - 4 Sept

"Perfect place to rest. Excellent service! "

HK$2,282 total

includes taxes & fees

3 Sept - 4 Sept

"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...

HK$3,288 total

includes taxes & fees

3 Sept - 4 Sept

"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."

"It has an incredible mountain and water view. "

HK$2,399 total

includes taxes & fees

7 Sept - 8 Sept

"Short trip. great place to stay . Very cozy . Family loved it "

"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...

HK$4,068 total

includes taxes & fees

3 Sept - 4 Sept

"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...

HK$2,514 total

includes taxes & fees

7 Sept - 8 Sept

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

"Great place great location"

HK$1,051 total

includes taxes & fees

11 Sept - 12 Sept

"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."

"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."

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

"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...

"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."

HK$1,745 total

includes taxes & fees

8 Sept - 9 Sept

"Patrick and Katherine are excellent hosts with an incredible property in an amazing location. We had such an incredible time. The carriage house is so comfortable and welcoming. I absolutely loved just sitting on the balcony enjoying the beautiful view, birds, and my coffee. This was my first time using Vrbo, (glad to have found an alternative to another site I no longer support). Wow, I have been missing out!! The stocked fridge was such a lovely surprise. Everything was just fantastic. Our...

"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!"

"cleanliness. quiet. "

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Top Ossining Hotel Reviews

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 holiday rental in Ossining?

Yes, there are holiday rentals close to the most popular sights in Ossining, or you can select a more secluded 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 are some of the best holiday rentals that Ossining has to offer?

Summer Castle: Pool, Game Room, BBQ - Pet Friendly: This highly rated holiday home rental in Ossining is located near skiing, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals will I find in Ossining?

With 6 Expedia holiday rentals, you're guaranteed 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 holiday rental in Ossining like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Ossining. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for a family getaway.

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Ossining Holiday Rentals

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Holiday Rentals in Ossining

Our top choices for Ossining holiday rentals

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.

Stunning 2BR next to Bronx Zoo

Global Luxury Suites White Plains

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

Modern Luxury Home w GameRoom & Parking

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

Brand New Private Share Room

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

Luxury Living in the Heart of NY

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

Elegant Hideaway • Free Parking

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

Piermont Oasis

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

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

Luxury Apartments by Hyatus at The Asher

Top Ossining Hotel Reviews

Find out more about Ossining

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Frequently asked questions