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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Ossining vacation rentals

A spacious living room with a large window, a ceiling fan, a dining area with a table and chairs, and a staircase leading to an upper level.

1. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is P36,066
P71,408 total
includes taxes & fees
Nov 3 - Nov 4
Summer Pool Oasis Custom Bar Arcade Pool Table
A hallway with hardwood flooring, a staircase, and a dining area with a chair and table.

2. Snow Days & City Escapes: Spacious Ossining Home

Snow Days & City Escapes: Spacious Ossining Home
3.0 star property
Ossining
The price is P18,078
P52,093 total
includes taxes & fees
Oct 21 - Oct 22
Snow Days & City Escapes: Spacious Ossining Home
The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

3. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (187 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is P9,958
P11,452 total
includes taxes & fees
Oct 8 - Oct 9
Stamford Suites
A modern living room with a sectional sofa, a glass coffee table, and a marble rug. There are two wall art pieces and a potted plant.

4. 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 P30,963
P44,734 total
includes taxes & fees
Oct 5 - Oct 6
Luxury NYC Home Game Room Free Parking
A dining table with a variety of pastries and fruits, a vase with flowers, and a view of a brick wall and greenery outside.

5. 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, (2 reviews)
"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 P25,334
P39,412 total
includes taxes & fees
Oct 5 - Oct 6
Luxury NYC Home with Free Parking for 12
A modern kitchen with stainless steel appliances, white cabinetry, and a wooden floor.

6. Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
2.0 out of 10, (1 review)
The price is P11,203
P22,134 total
includes taxes & fees
Oct 5 - Oct 6
Elegant Hideaway with Free Parking
A dining table with a glass top, a vase with flowers, and a variety of pastries and fruits.

7. Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is P53,482
P68,886 total
includes taxes & fees
Oct 5 - Oct 6
Prime Luxe 3-BR NYC - Free Parking
A breakfast buffet with pastries, fruits, and a coffee station.

8. 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 P56,297
P72,021 total
includes taxes & fees
Oct 5 - Oct 6
3BR Prime Luxury NY - Free Parking
A living room with a leather sofa, a round coffee table, a bench, and a ceiling fan.

9. Updated Home w/ Patio Half Mile to West Point

Updated Home w/ Patio Half Mile to West Point
3.0 star property
Highland Falls
Updated Home w/ Patio Half Mile to West Point
A living room with a sectional sofa, a white armchair, a patterned rug, and a wooden floor.

10. Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
7.0 out of 10, Good, (4 reviews)
"My family and I were satisfy with the stay I’ll definitely coming back"
United States
Josephine
The price is P25,334
P37,662 total
includes taxes & fees
Oct 5 - Oct 6
Spacious 3BR Luxe Escape near NYC
A modern living room with a glass coffee table, teal sofa, and a television displaying a colorful scene.

11. Uscale 2BR Escape in the Heart of NYC

Uscale 2BR Escape in the Heart of NYC
2.0 star property
Bryn Mawr
9.0 out of 10, Wonderful, (2 reviews)
"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 P19,648
P31,927 total
includes taxes & fees
Oct 5 - Oct 6
Uscale 2BR Escape in the Heart of NYC
A modern kitchen with white cabinets, a central island with stools, a stone accent wall, a flat-screen TV, and a beige sofa with teal cushions.

12. 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 P20,211
P31,931 total
includes taxes & fees
Oct 5 - Oct 6
Luxury 1BR located in Prime Yonkers Area
A modern living room with a sofa, armchairs, and a glass coffee table.

13. 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 P36,593
P50,259 total
includes taxes & fees
Oct 5 - Oct 6
Luxury 5 BR Home Free Parking
A modern living room with a stone wall, a flat-screen TV, a white sofa, and a kitchen area with a bar counter and chairs.

14. Luxe 1BR Oasis - Prime NY Stay

Luxe 1BR Oasis - Prime NY Stay
2.0 star property
Bryn Mawr
2.0 out of 10, (2 reviews)
"My experience did not match the listing. I was asked to make payment outside the platform and the check-in process was not clear. I would not recommend this property. ⸻ ⭐⭐ Balanced Review The property did not meet expectations. When I arrived, the check-in process was unclear and the home appeared to be partially occupied. I was also instructed to make a payment outside of Hotels.com instead of using the platform. This caused confusion and concern. I would suggest the listing be...
United States
Dianelly
The price is P19,648
P31,301 total
includes taxes & fees
Oct 5 - Oct 6
Luxe 1BR Oasis - Prime NY Stay
A modern living room with a glass coffee table, teal sofa, and a television displaying a colorful scene.

15. 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 P22,644
P34,654 total
includes taxes & fees
Oct 5 - Oct 6
Luxury 3 BR Near NYC with Easy Parking
A modern living room with a sofa, armchairs, a coffee table, and a dining area with a table and chairs.

16. Two Wash

Two Wash
2.0 star property
Bryn Mawr
The price is P53,482
P69,153 total
includes taxes & fees
Oct 5 - Oct 6
Two Wash
A modern living room with a beige sectional sofa, a green armchair, a marble-patterned rug, a gold coffee table, and a flat-screen TV mounted on a white wall.

17. Luxury 3BR Family Home Game Room Parking

Luxury 3BR Family Home Game Room Parking
2.0 star property
Bryn Mawr
4.8 out of 10, (5 reviews)
"Beautiful layout. Property had everything that was needed for an awesome stay."
United States
Ashley
The price is P17,683
P29,103 total
includes taxes & fees
Oct 5 - Oct 6
Luxury 3BR Family Home Game Room Parking
A modern kitchen with white cabinetry, a dining area with a glass table, and a view of the outdoors through large windows.

18. 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 P25,334
P37,662 total
includes taxes & fees
Oct 7 - Oct 8
Modern Comfort in the Heart of NYC
A wooden gazebo with a tiled roof at the top of a stone staircase surrounded by trees.

19. 2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.5 star property
Greenwich
The price is P20,580
P31,586 total
includes taxes & fees
Oct 9 - Oct 10
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
A modern living room with a white sofa, a glass coffee table, and a round armchair. There is a wooden floor and a large window with curtains.

20. Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
2.0 out of 10, (3 reviews)
"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 P25,334
P37,662 total
includes taxes & fees
Oct 5 - Oct 6
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

Amsterdam Hotel

Amsterdam Hotel

10/10 Excellent
"We love this hotel! It is our "go to" place to stay when we are in the area. It's extremely affordable and clean. The staff is super friendly and helpful. Its also walking distance to the train station, we stayed here and took the train to NYC. Great stay!!"
Angie 1-night trip
Posted 1 hour ago
Amsterdam Hotel

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 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?

Modern Luxury Home w GameRoom & Parking: You might want to consider this Ossining vacation home rental for your stay. It is situated near the airport and has a rooftop terrace and free WiFi to help you feel content during your stay. It has 3 bedrooms as well as a kitchen with a full-sized fridge, a dishwasher, and a stovetop, so you can cook with friends or family.

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 Louis Engel Waterfront Park and Teatown Lake Reservation are a couple of picturesque spots to enjoy the outdoors. Hudson Hills Golf Course 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.