Best Apartments in Ossining, NY for Your Vacation from $206

A wooden boardwalk winding through a forest with autumn foliage.

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Our top choices for Ossining apartments

A covered area with exercise equipment, chairs, and a view through large windows.

1. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

Ossining

$246 nightly

Aug 23 - Aug 24

Total with taxes and fees

2. Polished 1BR w/ Accessible Room Features + Sauna

Ossining

"We could not find location in dark and rain. Only given GPS info and no name of hotel or property. Once we arrived guard at guardhouse could not assist as we could not affirm name. When finally able to track down contact info for the vacation property company that listed the rental they had to share hotel front desk info and that’s when we learned name was Windrose On Hudson. Very stressful situation- enjoyed historical location. Great facility, not so great TV/streaming set-up… cable. "

Nada S.

$268 nightly

Aug 23 - Aug 24

Total with taxes and fees

A dining table set with plates, cutlery, and glasses, with a bowl of fruit and a wine glass in the background.

3. Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

CROTON HDSN

Aimee S.

$326 nightly

Sep 2 - Sep 3

Total with taxes and fees

A modern living room with a stone fireplace, a leather sofa, a yellow armchair, a flat-screen TV, and a bookshelf.

4. 'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

Croton-on-Hudson

Mateo A.

$364 nightly

Aug 24 - Aug 25

Total with taxes and fees

A garden with a stone wall, a wooden fence, and a gravel path.

5. Piermont Oasis

Piermont

Megan D.

$189 nightly

Sep 7 - Sep 8

Total with taxes and fees

A modern kitchen with stainless steel appliances, white cabinetry, and a wooden floor.

6. Elegant Hideaway with Free Parking

White Plains

$308 nightly

Sep 2 - Sep 3

Total with taxes and fees

7. Cozy 1-bedroom retreat minutes from West Point!

Highland Falls

Zack C.

$187 nightly

Aug 23 - Aug 24

Total with taxes and fees

A stone staircase leading up to a house, surrounded by greenery and a blue tarp.

8. Garden Loft with Patios & Green Space · Westchester Retreat

Scarsdale

Henry C.

$305 nightly

Sep 2 - Sep 3

Total with taxes and fees

A wooden gazebo with a tiled roof at the top of a stone staircase surrounded by trees.

9. 2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

Greenwich

$297 nightly

Sep 7 - Sep 8

Total with taxes and fees

A dining table with a glass top, a vase with flowers, and a variety of pastries and fruits.

10. Prime Luxe 3-BR NYC - Free Parking

White Plains

$357 nightly

Sep 2 - Sep 3

Total with taxes and fees

11. 2 Mi to NYC Train: WFH-Friendly Greenwich Apt!

Greenwich

Ann E.

$305 nightly

Sep 7 - Sep 8

Total with taxes and fees

A modern kitchen with stainless steel appliances, a central island with chairs, and a window with a view.

12. Family-Friendly 3BR Home • Game Room • Free Parking • Minutes from NYC

White Plains

$460 nightly

Aug 23 - Aug 24

Total with taxes and fees

A wooden staircase leading to a gazebo in a forested area with a metal railing.

13. Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

Greenwich

"This was a warm and inviting space. CC even offered me breakfast. I was a single woman in for a class reunion and had be somewhere on Sat and Sunday mornings. It was lovely coming back to relax and read. The space is small perfect for a couple with a young person. The patio over looks the river. The house is on a cul-de-sac perfect for strolling around the neighborhood. Very quiet and safe. Well lit path at night to the back, private entrance. Small fridge but holds a lot. Microwave, kurgurg...

Kathleen W.

$202 nightly

Sep 1 - Sep 2

Total with taxes and fees

A modern living room with a sofa, a coffee table, and a TV mounted on the wall.

14. Charming 2-bedroom Apartment with AC in Yonkers

Bryn Mawr

$362 nightly

Aug 23 - Aug 24

Total with taxes and fees

A modern living room with a white sofa, a glass coffee table, and a flat-screen TV mounted on the wall.

15. NY Luxury Apt Free Parking in PRIME Area

Southeast Yonkers

Paola

$254 nightly

Aug 22 - Aug 23

Total with taxes and fees

A modern kitchen with stainless steel appliances, wooden cabinets, and a contemporary light fixture.

16. Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Highland Falls

Maria L.

