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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Ossining holiday rentals

Villa | 5 bedrooms

Holiday Home in Ossining

NEW 45 Wolden Rd Ossining NY 10562
2.0 star property
The price is ฿9,977
฿26,619 total
includes taxes & fees
15 Mar - 16 Mar
NEW 45 Wolden Rd Ossining NY 10562
Apartment (1 Bedroom) | Interior

Apartment in Greenwich

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.0 star property
The price is ฿4,568
฿11,701 total
includes taxes & fees
5 Mar - 6 Mar
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
Living area

Apartment in White Plains

Luxury 3BR Home Game Room Free Parking
2.0 star property
The price is ฿3,699
฿8,863 total
includes taxes & fees
2 Mar - 3 Mar
Luxury 3BR Home Game Room Free Parking
Private kitchen

Apartment in Bryn Mawr

Luxury 1BR located in Prime Yonkers Area
2.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"Everything was clean, good communication.. I would like to come back again for sure "
United States
Genesis
The price is ฿4,632
฿9,814 total
includes taxes & fees
28 Feb - 1 Mar
Luxury 1BR located in Prime Yonkers Area
Luxury House | Living area

Apartment in Southeast Yonkers

Spacious 3BR Luxe Escape near NYC
2.0 star property
8.0 out of 10, Very good, (2 reviews)
"Room was cold. No parking lot for vehicle. Only off-street parking was available "
United States
david
The price is ฿12,404
฿16,955 total
includes taxes & fees
28 Feb - 1 Mar
Spacious 3BR Luxe Escape near NYC
Private kitchen

Apartment in White Plains

Elegant Hideaway with Free Parking
2.0 star property
The price is ฿4,632
฿9,930 total
includes taxes & fees
28 Feb - 1 Mar
Elegant Hideaway with Free Parking
Living area

Apartment in Bryn Mawr

Luxe 1BR Oasis - Prime NY Stay
2.0 star property
The price is ฿4,661
฿9,844 total
includes taxes & fees
28 Feb - 1 Mar
Luxe 1BR Oasis - Prime NY Stay
Living area

Apartment in Bryn Mawr

Luxury 3BR Family Home Game Room Parking
2.0 star property
The price is ฿10,844
฿16,762 total
includes taxes & fees
6 Mar - 7 Mar
Luxury 3BR Family Home Game Room Parking
Private kitchen

Holiday Home in Southeast Yonkers

3BR Prime Luxury near NYC w Arcade Room
2.0 star property
8.0 out of 10, Very good, (1 review)
"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 traveller
The price is ฿12,404
฿17,887 total
includes taxes & fees
28 Feb - 1 Mar
3BR Prime Luxury near NYC w Arcade Room
Luxury Apartment | Living area

Apartment in Southeast Yonkers

NY Luxury Apt Free Parking in PRIME Area
3.0 star property
5.0 out of 10, (4 reviews)
"Everything about this place is amazing. Great location, very safe, cozy, clean. Will be back soon!"
United States
Paola
The price is ฿3,076
฿6,518 total
includes taxes & fees
28 Feb - 1 Mar
NY Luxury Apt Free Parking in PRIME Area
Living area

Apartment in Bryn Mawr

Uscale 2BR Escape in the Heart of NYC
2.0 star property
8.0 out of 10, Very good, (1 review)
"The house was very clean and the areas was quiet too. We had a nice spot to park the car. The staff was calling and checking on me if I didn’t have any issues with the check in. They were available all the time. The only thing we will need next time if possible is the washer and dryer and extra towels because we were 5 and only got 3 towels. But overall we enjoyed the stays."
United States
Adj Fatou
The price is ฿7,768
฿13,631 total
includes taxes & fees
28 Feb - 1 Mar
Uscale 2BR Escape in the Heart of NYC
Living area

Holiday Home in Bryn Mawr

Luxury 3 BR Near NYC with Easy Parking
2.0 star property
The price is ฿12,498
฿17,991 total
includes taxes & fees
28 Feb - 1 Mar
Luxury 3 BR Near NYC with Easy Parking
Dining

Apartment in White Plains

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
The price is ฿6,184
฿11,517 total
includes taxes & fees
1 Mar - 2 Mar
Prime Luxe 3-BR NYC - Free Parking
Living area

Villa in White Plains

Luxury NYC Home Game Room Free Parking
4.0 star property
The price is ฿17,090
฿24,177 total
includes taxes & fees
28 Feb - 1 Mar
Luxury NYC Home Game Room Free Parking
Exterior

Aparthotel in Downtown Stamford

Stamford Suites
4.0 star property
6.4 out of 10, (100 reviews)
"Nice clean rooms the bedding was comfortable, it smelled good walking in, I will be staying in this hotel in the next time I'm in Stamford."
United States
Fatima
The price is ฿4,327
฿4,977 total
includes taxes & fees
1 Mar - 2 Mar
Stamford Suites
Free WiFi

Apartment in Bryn Mawr

Two Wash
2.0 star property
The price is ฿11,155
฿17,110 total
includes taxes & fees
28 Feb - 1 Mar
Two Wash
House | 7 bedrooms

Holiday Home in Cornwall

NEW 5 Trinity Pl Cornwall NY 12518
2.0 star property
The price is ฿16,847
฿37,480 total
includes taxes & fees
5 Mar - 6 Mar
NEW 5 Trinity Pl Cornwall NY 12518
Outdoor dining

Apartment in White Plains

3BR Prime Luxury NY - Free Parking
2.0 star property
The price is ฿31,073
฿39,237 total
includes taxes & fees
11 Mar - 12 Mar
3BR Prime Luxury NY - Free Parking
Luxury House, Garden View | Dining

Apartment in Southeast Yonkers

Modern Comfort in the Heart of NYC
4.0 star property
2.0 out of 10, (1 review)
The price is ฿13,983
฿19,652 total
includes taxes & fees
28 Feb - 1 Mar
Modern Comfort in the Heart of NYC
Luxury House | Living area

Apartment in Southeast Yonkers

Spacious 3BR Luxe Escape near NYC
2.0 star property
2.0 out of 10, (1 review)
"Very inaccurate listing upon arriving host called me stating I could not stay at property due to issues on their end instead of offering a refund I was sent to a different property that was a 1 bedroom with 1 bed that was clearly not cleaned instead of the 3 bedroom 5 bed luxury house I initially booked I explained this would not work for me and my 4 other guests and got told there was no other choice and hung up on, me and my guests had no option beside to go back home very bad experience DO...
United States
Gerald
The price is ฿12,404
฿16,955 total
includes taxes & fees
28 Feb - 1 Mar
Spacious 3BR Luxe Escape near NYC
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

LIV Hotel Bronx

LIV Hotel Bronx

10/10 Excellent
"The room was nice "
Sabrina 1-night trip
Posted 2 days ago
LIV Hotel Bronx

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:

  • View our selection of featured holiday rentals in Ossining
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  • Enter your travel dates to view the best deals on holiday rentals in Ossining while they last

Look no further and take a look at our great range of rental properties in Ossining!

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.

How many holiday rentals will I find in Ossining?

With 7 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 Teatown Lake Reservation and Merchants Square 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.