Ossining Vacation Rentals

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Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 Jun - 28 Jun

Our top choices for Ossining holiday rentals

5 bedrooms

Holiday Home in Ossining

NEW 45 Wolden Rd Ossining NY 10562
2.0 star property
The price is RM2,066
RM4,298 total
includes taxes & fees
15 Mar - 16 Mar
NEW 45 Wolden Rd Ossining NY 10562
Interior

Apartment in Greenwich

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.0 star property
The price is RM579
RM1,483 total
includes taxes & fees
8 Mar - 9 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 RM784
RM1,484 total
includes taxes & fees
6 Mar - 7 Mar
Luxury 3BR Home Game Room Free Parking
Private kitchen

Apartment in White Plains

Elegant Hideaway with Free Parking
2.0 star property
The price is RM784
RM1,484 total
includes taxes & fees
6 Mar - 7 Mar
Elegant Hideaway with 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 RM1,414
RM2,169 total
includes taxes & fees
6 Mar - 7 Mar
Luxury 1BR located in Prime Yonkers Area
Living area

Villa in White Plains

Luxury NYC Home Game Room Free Parking
4.0 star property
The price is RM2,167
RM3,065 total
includes taxes & fees
6 Mar - 7 Mar
Luxury NYC Home Game Room Free Parking
Dining

Apartment in White Plains

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
The price is RM1,414
RM2,162 total
includes taxes & fees
6 Mar - 7 Mar
Prime Luxe 3-BR NYC - Free Parking
Living area

Apartment in Bryn Mawr

Luxury 3BR Family Home Game Room Parking
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Beautiful layout. Property had everything that was needed for an awesome stay."
United States
Ashley
The price is RM1,375
RM2,125 total
includes taxes & fees
6 Mar - 7 Mar
Luxury 3BR Family Home Game Room Parking
Living area

Holiday Home in Bryn Mawr

Luxury 3 BR Near NYC with Easy Parking
2.0 star property
The price is RM1,585
RM2,281 total
includes taxes & fees
6 Mar - 7 Mar
Luxury 3 BR Near NYC with Easy Parking
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 RM1,375
RM2,165 total
includes taxes & fees
6 Mar - 7 Mar
Uscale 2BR Escape in the Heart of NYC
Living area

Apartment in Bryn Mawr

Luxe 1BR Oasis - Prime NY Stay
2.0 star property
The price is RM1,375
RM2,125 total
includes taxes & fees
6 Mar - 7 Mar
Luxe 1BR Oasis - Prime NY Stay
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 RM1,773
RM2,373 total
includes taxes & fees
6 Mar - 7 Mar
Spacious 3BR Luxe Escape near NYC
Exterior

Aparthotel in Downtown Stamford

Stamford Suites
4.0 star property
6.4 out of 10, (101 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 RM485
RM557 total
includes taxes & fees
8 Mar - 9 Mar
Stamford Suites
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 RM429
RM870 total
includes taxes & fees
8 Mar - 9 Mar
NY Luxury Apt Free Parking in PRIME Area
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 RM2,360
RM3,148 total
includes taxes & fees
6 Mar - 7 Mar
3BR Prime Luxury near NYC w Arcade Room
Free WiFi

Apartment in Bryn Mawr

Two Wash
2.0 star property
The price is RM3,743
RM4,774 total
includes taxes & fees
8 Mar - 9 Mar
Two Wash
7 bedrooms

Holiday Home in Cornwall

NEW 5 Trinity Pl Cornwall NY 12518
2.0 star property
The price is RM1,916
RM4,482 total
includes taxes & fees
16 Mar - 17 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 RM3,940
RM4,975 total
includes taxes & fees
6 Mar - 7 Mar
3BR Prime Luxury NY - Free Parking
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 RM1,773
RM2,491 total
includes taxes & fees
6 Mar - 7 Mar
Modern Comfort in the Heart of NYC
Dining

Villa in White Plains

Luxury NYC Home with Free Parking for 12
4.0 star property
2.0 out of 10, (1 review)
"Place didn't exist. Host did not respond to requests to clarify check-in. Upon arriving, the location was not as described and an individual who answered the door informed our party this was not a rental property. Had to last minute book elsewhere."
United States
Kathleen
The price is RM1,773
RM2,680 total
includes taxes & fees
6 Mar - 7 Mar
Luxury NYC Home with Free Parking for 12
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

Ardsley Acres Hotel Westchester

Ardsley Acres Hotel Westchester

10/10 Excellent
"It was a nice stay. "
Najimu 1-night trip
Posted 1 hour ago
Ardsley Acres Hotel Westchester

Find out more about Ossining

Search for holiday rentals in Ossining on Expedia.co.uk! 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 Kitchawan Preserve 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.