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Vacation 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 ¥126,987
¥211,849 total
includes taxes & fees
Oct 16 - Oct 17
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, (17)
"Perfect place to rest. Excellent service! "
The price is ¥10,144
¥28,498 total
includes taxes & fees
Oct 9 - Oct 10
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 ¥14,201
¥20,263 total
includes taxes & fees
Oct 8 - Oct 9
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

West Point Family Retreat, 5 min walk to Thayer!

2.0 star property
9.8 out of 10, Exceptional, (6)
"Nice houseAwesome kitchen Granddaughter loved the bunk bed and the many games"
The price is ¥67,626
¥124,273 total
includes taxes & fees
Oct 8 - Oct 9
West Point Family Retreat, 5 min walk to Thayer!

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 ¥20,138
¥65,769 total
includes taxes & fees
Oct 8 - Oct 9
Sleek Escape: Modern 3 BR- 4 Min from West Point !

'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 ¥23,086
¥49,779 total
includes taxes & fees
Oct 13 - Oct 14
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

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 ¥25,548
¥48,472 total
includes taxes & fees
Oct 8 - Oct 9
Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic

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

10.0 out of 10, Exceptional, (5)
"Lovely little home in Stamford."
The price is ¥26,299
¥53,086 total
includes taxes & fees
Oct 19 - Oct 20
Charming 2-bedroom house in fabulous Stamford with AC, WiFi

45 Minutes from NYC, Entire House near Stamford Downtown,

10.0 out of 10, Exceptional, (17)
"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 ¥42,830
¥80,137 total
includes taxes & fees
Oct 16 - Oct 17
45 Minutes from NYC, Entire House near Stamford Downtown,

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 ¥28,876
¥46,501 total
includes taxes & fees
Oct 15 - Oct 16
Lovely 3BR Home with parking-Walk to WP Gate!

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 ¥90,018
¥115,585 total
includes taxes & fees
Oct 8 - Oct 9
3BR Prime Luxury near NYC w Arcade Room

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 ¥28,087
¥45,822 total
includes taxes & fees
Oct 27 - Oct 28
Fabulous 3bdrm Home w/parking!

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 ¥36,217
¥76,815 total
includes taxes & fees
Oct 8 - Oct 9
Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near...

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 ¥37,570
¥88,479 total
includes taxes & fees
Oct 31 - Nov 1
Cheerful Home in Yonkers NY

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

9.8 out of 10, Exceptional, (12)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
The price is ¥33,813
¥64,168 total
includes taxes & fees
Oct 15 - Oct 16
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 ¥36,217
¥77,266 total
includes taxes & fees
Oct 13 - Oct 14
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 ¥33,813
¥63,082 total
includes taxes & fees
Oct 8 - Oct 9
Contemporary Cozy Cottage

Stylish Beach Home near Stamford Downtown/Beach

10.0 out of 10, Exceptional, (22)
"Everything was great"
The price is ¥49,442
¥113,466 total
includes taxes & fees
Oct 13 - Oct 14
Stylish Beach Home near Stamford Downtown/Beach

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

10.0 out of 10, Exceptional, (17)
"We had a great stay and had everything we needed!"
The price is ¥67,491
¥130,146 total
includes taxes & fees
Oct 9 - Oct 10
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

3bedroom apartment in Teaneck with AC, WiFi, 12 miles from Times Square NYC.

The price is ¥27,050
¥62,596 total
includes taxes & fees
Oct 8 - Oct 9
3bedroom apartment in Teaneck with AC, WiFi, 12 miles from Times Square 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.
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Top Ossining Hotel Reviews

Find out more about Ossining

Find out more about Ossining

Ossining Vacation Homes information

Number of reviews
5
Accommodation
328 Vacation Homes
Lowest Price
¥60,103
Highest Price
¥115,585