Ossining Holiday Rentals

  • 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

In two weeks
In two months
In three months
In four months

Our top choices for Ossining holiday rentals

The price is HK$2,135
HK$2,738 total
includes taxes & fees
12 Feb - 13 Feb
1BR Queen near NYC | Trails, Biking & Sauna Bliss

Holiday Home in Ossining

NEW 45 Wolden Rd Ossining NY 10562
2.0 star property
The price is HK$3,915
HK$8,273 total
includes taxes & fees
23 Feb - 24 Feb
NEW 45 Wolden Rd Ossining NY 10562
9.2 out of 10, Wonderful, (7 reviews)
"Communication was excellent. The house itself is older and fine for its age, but "
United States
Jonathan O.
The price is HK$3,417
HK$7,222 total
includes taxes & fees
29 Jan - 30 Jan
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
The price is HK$2,135
HK$2,729 total
includes taxes & fees
12 Feb - 13 Feb
Polished 1BR w/ Accessible Room Features + Sauna

Aparthotel in Ossining

Near NYC! | Stylish Guestroom
The price is HK$2,330
HK$2,926 total
includes taxes & fees
12 Feb - 13 Feb
Near NYC! | Stylish Guestroom

Aparthotel in Downtown Stamford

Stamford Suites
4.0 star property
6.4 out of 10, (95 reviews)
"Nice clean rooms the bedding was comfortable, it smelled good walking in, I will be staying in this hotel in the next time I'm in Stamford."
United States
Fatima
The price is HK$1,017
HK$1,169 total
includes taxes & fees
2 Feb - 3 Feb
Stamford Suites
2.0 star property
The price is HK$772
HK$2,025 total
includes taxes & fees
2 Feb - 3 Feb
Luxury 1BR located in Prime Yonkers Area
10.0 out of 10, Exceptional, (6 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is HK$585
HK$2,557 total
includes taxes & fees
29 Jan - 30 Jan
House on the Babbling Brook- Quiet 2BR + King Bed!

Apartment in White Plains

Elegant Hideaway with Free Parking
2.0 star property
The price is HK$858
HK$2,143 total
includes taxes & fees
8 Feb - 9 Feb
Elegant Hideaway with Free Parking

Apartment in Bryn Mawr

Luxe 1BR Oasis - Prime NY Stay
2.0 star property
The price is HK$858
HK$2,121 total
includes taxes & fees
8 Feb - 9 Feb
Luxe 1BR Oasis - Prime NY Stay
10.0 out of 10, Exceptional, (1 review)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is HK$729
HK$1,470 total
includes taxes & fees
24 Feb - 25 Feb
Cozy 1-bedroom retreat minutes from West Point!
9.8 out of 10, Exceptional, (16 reviews)
"Great Unit."
United States
Rudy R.
The price is HK$585
HK$2,029 total
includes taxes & fees
29 Jan - 30 Jan
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Apartment in Southeast Yonkers

Spacious 3BR Luxe Escape near NYC
2.0 star property
The price is HK$1,552
HK$2,508 total
includes taxes & fees
9 Feb - 10 Feb
Spacious 3BR Luxe Escape near NYC
2.0 star property
The price is HK$1,170
HK$2,548 total
includes taxes & fees
8 Feb - 9 Feb
Uscale 2BR Escape in the Heart of NYC

Apartment in Bryn Mawr

Two Wash
2.0 star property
The price is HK$1,552
HK$2,898 total
includes taxes & fees
29 Jan - 30 Jan
Two Wash
9.6 out of 10, Exceptional, (25 reviews)
"Very kind host very comfortable rooms"
United States
brendan o.
The price is HK$835
HK$1,865 total
includes taxes & fees
10 Feb - 11 Feb
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
2.0 star property
The price is HK$1,552
HK$2,898 total
includes taxes & fees
4 Feb - 5 Feb
Luxury 3BR Family Home Game Room Parking
9.2 out of 10, Wonderful, (10 reviews)
"Everything was just as described. Very comfortable and welcoming. Easy communication and feedback. I would definitely stay again. "
United States
Jacquise H.
The price is HK$1,014
HK$2,848 total
includes taxes & fees
29 Jan - 30 Jan
Elegant 2BR Modern Oasis Brand-New Build, Luxe Touches & Lightning-Fast WiFi, AC
10.0 out of 10, Exceptional, (3 reviews)
"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 HK$1,014
HK$3,436 total
includes taxes & fees
4 Feb - 5 Feb
Sleek Escape: Modern 3 BR- 4 Min from West Point !
7.0 out of 10, Good, (16 reviews)
"It was very clean and in a great area. "
United States
Kyle
The price is HK$757
HK$1,444 total
includes taxes & fees
29 Jan - 30 Jan
Spacious & Cozy 1st Floor & Basement Apartment 15 min from 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.
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 holiday rental in Ossining?

Yes, there are holiday rentals close to the most popular sights in Ossining, 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?

Waterfront Retreat Center for Health & Wellness: This holiday home rental outside of Ossining is located by the ocean, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a terrace, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Ossining?

With 7 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 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 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.