A wooden boardwalk winding through a forest with autumn foliage.

Search Apartment Rentals in Ossining

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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

1BR Queen near NYC | Trails, Biking & Sauna Bliss
Ossining
The price is CA $328
CA $412 total
includes taxes & fees
Nov 15 - Nov 16
1BR Queen near NYC | Trails, Biking & Sauna Bliss
A covered area with exercise equipment, chairs, and a view through large windows.

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

Polished 1BR w/ Accessible Room Features + Sauna
Ossining
6.0 out of 10, (1 review)
"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. "
United States
Nada S.
The price is CA $328
CA $412 total
includes taxes & fees
Nov 15 - Nov 16
Polished 1BR w/ Accessible Room Features + Sauna
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

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
CROTON HDSN
9.8 out of 10, Exceptional, (93 reviews)
"The host, Maria, was excellent in staying in touch and personally met me upon check-in and checkout. The location is very convenient for walking around downtown or easily drive to nearby outings."
United States
Margaret S.
The price is CA $253
CA $517 total
includes taxes & fees
Nov 3 - Nov 4
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
A neatly made bed with a black and white duvet, a wooden headboard, and a bedside table with a lamp. There are three framed artworks on the wall above the bed.

4. 'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Croton-on-Hudson
10.0 out of 10, Exceptional, (3 reviews)
"Great stay!"
United States
Ann S.
The price is CA $220
CA $443 total
includes taxes & fees
Nov 1 - Nov 2
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
A modern living room with a stone fireplace, a leather sofa, a yellow armchair, a flat-screen TV, and a bookshelf.

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

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Croton-on-Hudson
10.0 out of 10, Exceptional, (9 reviews)
"We had an extended stay at Croton Quarters, it was great! The hosts truly are pet-friendly, the location is ideal, and the property comfortable for a longer term visit. "
United States
Mateo A.
The price is CA $322
CA $612 total
includes taxes & fees
Oct 27 - Oct 28
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
A motel with a blue awning and a '6 Now Open' sign.

6. 1 Queen Bed | Non-Smoking

1 Queen Bed | Non-Smoking
Elmsford
9.0 out of 10, Wonderful, (4 reviews)
"Short trip so just needed something quick, location near Westchester Airport suited us well."
United States
Anonymous traveller
The price is CA $158
CA $181 total
includes taxes & fees
Oct 22 - Oct 23
1 Queen Bed | Non-Smoking
A garden with a stone wall, a wooden fence, and a gravel path.

7. Piermont Oasis

Piermont Oasis
Piermont
9.6 out of 10, Exceptional, (23 reviews)
"Great place to stay! "
United States
Megan D.
The price is CA $170
CA $299 total
includes taxes & fees
Nov 3 - Nov 4
Piermont Oasis
A modern hotel lobby with a stone wall, a coffee machine, a refrigerator, and a sign advertising a motel.

8. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Elmsford
10.0 out of 10, Exceptional, (2 reviews)
"Our rooms felt cozy enough for two people with decent privacy due to separate bathrooms nearby too.The location suited our plan moving between airport runs & visits close by malls perfectly."
United States
Anonymous traveller
The price is CA $162
CA $185 total
includes taxes & fees
Oct 22 - Oct 23
1 King Bed | Non-Smoking
A hotel room with a bed, a desk, a chair, a TV, and a window with a curtain.

9. 1 Queen Bed | Smoking

1 Queen Bed | Smoking
Elmsford
10.0 out of 10, Exceptional, (1 review)
"Beds were adequate, nothing special but perfectly fine for a short overnight stay."
United States
Anonymous traveller
The price is CA $158
CA $181 total
includes taxes & fees
Oct 22 - Oct 23
1 Queen Bed | Smoking
A kitchenette with a water dispenser, microwave, coffee machine, and a snack vending machine.

10. 2 Full Beds | Non-Smoking

2 Full Beds | Non-Smoking
Elmsford
10.0 out of 10, Exceptional, (1 review)
"The staff were attentive without being pushy, and the bed provided good comfort."
United States
Anonymous traveller
The price is CA $166
CA $190 total
includes taxes & fees
Oct 22 - Oct 23
2 Full Beds | Non-Smoking
A modern kitchen with stainless steel appliances, white cabinetry, and a wooden floor.

