Photo by Linda Zanetti

Ossining Holiday Rentals

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Holiday Rentals in Ossining

Summer Castle: Pool, Game Room, BBQ - Pet Friendly

8.0 out of 10, Very good, (3)
"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. "
The price is NZ$2,260
includes taxes & fees
21 July - 22 July
Summer Castle: Pool, Game Room, BBQ - Pet Friendly

Waterview House Walking Distance from Cove Beach

9.0 out of 10, Wonderful, (20)
"Easy entrance and exit policy. Great communication from owners. Perfect location. "
The price is NZ$1,990
includes taxes & fees
24 July - 25 July
Waterview House Walking Distance from Cove Beach

Stylish Beach Home near Stamford Downtown/Beach

10.0 out of 10, Exceptional, (20)
"Everything was great"
The price is NZ$2,700
includes taxes & fees
8 July - 9 July
Stylish Beach Home near Stamford Downtown/Beach

Spacious 3 Bd Home Pet Friendly, Parking and Laundry

9.0 out of 10, Wonderful, (2)
"the home was nice clean if in the area I would stay here again"
The price is NZ$952
includes taxes & fees
13 July - 14 July
Spacious 3 Bd Home Pet Friendly, Parking and Laundry

New Beach Home near Stamford Downtown/Shippan

10.0 out of 10, Exceptional, (21)
"Great home with fun ping pong table!"
The price is NZ$2,236
includes taxes & fees
5 July - 6 July
New Beach Home near Stamford Downtown/Shippan

The Luxury downtown. Pool Jim basketball

The price is NZ$425
includes taxes & fees
9 July - 10 July
The Luxury downtown. Pool Jim basketball

The Monroe | Elegant 2BR/2BA Downtown Stamford | Designed by Lavish & Live

The price is NZ$901
includes taxes & fees
6 July - 7 July
The Monroe | Elegant 2BR/2BA Downtown Stamford | Designed by Lavish & Live

Charming 2-bedroom house in fabulous Stamford with AC, WiFi

10.0 out of 10, Exceptional, (2)
"Lovely little home in Stamford."
The price is NZ$740
includes taxes & fees
17 July - 18 July
Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near...

9.2 out of 10, Wonderful, (5)
"Place was clean, organized. A little odd to find but there was parking, the location felt safe. Would stay again."
The price is NZ$1,035
includes taxes & fees
6 July - 7 July
Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near...

The West Lane Inn - Queen Room

9.4 out of 10, Exceptional, (3)
"Vert nice property, very nice and accommodating proprietor and staff."
The price is NZ$691
includes taxes & fees
10 July - 11 July
The West Lane Inn - Queen Room

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

9.0 out of 10, Wonderful, (4)
"Greeted with such kindness and care. Loved looking out over the lake and taking the canoe out in the morning and jumping in the lake! Hope we can stay there again soon. "
The price is NZ$549
includes taxes & fees
7 July - 8 July
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Family getaway.Commuter's Dream.Weddings&Events.Content House.Luxury Smart Home

10.0 out of 10, Exceptional, (1)
"Wow! I wish we could have stayed here more than just one night! The host was so accommodating of our last-minute reservation and provided friendly and thoughtful assistance throughout our stay. This home is stunning! Careful planning and top-of-the-line finishes clearly went into every detail of this beautiful family home and we were so comfortable in every space. Larchmont train station is just steps away and made our travel to NYC a breeze. The home truly has a park-like feel and the house is...
The price is NZ$2,632
includes taxes & fees
9 July - 10 July
Family getaway.Commuter's Dream.Weddings&Events.Content House.Luxury Smart Home

Luxury 3Bed Private Apartment Near Manhattan

9.0 out of 10, Wonderful, (18)
"Host was very accommodating and easy to communicate with!"
The price is NZ$1,114
includes taxes & fees
7 July - 8 July
Luxury 3Bed Private Apartment Near Manhattan

Upscale Relax near Yankee Stadium, and Columbia University "14 min drive"

2.0 out of 10, (1)
"The sheets were way over bleached and burned my skin. The bed is way too soft and the sofa is uneven and sinks. The area is quite scary especially at night, and it is surrounded by vacant lots and construction zones. Most of the other stores in this building are closed, and homeless people walking around. The cleaning products use have a distinctively bad smell that even the air conditioning couldn’t eliminate, and the air conditioners are so loud you can’t hear the tv if they are running."
The price is NZ$572
includes taxes & fees
18 July - 19 July
Upscale Relax near Yankee Stadium, and Columbia University "14 min drive"

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

9.8 out of 10, Exceptional, (7)
"Great spot, wonderful host. Would recommend to anyone!"
The price is NZ$695
includes taxes & fees
10 July - 11 July
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Luxury NY Home with Free Parking

4.0 star property
Luxury NY Home with Free Parking

Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

10.0 out of 10, Exceptional, (15)
"Wonderful, comfortable home! Clean, user-friendly with great views!"
The price is NZ$1,420
includes taxes & fees
6 July - 7 July
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

Comfortable 1 family home in Tuckahoe that's near train

The price is NZ$1,165
includes taxes & fees
4 July - 5 July
Comfortable 1 family home in Tuckahoe that's near train

TheVictorianBlue|25min to NYC

9.6 out of 10, Exceptional, (5)
"The accommodations were fantastic, with spacious rooms, modern amenities, and breathtaking views. Additionally, the host was incredibly accommodating, ensuring that every aspect of my stay was comfortable and enjoyable. I highly recommend this property to anyone looking for a perfect getaway with a gracious host!"
The price is NZ$2,395
includes taxes & fees
3 July - 4 July
TheVictorianBlue|25min to NYC

Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic

The price is NZ$529
includes taxes & fees
3 July - 4 July
Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic
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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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 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. Another good choice for your trip to Ossining is Summer Castle: Pool, Game Room, BBQ - Pet Friendly.

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.