A wooden boardwalk winding through a forest with autumn foliage.

Ossining Vacation Rentals

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sep - 13 Sep
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Ossining vacation rentals

House | 5 bedrooms

Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is AED 3,668
AED 5,857 total
includes taxes & fees
15 Jul - 16 Jul
Summer Pool Oasis Custom Bar Arcade Pool Table
House | Living area

Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking
3.5 star property
Southeast Yonkers
5.6 out of 10, (8 reviews)
"Property bedding was dirty, carpet dirty, sofas were dirty. Not was listed in the pictures. Asked me for $900 deposit through Zelle. No respond. Expedia needs to investigate this company for false advertising. "
United States
Liliana
The price is AED 2,387
AED 3,218 total
includes taxes & fees
15 Jul - 16 Jul
Modern Luxury Home w GameRoom & Parking
Luxury House | Living area

Two Wash

Two Wash
2.0 star property
Bryn Mawr
The price is AED 2,020
AED 2,807 total
includes taxes & fees
15 Jul - 16 Jul
Two Wash
House | 7 bedrooms

West Point Summer Pool Jacuzzi Events Pets OK

West Point Summer Pool Jacuzzi Events Pets OK
2.0 star property
Cornwall
The price is AED 3,458
AED 6,064 total
includes taxes & fees
15 Jul - 16 Jul
West Point Summer Pool Jacuzzi Events Pets OK
Luxury Apartment | Living area

Luxury 3 BR Near NYC with Easy Parking

Luxury 3 BR Near NYC with Easy Parking
2.0 star property
Bryn Mawr
The price is AED 1,149
AED 1,833 total
includes taxes & fees
15 Jul - 16 Jul
Luxury 3 BR Near NYC with Easy Parking
Dining

Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is AED 2,387
AED 3,206 total
includes taxes & fees
15 Jul - 16 Jul
Prime Luxe 3-BR NYC - Free Parking
Luxury Villa, Garden View | Dining

Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12
4.0 star property
White Plains
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 AED 1,286
AED 2,089 total
includes taxes & fees
15 Jul - 16 Jul
Luxury NYC Home with Free Parking for 12
Villa, Garden View | Living area

Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
4.0 out of 10, (1 review)
"After flying in with four of us from Los Angeles on a Red Eye, we had to drive around for 4-5 hours until we were able to check in at 4pm, however after hours of trying to get into the property with no answer on the contact number ,we finally were able to have the local property manager come out and say that the property overbooked and had no room for us. I spent over 2 hours on the phone getting the run around by Expedia with mixed stories of our accommodations. FINALLY with now the story is...
United States
Jorge
The price is AED 1,286
AED 2,018 total
includes taxes & fees
15 Jul - 16 Jul
Luxury NYC Home Game Room Free Parking
Luxury Villa, Patio | Living area

Luxury 5 BR Home Free Parking

Luxury 5 BR Home Free Parking
2.0 star property
Bryn Mawr
2.0 out of 10, (1 review)
The price is AED 1,653
AED 2,396 total
includes taxes & fees
26 Jul - 27 Jul
Luxury 5 BR Home Free Parking
Luxury House, Garden View | Dining

Modern Comfort in the Heart of NYC

Modern Comfort in the Heart of NYC
4.0 star property
Southeast Yonkers
3.6 out of 10, (4 reviews)
"We never got to stay because THERE WAS ANOTHER FAMILY THERE. THAT WOMEN SAID SHE WAS RENTING THE HOUSE FOR ANOTHER MONTH. "
United States
Angel
The price is AED 1,080
AED 1,755 total
includes taxes & fees
15 Jul - 16 Jul
Modern Comfort in the Heart of NYC
Apartment (1 Bedroom) | Interior

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.0 star property
Greenwich
The price is AED 904
AED 1,685 total
includes taxes & fees
15 Jul - 16 Jul
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
Luxury House | Living area

Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
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 AED 1,286
AED 1,985 total
includes taxes & fees
15 Jul - 16 Jul
Spacious 3BR Luxe Escape near NYC
Luxury Apartment | Private kitchen

Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
The price is AED 731
AED 1,383 total
includes taxes & fees
3 Aug - 4 Aug
Elegant Hideaway with Free Parking
Luxury Apartment | In-room dining

3BR Prime Luxury NY - Free Parking

3BR Prime Luxury NY - Free Parking
2.0 star property
White Plains
6.0 out of 10, (1 review)
"Check-in was confusing and poorly organized, which made the start of the stay frustrating. The room itself was fine and comfortable, but the photos on the website were misleading and didn’t match what we saw in person. Overall, an okay room but not the experience we expected."
United States
Osmond
The price is AED 3,673
AED 4,638 total
includes taxes & fees
15 Jul - 16 Jul
3BR Prime Luxury NY - Free Parking
Luxury House, Garden View | Living area

Luxury 3BR Family Home Game Room Parking

Luxury 3BR Family Home Game Room Parking
2.0 star property
Bryn Mawr
6.8 out of 10, (3 reviews)
"Beautiful layout. Property had everything that was needed for an awesome stay."
United States
Ashley
The price is AED 1,282
AED 1,981 total
includes taxes & fees
3 Aug - 4 Aug
Luxury 3BR Family Home Game Room Parking
Luxury Duplex | Living area

Uscale 2BR Escape in the Heart of NYC

Uscale 2BR Escape in the Heart of NYC
2.0 star property
Bryn Mawr
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 AED 1,084
AED 1,796 total
includes taxes & fees
15 Jul - 16 Jul
Uscale 2BR Escape in the Heart of NYC
Luxury Apartment | Living area

Luxury 1BR located in Prime Yonkers Area

Luxury 1BR located in Prime Yonkers Area
2.0 star property
Bryn Mawr
4.8 out of 10, (6 reviews)
"Everything was clean, good communication.. I would like to come back again for sure "
United States
Genesis
The price is AED 1,286
AED 1,986 total
includes taxes & fees
15 Jul - 16 Jul
Luxury 1BR located in Prime Yonkers Area
Luxury House | Living area

Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
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 AED 1,653
AED 2,396 total
includes taxes & fees
7 Aug - 8 Aug
Spacious 3BR Luxe Escape near NYC
Luxury Apartment | Living area

NY Luxury Apt Free Parking in PRIME Area

NY Luxury Apt Free Parking in PRIME Area
3.0 star property
Southeast Yonkers
5.8 out of 10, (7 reviews)
"Everything about this place is amazing. Great location, very safe, cozy, clean. Will be back soon!"
United States
Paola
The price is AED 400
AED 995 total
includes taxes & fees
7 Aug - 8 Aug
NY Luxury Apt Free Parking in PRIME Area
Exterior

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (136 reviews)
"Great location, friendly and helpful staff. Good value for money."
United States
ian
The price is AED 547
AED 629 total
includes taxes & fees
19 Jul - 20 Jul
Stamford Suites
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

Hotel Nyack, a JdV by Hyatt Hotel

Hotel Nyack, a JdV by Hyatt Hotel

10/10 Excellent
"This is a super cool place to stay. The decor is nicely done, the restaurant is excellent and its walkable to main street attractions. We would stay here again if we were in the area."
sarkis 1-night trip
Posted 9 hours ago
Hotel Nyack, a JdV by Hyatt Hotel

Frequently asked questions

Can I find a vacation rental in Ossining?

Yes, there are vacation rentals in Ossining close to Labyrinth, or you can select a more remote option if you'd like a relaxing place to 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?

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!: This highly rated vacation home rental in Ossining is located near skiing and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in Ossining?

With 8 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 Kitchawan Preserve are a couple of picturesque spots to enjoy the outdoors. Sing Sing Correctional Facility and Hudson Hills Golf Course 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.