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Ossining Holiday Rentals

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Holiday Rentals in Ossining

Aparthotel in Ossining

2.0 star property
The price is AU$576
includes taxes & fees
30 Nov - 1 Dec
1BR Queen near NYC | Trails, Biking & Sauna Bliss

Holiday Home in Ossining

2.0 star property
The price is AU$1,545
includes taxes & fees
1 Dec - 2 Dec
Foliage at Westchester Manor - Near Sleepy Hollow

Holiday Home in Ossining

9.0 out of 10, Wonderful, (6)
"We booked the property because our family is growing too large for all of the children and grandchildren to spend the holidays together. The “holiday house” as our 4 year old coined it was the perfect place to spend Christmas and Hanukkah. Large yet cozy and very well appointed. All of our communication with proprietors was prompt and helpful, and they had the driveway salted and plowed within hours of the (very picturesque) snowfall the day before Christmas. I would happily book here again. "
United States
Matthew W.
The price is AU$2,138
includes taxes & fees
8 Dec - 9 Dec
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Aparthotel in Ossining

2.0 star property
The price is AU$598
includes taxes & fees
30 Nov - 1 Dec
Near NYC! | Stylish Guestroom

Aparthotel in Ossining

2.0 star property
The price is AU$574
includes taxes & fees
30 Nov - 1 Dec
Polished 1BR w/ Accessible Room Features + Sauna

Aparthotel in Norwalk

2.5 star property
8.4 out of 10, Very good, (14)
"Lovely property in a gorgeous setting. Staff were very responsive and welcoming. "
United States
Holly
The price is AU$173
includes taxes & fees
1 Dec - 2 Dec
The Mansion Hotel-style

Apartment in Highland Falls

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 AU$296
includes taxes & fees
2 Dec - 3 Dec
Cozy 1-bedroom retreat minutes from West Point!

Holiday Home in Greenwich

9.6 out of 10, Exceptional, (21)
"Perfect place to rest. Excellent service! "
Mexico
Lucymar
The price is AU$390
includes taxes & fees
1 Dec - 2 Dec
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Apartment in Greenwich

3.0 star property
The price is AU$354
includes taxes & fees
7 Dec - 8 Dec
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

Apartment in Highland Falls

10.0 out of 10, Exceptional, (13)
"Great Unit."
United States
Rudy R.
The price is AU$406
includes taxes & fees
30 Nov - 1 Dec
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Holiday Home in Highland Falls

10.0 out of 10, Exceptional, (2)
"Looked like this property was recently renovated. Very clean and nice. "
United States
Ellie M.
The price is AU$697
includes taxes & fees
3 Dec - 4 Dec
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Holiday Home in Highland Falls

10.0 out of 10, Exceptional, (5)
The price is AU$562
includes taxes & fees
30 Nov - 1 Dec
House on the Babbling Brook- Quiet 2BR + King Bed!

Holiday Home in Carmel Hamlet

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 AU$549
includes taxes & fees
30 Nov - 1 Dec
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Aparthotel in Downtown Stamford

4.0 star property
6.2 out of 10, (76)
"It was great"
United States
Natalie
The price is AU$211
includes taxes & fees
7 Dec - 8 Dec
Stamford Suites

Apartment in Cove - East Side - Shippan

9.8 out of 10, Exceptional, (9)
"Very nice! Easy to work with and house was what we expected. "
United States
Jack P.
The price is AU$579
includes taxes & fees
30 Nov - 1 Dec
Seabreeze at the beach west beach Stamford ct.

Apartment in Piermont

9.8 out of 10, Exceptional, (8)
"Carolyn was so amazing with her directions on how to park and check in. The apartment had everything as advertised. The ambiance was very private and peaceful. Walking distance to the town and pier. I would definitely stay again."
United States
Anonymous traveller
Piermont Oasis

Apartment in Greenwich

7.4 out of 10, Good, (3)
"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 AU$284
includes taxes & fees
1 Dec - 2 Dec
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

Aparthotel in Norwalk

The price is AU$203
includes taxes & fees
8 Dec - 9 Dec
MasterRoom with in Suit Bathroom

Apartment in Norwalk

3.0 star property
The price is AU$317
includes taxes & fees
30 Nov - 1 Dec
Gold Coast Getaway! Upscale Apt Near New Canaan

Apartment in Getty Square

2.0 star property
The price is AU$551
includes taxes & fees
7 Dec - 8 Dec
Cozy Apartment to Relax - Apartment "A"
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 favourite 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 depend 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 AU$210 per night. Entering your travel dates in the search wizard might find you 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?

3BR Prime Luxury near NYC w Arcade Room: This holiday home rental outside of Ossining is near the airport and offers free WiFi to help you feel perfectly comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

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 Kitchawan Preserve 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.