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Ossining Holiday Rentals

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Our top choices for Ossining holiday rentals

2.0 star property
The price is NZ$617
includes taxes & fees
4 Jan - 5 Jan
1BR Queen near NYC | Trails, Biking & Sauna Bliss
2.0 star property
The price is NZ$1,502
includes taxes & fees
5 Jan - 6 Jan
Foliage at Westchester Manor - Near Sleepy Hollow
2.0 star property
The price is NZ$615
includes taxes & fees
4 Jan - 5 Jan
Polished 1BR w/ Accessible Room Features + Sauna

Aparthotel in Ossining

Near NYC! | Stylish Guestroom
2.0 star property
The price is NZ$645
includes taxes & fees
4 Jan - 5 Jan
Near NYC! | Stylish Guestroom

Aparthotel in Downtown Stamford

Stamford Suites
4.0 star property
6.2 out of 10, (84)
"Everything was good other than the two options for breakfast and housekeeping entering the hotel room unannounced or no knocking"
United States
Laila
The price is NZ$240
includes taxes & fees
21 Jan - 22 Jan
Stamford Suites

Aparthotel in West Norwalk

The Mansion Hotel-style
2.5 star property
8.2 out of 10, Very good, (22)
"Great service and very clean 👌 "
United States
JEAN
The Mansion Hotel-style
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 NZ$329
includes taxes & fees
2 Feb - 3 Feb
Cozy 1-bedroom retreat minutes from West Point!
10.0 out of 10, Exceptional, (5)
"Good stay, awesome place"
United States
Scott G.
The price is NZ$597
includes taxes & fees
4 Jan - 5 Jan
House on the Babbling Brook- Quiet 2BR + King Bed!
9.8 out of 10, Exceptional, (23)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is NZ$854
includes taxes & fees
3 Jan - 4 Jan
Walk-to-Lake Cottage With Office for Quiet Days and Easy Work
9.6 out of 10, Exceptional, (24)
"The hosts were very friendly and very accommodating. "
United States
Daniel C.
The price is NZ$451
includes taxes & fees
28 Jan - 29 Jan
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
9.8 out of 10, Exceptional, (12)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
The price is NZ$616
includes taxes & fees
5 Jan - 6 Jan
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
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 NZ$740
includes taxes & fees
5 Jan - 6 Jan
Sleek Escape: Modern 3 BR- 4 Min from West Point !
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 NZ$475
includes taxes & fees
5 Jan - 6 Jan
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
9.0 out of 10, Wonderful, (2)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
The price is NZ$482
includes taxes & fees
8 Jan - 9 Jan
Charming 1-bedroom apartment in Carmel with WiFi, AC
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.
The price is NZ$518
includes taxes & fees
4 Jan - 5 Jan
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
9.8 out of 10, Exceptional, (14)
"Great Unit."
United States
Rudy R.
The price is NZ$458
includes taxes & fees
5 Jan - 6 Jan
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Apartment in Brewster

The Hideaway
10.0 out of 10, Exceptional, (6)
"Me and my family stayed here for a quick get-away out of the city. Very pretty location, and loved our stay here! Thanks!"
United States
Rick C.
The price is NZ$550
includes taxes & fees
4 Jan - 5 Jan
The Hideaway
10.0 out of 10, Exceptional, (2)
"Great stay!"
United States
Ann S.
The price is NZ$411
includes taxes & fees
4 Jan - 5 Jan
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
9.8 out of 10, Exceptional, (90)
"I had a great stay at this extremely comfortable home in a quiet neighborhood. Maria was very welcoming and helpful. I hope to visit and stay here again soon."
United States
Jill D.
The price is NZ$465
includes taxes & fees
4 Jan - 5 Jan
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food

Apartment in Cove - East Side - Shippan

Seabreeze at the beach west beach Stamford ct.
9.8 out of 10, Exceptional, (10)
"Fantastic place Very clean, a perfect stay !!!"
United States
bill J.
The price is NZ$768
includes taxes & fees
6 Jan - 7 Jan
Seabreeze at the beach west beach Stamford ct.
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

Find out more about Ossining

Everything you need to know about Ossining holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Ossining holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Ossining holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Ossining holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Ossining. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Ossining holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Ossining holiday rentals we have selected for you start as low as NZ$240 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Ossining rentals

At Expedia, we put the best Ossining holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Ossining rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Ossining holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Ossining. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: This holiday home rental outside of Ossining 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 holiday rentals will I find in Ossining?

With 6 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.