Photo by regina palmieri

Ossining Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Our top choices for Ossining vacation rentals

2.0 star property
The price is ¥44,827
¥57,676 total
includes taxes & fees
Jan 8 - Jan 9
1BR Queen near NYC | Trails, Biking & Sauna Bliss

Vacation Home in Ossining

NEW 45 Wolden Rd Ossining NY 10562
2.0 star property
The price is ¥47,223
¥125,879 total
includes taxes & fees
Jan 12 - Jan 13
NEW 45 Wolden Rd Ossining NY 10562
9.2 out of 10, Wonderful, (7)
"Communication was excellent. The house itself is older and fine for its age, but "
United States
Jonathan O.
The price is ¥68,125
¥141,901 total
includes taxes & fees
Jan 28 - Jan 29
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
2.0 star property
The price is ¥44,827
¥58,049 total
includes taxes & fees
Jan 9 - Jan 10
Polished 1BR w/ Accessible Room Features + Sauna

Aparthotel in Ossining

Near NYC! | Stylish Guestroom
2.0 star property
The price is ¥48,742
¥61,914 total
includes taxes & fees
Jan 9 - Jan 10
Near NYC! | Stylish Guestroom
10.0 out of 10, Exceptional, (3)
"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"
United States
Julio J.
The price is ¥15,660
¥64,273 total
includes taxes & fees
Jan 8 - Jan 9
Sleek Escape: Modern 3 BR- 4 Min from West Point !
10.0 out of 10, Exceptional, (5)
"Good stay, awesome place"
United States
Scott G.
The price is ¥13,155
¥50,456 total
includes taxes & fees
Jan 12 - Jan 13
House on the Babbling Brook- Quiet 2BR + King Bed!
9.8 out of 10, Exceptional, (15)
"Great Unit."
United States
Rudy R.
The price is ¥12,371
¥41,176 total
includes taxes & fees
Jan 12 - Jan 13
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
9.2 out of 10, Wonderful, (10)
"Great place to stay if you have a West Point student - super close to all West Point related activities. The place itself needs some work but it’s functional."
United States
Jesse C.
The price is ¥13,311
¥60,078 total
includes taxes & fees
Jan 12 - Jan 13
Local Artist Inspired | Walk to WestPoint + King Bed

Apartment in Bryn Mawr

Luxe 1BR Oasis - Prime NY Stay
2.0 star property
The price is ¥17,226
¥42,606 total
includes taxes & fees
Jan 22 - Jan 23
Luxe 1BR Oasis - Prime NY Stay
4.0 star property
Single Family 3BR Home Game Room Parking
10.0 out of 10, Exceptional, (1)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is ¥14,635
¥29,691 total
includes taxes & fees
Feb 2 - Feb 3
Cozy 1-bedroom retreat minutes from West Point!
10.0 out of 10, Exceptional, (2)
"Great stay!"
United States
Ann S.
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
9.6 out of 10, Exceptional, (24)
"The hosts were very friendly and very accommodating. "
United States
Daniel C.
The price is ¥20,085
¥41,422 total
includes taxes & fees
Jan 12 - Jan 13
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
10.0 out of 10, Exceptional, (6)
"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.
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

Apartment in Downtown Stamford

Modern Luxe 1BR Apt in Downtown Stamford
9.6 out of 10, Exceptional, (5)
"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 ¥21,141
¥57,120 total
includes taxes & fees
Jan 11 - Jan 12
Modern Luxe 1BR Apt in Downtown Stamford
2.0 star property
The price is ¥15,503
¥40,678 total
includes taxes & fees
Jan 22 - Jan 23
Luxury 1BR located in Prime Yonkers Area

Apartment in Downtown Stamford

Modern Luxury 1BR Stamford Getaway
10.0 out of 10, Exceptional, (1)
"The apartment is located in the hub bub of Stamford, a nice area very populated even in the evening where it feels safe. Apartment had all amenities that I needed. The host provided extra touches like a Keurig coffee pot stocked with Keurig cups and sugar. A washing machine and dryer were a plus as I like to pack only clean clothes. Bed was super comfortable. Modern design has a Zen vibe, great to decompress after travel. TV offered free movies that didn’t require my own subscription which...
United States
Debbie N.
The price is ¥25,839
¥49,133 total
includes taxes & fees
Jan 15 - Jan 16
Modern Luxury 1BR Stamford Getaway
10.0 out of 10, Exceptional, (5)
"Very nice property. We have a son at West Point and approximately an hour from New York City. Host was quick to respond to questions and provided excellent information. We will stay here again. "
United States
Mark V.
The price is ¥26,968
¥45,616 total
includes taxes & fees
Feb 4 - Feb 5
Beautiful First Flr, 2-Bedroom Apt w/ 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.
Save an average of 15% on thousands of hotels when you're signed in

Top Ossining Hotel Reviews

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
  • 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 vacation rental in Ossining?

Yes, there are vacation rentals close to well known attractions in Ossining, or you can go with a more remote 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's the top vacation rental that Ossining has to offer?

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: Visitors like this Ossining vacation home rental. It is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals will I find in Ossining?

With 6 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 Teatown Lake Reservation and Merchants Square are a couple of picturesque spots to enjoy the outdoors. Sing Sing Correctional Facility 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.