11. 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 CA $254
CA $502 total
includes taxes & fees
Oct 20 - Oct 21
Elegant Hideaway with Free Parking
A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

12. Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.2 out of 10, Wonderful, (25 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
The price is CA $163
CA $437 total
includes taxes & fees
Oct 18 - Oct 19
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
A modern kitchen with a built-in oven, a large window, and a flat-screen TV mounted above the sink.

13. Luxury Urban Retreat + Spacious & Stylish

Luxury Urban Retreat + Spacious & Stylish
White Plains
The price is CA $495
CA $953 total
includes taxes & fees
Oct 20 - Oct 21
Luxury Urban Retreat + Spacious & Stylish
Living area

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

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
8.4 out of 10, Very good, (5 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is CA $162
CA $308 total
includes taxes & fees
Oct 19 - Oct 20
Cozy 1-bedroom retreat minutes from West Point!
A wooden staircase leading to a gazebo in a forested area with a metal railing.

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

Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Greenwich
8.4 out of 10, Very good, (6 reviews)
"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...
United States
Kathleen W.
The price is CA $319
CA $430 total
includes taxes & fees
Oct 18 - Oct 19
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
A modern kitchen with stainless steel appliances, wooden cabinets, and a contemporary light fixture.

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

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Location was perfect for West Point visit. The space was clean and recently updated, the beds very comfortable, and perfect layout and spacious for 3-4 people. The host was welcoming and responsive."
United States
Maria L.
The price is CA $292
CA $501 total
includes taxes & fees
Nov 16 - Nov 17
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
A modern living room with a sofa, a coffee table, and a bar stool.

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

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Downtown Stamford
9.2 out of 10, Wonderful, (11 reviews)
"loved walking the city. pizza was good."
United States
michelle b.
The price is CA $204
CA $448 total
includes taxes & fees
Oct 18 - Oct 19
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
A bedroom with a bed, a ceiling fan, a window, and a painting on the wall.

18. Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.4 out of 10, Exceptional, (20 reviews)
The price is CA $197
CA $650 total
includes taxes & fees
Nov 2 - Nov 3
Local Artist Inspired | Walk to WestPoint + King Bed
A hallway with a wooden door, a black table with a sign, and large green plants.

19. 3BR Near West Point | Coffee Bar | Sleeps 6

3BR Near West Point | Coffee Bar | Sleeps 6
Highland Falls
10.0 out of 10, Exceptional, (2 reviews)
"We had a great stay at Joseph’s home. The property was very clean, spacious, and well prepared for guests. My work team and I felt comfortable right away, and the house had everything we needed for both a productive and relaxing stay.Joseph was always kind, professional, and quick to respond, which made a big difference. I would recommend this property without hesitation."
United States
ROHID S.
The price is CA $193
CA $644 total
includes taxes & fees
Oct 21 - Oct 22
3BR Near West Point | Coffee Bar | Sleeps 6
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Ossining Hotel Reviews

Tarrytown House Estate

Tarrytown House Estate

10/10 Excellent
"Beautiful property, a comfortable bed, and delicious food."
Casey 1-night trip
Posted less than an hour ago
Tarrytown House Estate

Find out more about Ossining

Ossining Apartments information

Number of reviews
211
Accommodation
369 Apartments
Lowest Price
CA $181
Highest Price
CA $650

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: Global Luxury Suites White Plains: Located in White Plains, 10.3 mi/16.6 km from the heart of Ossining. Includes laundry facilities and free WiFi. Valet parking and a fitness center are on site. Uscale 2BR Escape in the Heart of NYC: Located 15 mi/24.1 km away in Yonkers. Amenities include free WiFi. Access to free parking is available on site. Luxury 3BR Family Home Game Room Parking: Located in Yonkers, 14.5 mi/23.3 km away. Includes free WiFi. Access to free parking is available on site. Spacious 3BR Luxe Escape near NYC: 17.2 mi/27.6 km away in Yonkers. Amenities include free WiFi. Charming 1-bedroom apt walk to Train and DownTown area with WiFi, AC: It's situated in Mamaroneck, 15.4 mi/24.8 km from Ossining.
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 Louis Engel Waterfront Park and Teatown Lake Reservation are a couple of picturesque spots to enjoy the outdoors. While here, Hudson Hills Golf Course and Thomas J. Watson Research Center 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.

Explore a world of travel with Expedia