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
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Ossining holiday rentals

A modern kitchen with white cabinets, a stainless steel dishwasher, a black granite countertop, and a window with a view of trees.

1. Nyc-area Escape Near River, Trails & Mta!

Nyc-area Escape Near River, Trails & Mta!
3.0 star property
Ossining
The price is RM1,111
RM3,317 total
includes taxes & fees
15 Sept - 16 Sept
Nyc-area Escape Near River, Trails & Mta!
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.

2. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is RM2,682
RM5,020 total
includes taxes & fees
15 Sept - 16 Sept
Summer Pool Oasis Custom Bar Arcade Pool Table
A modern kitchen with stainless steel appliances, white cabinetry, and a wooden floor.

3. 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 RM729
RM1,440 total
includes taxes & fees
22 Sept - 23 Sept
Elegant Hideaway with 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.

4. 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 RM1,649
RM2,565 total
includes taxes & fees
15 Sept - 16 Sept
Luxury NYC Home with Free Parking for 12
A wooden gazebo with a tiled roof at the top of a stone staircase surrounded by trees.

5. 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 RM737
RM1,363 total
includes taxes & fees
30 Sept - 1 Oct
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
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.

6. 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 RM2,015
RM2,911 total
includes taxes & fees
27 Sept - 28 Sept
Luxury NYC Home Game Room 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 RM2,198
RM3,055 total
includes taxes & fees
15 Sept - 16 Sept
Prime Luxe 3-BR NYC - Free Parking
The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

8. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (174 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is RM648
RM745 total
includes taxes & fees
20 Sept - 21 Sept
Stamford Suites
A modern living room with a glass coffee table, teal sofa, and a television displaying a colorful scene.

9. 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 RM1,279
RM2,078 total
includes taxes & fees
2 Oct - 3 Oct
Uscale 2BR Escape in the Heart of NYC
A modern living room with a glass coffee table, teal sofa, and a television displaying a colorful scene.

10. 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 RM1,474
RM2,255 total
includes taxes & fees
30 Sept - 1 Oct
Luxury 3 BR Near NYC with Easy Parking
A modern living room with a sofa, armchairs, and a glass coffee table.

11. 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 RM2,381
RM3,271 total
includes taxes & fees
15 Sept - 16 Sept
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.

12. 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 RM1,279
RM2,037 total
includes taxes & fees
15 Sept - 16 Sept
Luxe 1BR Oasis - Prime NY Stay
A breakfast buffet with pastries, fruits, and a coffee station.

13. 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 RM3,663
RM4,687 total
includes taxes & fees
15 Sept - 16 Sept
3BR Prime Luxury NY - Free Parking
A living room with a sectional sofa, a white armchair, a patterned rug, and a wooden floor.

14. 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 RM1,649
RM2,451 total
includes taxes & fees
2 Oct - 3 Oct
Spacious 3BR Luxe Escape near 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.

15. 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 RM1,315
RM2,078 total
includes taxes & fees
2 Oct - 3 Oct
Luxury 1BR located in Prime Yonkers Area
A modern living room with a white sofa, a glass coffee table, and a marble-patterned rug.

16. Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking
3.5 star property
Southeast Yonkers
5.0 out of 10, (12 reviews)
"Though the privous occupants refused to vacate the property in time but the landlord was suupportive went out of their way and provided a refund option and an alternative...we took the alternative which happen to be better than the originally booked property ... Will use this management and property owner in our upcoming short terms rentals....."
United States
abdelwahab
The price is RM2,442
RM3,339 total
includes taxes & fees
15 Sept - 16 Sept
Modern Luxury Home w GameRoom & Parking
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
5.6 out of 10, (4 reviews)
"Beautiful layout. Property had everything that was needed for an awesome stay."
United States
Ashley
The price is RM1,151
RM1,894 total
includes taxes & fees
2 Oct - 3 Oct
Luxury 3BR Family Home Game Room Parking
A modern living room with a sofa, armchairs, a coffee table, and a dining area with a table and chairs.

18. Two Wash

Two Wash
2.0 star property
Bryn Mawr
The price is RM3,480
RM4,500 total
includes taxes & fees
15 Sept - 16 Sept
Two Wash
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.

19. 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 RM1,649
RM2,451 total
includes taxes & fees
2 Oct - 3 Oct
Spacious 3BR Luxe Escape near NYC
A modern kitchen with white cabinetry, a dining area with a glass table, and a view of the outdoors through large windows.

20. 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 RM1,649
RM2,451 total
includes taxes & fees
11 Oct - 12 Oct
Modern Comfort in the Heart of 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

Tarrytown House Estate

Tarrytown House Estate

10/10 Excellent
"Great place and staff would stay again"
DANIEL 1-night trip
Posted 7 hours ago
Tarrytown House Estate

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
  • Use the map to find apartments and other holiday homes in the Ossining neighbourhood you prefer
  • 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 in Ossining close to Labyrinth, 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.

What are some of the best holiday rentals that Ossining has to offer?

Modern Luxury Home w GameRoom & Parking: This holiday home rental outside Ossining 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 that you can cook with friends or family.

How many holiday rentals will I find in Ossining?

With 8 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 Merchants Square and Teatown Lake Reservation are a couple of picturesque spots to enjoy the outdoors. Ossining Public Library and Hudson Hills Golf Course 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.