Ossining Vacation Rentals

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Check prices for these dates

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

Our top choices for Ossining vacation rentals

Villa | 5 bedrooms

Vacation Home in Ossining

NEW 45 Wolden Rd Ossining NY 10562
2.0 star property
The price is NT$10,057
NT$26,831 total
includes taxes & fees
Mar 19 - Mar 20
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 NT$4,604
NT$11,794 total
includes taxes & fees
Feb 28 - Mar 1
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 NT$3,727
NT$8,930 total
includes taxes & fees
Mar 2 - Mar 3
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 NT$4,667
NT$9,888 total
includes taxes & fees
Feb 27 - Feb 28
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 NT$12,497
NT$17,081 total
includes taxes & fees
Feb 27 - Feb 28
Spacious 3BR Luxe Escape near NYC
Private kitchen

Apartment in White Plains

Elegant Hideaway with Free Parking
2.0 star property
The price is NT$4,667
NT$10,004 total
includes taxes & fees
Feb 27 - Feb 28
Elegant Hideaway with Free Parking
Living area

Apartment in Bryn Mawr

Luxe 1BR Oasis - Prime NY Stay
2.0 star property
The price is NT$4,698
NT$9,923 total
includes taxes & fees
Feb 27 - Feb 28
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 NT$7,799
NT$13,391 total
includes taxes & fees
Feb 27 - Feb 28
Luxury 3BR Family Home Game Room Parking
Private kitchen

Vacation 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 traveler
The price is NT$12,497
NT$18,021 total
includes taxes & fees
Feb 27 - Feb 28
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 NT$3,101
NT$6,570 total
includes taxes & fees
Feb 27 - Feb 28
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 NT$7,830
NT$13,740 total
includes taxes & fees
Feb 27 - Feb 28
Uscale 2BR Escape in the Heart of NYC
Living area

Vacation Home in Bryn Mawr

Luxury 3 BR Near NYC with Easy Parking
2.0 star property
The price is NT$12,598
NT$18,134 total
includes taxes & fees
Feb 27 - Feb 28
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 NT$6,233
NT$11,608 total
includes taxes & fees
Mar 1 - Mar 2
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 NT$17,226
NT$24,369 total
includes taxes & fees
Feb 27 - Feb 28
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 NT$4,378
NT$5,035 total
includes taxes & fees
Mar 1 - Mar 2
Stamford Suites
Free WiFi

Apartment in Bryn Mawr

Two Wash
2.0 star property
The price is NT$11,244
NT$17,246 total
includes taxes & fees
Feb 27 - Feb 28
Two Wash
House | 7 bedrooms

Vacation Home in Cornwall

NEW 5 Trinity Pl Cornwall NY 12518
2.0 star property
The price is NT$15,930
NT$36,485 total
includes taxes & fees
Mar 2 - Mar 3
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 NT$31,320
NT$39,549 total
includes taxes & fees
Feb 27 - Feb 28
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 NT$14,094
NT$19,808 total
includes taxes & fees
Mar 12 - Mar 13
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 NT$12,549
NT$17,153 total
includes taxes & fees
Feb 27 - Feb 28
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

Royal Hotel Bronx

Royal Hotel Bronx

10/10 Excellent
"Good hotel need mini refrigerator "
Randy 2-night trip
Posted 2 days ago
Royal 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:

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

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.

How many vacation rentals will I find in Ossining?

With 7 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 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 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.