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Holiday Homes in Ossining

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Featured Holiday Homes in Ossining

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

8.8 out of 10, Excellent, (5)
"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$2,416
includes taxes & fees
16 Oct - 17 Oct
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

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

9.6 out of 10, Exceptional, (15)
"Perfect place to rest. Excellent service! "
The price is NZ$325
includes taxes & fees
9 Oct - 10 Oct
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Nice Cozy Room By Empire City Casino And Cross County Shopping Center

8.0 out of 10, Very good, (17)
"Great place great location"
The price is NZ$231
includes taxes & fees
15 Oct - 16 Oct
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

House on the Babbling Brook- Quiet 2BR + King Bed!

10.0 out of 10, Exceptional, (2)
"Good stay, awesome place"
The price is NZ$646
includes taxes & fees
7 Oct - 8 Oct
House on the Babbling Brook- Quiet 2BR + King Bed!

Luxury NY Home with Free Parking

4.0 star property
The price is NZ$825
includes taxes & fees
8 Oct - 9 Oct
Luxury NY Home with Free Parking

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

10.0 out of 10, Exceptional, (5)
"We had an excellent stay! Our hosts were kind and helpful. The home was modern and very well kept, very clean. I would highly recommend this location and home to anyone traveling in the area."
The price is NZ$546
includes taxes & fees
7 Oct - 8 Oct
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

Sleek Escape: Modern 3 BR- 4 Min from West Point !

10.0 out of 10, Exceptional, (1)
"Looked like this property was recently renovated. Very clean and nice. "
The price is NZ$837
includes taxes & fees
15 Oct - 16 Oct
Sleek Escape: Modern 3 BR- 4 Min from West Point !

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

10.0 out of 10, Exceptional, (4)
"Lovely little home in Stamford."
The price is NZ$602
includes taxes & fees
13 Oct - 14 Oct
Charming 2-bedroom house in fabulous Stamford with AC, WiFi

West Point Family Retreat, 5 min walk to Thayer!

2.0 star property
9.6 out of 10, Exceptional, (5)
"Nice houseAwesome kitchen Granddaughter loved the bunk bed and the many games"
The price is NZ$1,418
includes taxes & fees
7 Oct - 8 Oct
West Point Family Retreat, 5 min walk to Thayer!

3BR Prime Luxury near NYC w Arcade Room

2.0 star property
8.0 out of 10, Very good, (1)
"We thought we rented the entire property, but was half of it. expect a lot of stairs. No bath tubs but two showers. some door knobs and locks need maintenance, but overall nice clean rooms."
The price is NZ$1,319
includes taxes & fees
7 Oct - 8 Oct
3BR Prime Luxury near NYC w Arcade Room

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

9.0 out of 10, Wonderful, (2)
"The owner was very responsive and kind. The apartment was very clean and well updated. We are older adults and the access to the basement apartment was a bit of a challenge but the owner did graciously help with our luggage. The family does clearly disclose that they live above the unit and sounds of children may be heard. Between the sounds of the family above and the fact it’s a basement, not a “Loft”, with all the plumbing just above your head - it was not for us. "
The price is NZ$553
includes taxes & fees
7 Oct - 8 Oct
Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic

45 Minutes from NYC, Entire House near Stamford Downtown,

10.0 out of 10, Exceptional, (16)
"Very nice property. Owner was very nice and quickly answered any questions we had. Well stocked pantry and fridge!! We enjoyed our stay and property was very convenient and comfortable. "
The price is NZ$909
includes taxes & fees
16 Oct - 17 Oct
45 Minutes from NYC, Entire House near Stamford Downtown,

Fabulous 3bdrm Home w/parking!

8.0 out of 10, Very good, (2)
"Great place. Close to West Point activity. Clean and new."
The price is NZ$523
includes taxes & fees
27 Oct - 28 Oct
Fabulous 3bdrm Home w/parking!

Lovely 3BR Home with parking-Walk to WP Gate!

10.0 out of 10, Exceptional, (6)
"Easy booking, arrival, and departure. Very nice home. Very Clean and comfortable. Host was very kind and clear on everything for stay. Will book again!"
The price is NZ$531
includes taxes & fees
15 Oct - 16 Oct
Lovely 3BR Home with parking-Walk to WP Gate!

Cheerful Home in Yonkers NY

7.6 out of 10, Good, (4)
"Nice neighborhood,open concept.Hreat space for my entire family.Kitchen big and spacious. Beds are huge. Definitely will stay here again."
The price is NZ$1,010
includes taxes & fees
31 Oct - 1 Nov
Cheerful Home in Yonkers NY

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

9.8 out of 10, Exceptional, (11)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
The price is NZ$721
includes taxes & fees
8 Oct - 9 Oct
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

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$991
includes taxes & fees
12 Oct - 13 Oct
Spacious 3 Bd Home Pet Friendly, Parking and Laundry

Contemporary Cozy Cottage

10.0 out of 10, Exceptional, (28)
"Very clean comfortable quiet place"
The price is NZ$720
includes taxes & fees
7 Oct - 8 Oct
Contemporary Cozy Cottage

The Fred Deluxe 7 BR by I95, Train, HarborVw, Stamford Beaches & Workspace

8.6 out of 10, Excellent, (7)
"Overall it was a good stay for my work team."
The price is NZ$1,511
includes taxes & fees
12 Oct - 13 Oct
The Fred Deluxe 7 BR by I95, Train, HarborVw, Stamford Beaches & Workspace

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$923
includes taxes & fees
7 Oct - 8 Oct
Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near...
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

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Ossining Holiday Homes information

Number of reviews
5
Accommodation
364 Holiday Homes
Lowest Price
NZ$686
Highest Price
NZ$1,319