A wooden boardwalk winding through a forest with autumn foliage.

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Our top choices for Ossining apartments

Interior

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

1BR Queen near NYC | Trails, Biking & Sauna Bliss
Ossining
The price is SAR 800
SAR 1,008 total
includes taxes & fees
20 Jul - 21 Jul
1BR Queen near NYC | Trails, Biking & Sauna Bliss
Interior

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 SAR 860
SAR 1,083 total
includes taxes & fees
19 Jul - 20 Jul
Polished 1BR w/ Accessible Room Features + Sauna
TV

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (3 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 SAR 525
SAR 930 total
includes taxes & fees
7 Jul - 8 Jul
Cozy 1-bedroom retreat minutes from West Point!
Property grounds

Piermont Oasis

Piermont Oasis
Piermont
9.8 out of 10, Exceptional, (18 reviews)
"Great place to stay! "
United States
Megan D.
The price is SAR 563
SAR 899 total
includes taxes & fees
29 Jul - 30 Jul
Piermont Oasis
TV

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (32 reviews)
"Super cute with everything we needed! We had a great time during our stay and this was the perfect spot for a little getaway! Highly recommend!"
United States
Christina
The price is SAR 826
SAR 1,550 total
includes taxes & fees
26 Jul - 27 Jul
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
2 bedrooms, iron/ironing board, WiFi, bed sheets

Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC

Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC
Bronx
9.8 out of 10, Exceptional, (26 reviews)
"Great sunny spacious and clean apartment for us to stay in when visiting family nearby. The hosts were super responsive whenever we had questions, and made our stay super seamless. Would definitely stay here again the next time we’re in town!"
United States
Lauren A.
The price is SAR 706
SAR 1,646 total
includes taxes & fees
7 Jul - 8 Jul
Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC
Offices

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 SAR 541
SAR 1,170 total
includes taxes & fees
14 Jul - 15 Jul
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Fridge, microwave, oven, stovetop

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 SAR 951
SAR 1,532 total
includes taxes & fees
7 Jul - 8 Jul
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Interior

The Tipsy Gypsy - Studio Apartment

The Tipsy Gypsy - Studio Apartment
Brewster
The price is SAR 563
SAR 1,034 total
includes taxes & fees
7 Jul - 8 Jul
The Tipsy Gypsy - Studio Apartment
Fridge, microwave, oven, stovetop

Stylish Home With Free ParkingZA

Stylish Home With Free ParkingZA
Glenbrook-Belltown
The price is SAR 860
SAR 1,254 total
includes taxes & fees
7 Jul - 8 Jul
Stylish Home With Free ParkingZA
Microwave, oven, stovetop

Serene 2-bedroom spacious apartment

Serene 2-bedroom spacious apartment
Carmel Hamlet
The price is SAR 657
SAR 1,261 total
includes taxes & fees
7 Jul - 8 Jul
Serene 2-bedroom spacious apartment
Dining

Romantic Hide Out

Romantic Hide Out
Waterside
3.0 out of 10, (2 reviews)
"Check-in was at 3 PM and I was unable to reach the host until 11 PM that night to gain access to the property. They never sent anything in advance. It was the most miserable experience I have ever had."
United States
Cheryl H.
The price is SAR 406
SAR 913 total
includes taxes & fees
12 Jul - 13 Jul
Romantic Hide Out
Smart TV

Modern Luxe 1BR Apt in Downtown Stamford

Modern Luxe 1BR Apt in Downtown Stamford
Downtown Stamford
9.6 out of 10, Exceptional, (5 reviews)
"Our family stayed in the hotel(s) next door. It was so nice to have our own personal space!"
United States
Jill G.
The price is SAR 541
SAR 1,575 total
includes taxes & fees
10 Jul - 11 Jul
Modern Luxe 1BR Apt in Downtown Stamford
Dining

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, (92 reviews)
"Our stay was just perfect! We chose the location based on being close-ish to family in northern Westchester and friends in the city and it was perfect. Maria is an excellent host and super attentive and helpful when needed. The apartment was the perfect size for our family and super cozy after a long day. We'd definitely stay again!"
United States
Aimee S.
The price is SAR 761
SAR 1,468 total
includes taxes & fees
21 Jul - 22 Jul
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
Interior

What's headline

What's headline
South Side
The price is SAR 676
SAR 2,313 total
includes taxes & fees
10 Jul - 11 Jul
What's headline
Fridge, microwave, oven, stovetop

Stylish Home and Cozy200

Stylish Home and Cozy200
Downtown Stamford
The price is SAR 1,044
SAR 1,491 total
includes taxes & fees
23 Jul - 24 Jul
Stylish Home and Cozy200
Smart TV, video games, DVD player, books

'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, (6 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 SAR 626
SAR 1,309 total
includes taxes & fees
7 Jul - 8 Jul
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Property grounds

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
7.6 out of 10, Good, (4 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 SAR 750
SAR 994 total
includes taxes & fees
14 Jul - 15 Jul
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Property grounds

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

2 Mi to NYC Train: WFH-Friendly Greenwich Apt!
Greenwich
2.0 out of 10, (1 review)
"No lock on the entrance door so I had to use the bed frame against it to act as a barrier. I was woken up one morning by the host and had to leave the apartment ASAP because the housing inspector was there and she hid all my belongings that I couldn’t fully locate afterwards. "
United States
Ann E.
The price is SAR 762
SAR 1,757 total
includes taxes & fees
7 Jul - 8 Jul
2 Mi to NYC Train: WFH-Friendly Greenwich Apt!
Luxury Apartment | Private kitchen

Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
The price is SAR 747
SAR 1,414 total
includes taxes & fees
1 Aug - 2 Aug
Elegant Hideaway with Free Parking
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

Westchester Marriott

Westchester Marriott

8/10 Good
"Staff was very accommodating, friendly and professional. It was as a pleasure to stay there."
Elizabeth 1-night trip
Posted 1 hour ago
Westchester Marriott

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 more popular 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. Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC: Located 19.8 mi/31.9 km away in Bronx. Amenities include Smart TVs. Elegant 2BR Modern Oasis Brand-New Build, Luxe Touches & Lightning-Fast WiFi, AC: Located in Bronx, 19.8 mi/31.9 km away. Includes Smart TVs. Access to onsite laundry facilities is available on site. Spacious 3BR Luxe Escape near NYC: 17.2 mi/27.6 km away in Yonkers. Amenities include free WiFi. Piermont Oasis: It's located in Piermont, 9.2 mi/14.8 km from Ossining. Includes private balconies and Smart TVs.
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 Depot Square and Teatown Lake Reservation are a couple of picturesque spots to enjoy the outdoors. While here, Sing Sing Correctional Facility and Hudson Hills Golf Course 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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