$315 nightly

Aug 24 - Aug 25

Total with taxes and fees

A living room with a sofa, a glass coffee table, a fireplace, and a TV mounted above it.

17. Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Port Chester

Sarah W.

$352 nightly

Aug 25 - Aug 26

Total with taxes and fees

A wooden coffee table with two decorative planters in a living room.

18. Walk to WP Gate + Free Parking!

Highland Falls

Daniel C.

$315 nightly

Aug 24 - Aug 25

Total with taxes and fees

A modern living room with a sofa, a coffee table, and a bar stool.

19. Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Downtown Stamford

michelle b.

$279 nightly

Aug 25 - Aug 26

Total with taxes and fees

A living room with a sectional sofa, a white armchair, a patterned rug, and a wooden floor.

20. Spacious 3BR Luxe Escape near NYC

Southeast Yonkers

david

$356 nightly

Sep 2 - Sep 3

Total with taxes and fees

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Top Ossining Hotel Reviews

Royal Regency Hotel

10/10 Excellent

"Excellent. My third stay at this hotel."

Windrose On Hudson

8/10 Good

"The staff were very nice. The property was very interesting and large and has pretty patio areas and indoor sitting spots. The outdoor areas/trails need more attention, even though there was a fairly clear mowed and wooded path. There was no food available later in the evening, which was a problem when arriving around 9 PM, although they were allowing delivery services. They should at least have snacks for purchase at the front desk. When we found someone else’s takeout container under the bed when we were leaving/checking the room, the front desk gave us a free treat coupon for the nice breakfast spot on the property. They are trying very hard to get this place restarted, and I would go there again."

Find out more about Ossining

Ossining Apartments information

Number of reviews	215
Accommodation	396 Apartments
Lowest Price	$206
Highest Price	$526

Frequently asked questions

What's it like to stay at an apartment in Ossining?

There are plenty of places to stay in Ossining with 35 hotels and other lodging accommodations. Though there aren't many apartments, we can help you find accommodations that are similar. When you search for a place to stay on Expedia, you can filter by amenities you might find in an apartment like a kitchen. You can even filter by similar properties such as condos, vacation homes, or cottages. Make time to visit the region's favorite sights like Woodbury Common Premium Outlets.

Why would you choose an apartment versus a traditional hotel?

Often more spacious than a traditional hotel room, an apartment comes equipped with a kitchen, so you can cook some of your meals. Apartments are ideal for families who want the conveniences of home, and also for solo travelers who want to stay in a quieter area.

What's the top apartment for a stay in Ossining?

Listed below are some of the top apartments in the area to choose from: Uscale 2BR Escape in the Heart of NYC: Located in Yonkers, 15 mi/24.1 km from the heart of Ossining. Includes free WiFi. Access to free parking is available on site. Global Luxury Suites White Plains: Located 10.3 mi/16.6 km away in White Plains. Laundry facilities and free WiFi are included. Valet parking and a fitness center are on site. Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich: Located in Greenwich, 13.7 mi/22 km away. Includes separate dining areas. Access to onsite laundry facilities is available on site. Luxury 3BR Family Home Game Room Parking: Located 14.5 mi/23.3 km away in Yonkers. Amenities include free WiFi. Access to free parking is available on site. NY Luxury Apt Free Parking in PRIME Area: Located in Yonkers, 17.1 mi/27.5 km from Ossining. Includes free WiFi. Access to free parking is available on site.

What will the weather be like when I travel to Ossining?

Though weather is just one factor, it can really affect your travel plans, especially if you are planning a longer stay in Ossining. The hottest months are usually July and August with an average temp of 71°F, while the coldest months are January and February with an average of 34°F. Average annual precipitation for Ossining is 51 inches.

What should I see 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. While here, Sing Sing Correctional Facility and Ossining Public Library are other places worth a visit.

What's the best way to get to and around Ossining?

Knowing a bit about the transportation options can you save you a headache when you get to your destination. Fly into Westchester County Airport (HPN), which is located 10.5 mi (16.8 km) away from the heart of the city. Otherwise, look for flights into Teterboro, NJ (TEB), which is 23.9 mi (38.5 km) away. To venture out into the surrounding area, hop on a train at Ossining Station.

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Our top choices for Ossining apartments

1. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

2. Polished 1BR w/ Accessible Room Features + Sauna

3. Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food