Title: Ossining Vacation Home Rentals : Search Top Private Vacation Homes for Rent | Expedia.ca

 

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![Main building at Maryknoll](https://images.trvl-media.com/place/3000449058/eaa5b59e-44e4-4686-a478-33459da1d8df.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by louann ohora

# Ossining Vacation Rentals

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## Check prices for these dates

Next weekend

[Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=6190653&startDate=2025-11-28&endDate=2025-11-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6190653&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6190653&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=6190653&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Ossining Vacation Homes

![House](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/ae91b214.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/05844142.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/6b001cf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/f49620ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Ossining

CA $619

CA $1,356 total

includes taxes & fees

Nov 25 - Nov 26

[](https://www.expedia.ca/Ossining-Hotels-Foliage-At-Westchester-Manor-Near-Sleepy-Hollow.h121520491.Hotel-Information)

![Outdoor banquet area](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/76b5d504.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor banquet area](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/df2c75ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/e858b8f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/fe2ef847.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Ossining

9.0/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Matthew W.

CA $842

CA $1,549 total

includes taxes & fees

Nov 25 - Nov 26

[](https://www.expedia.ca/Ossining-Hotels-Castle-Cozy-Winter-Wonderland-Events.h101852343.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/e73b5292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/424d87c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/339c4da4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/e5f1d678.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Highland Falls

10/10

Exceptional

(4)

"Good stay, awesome place"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Scott G.

CA $189

CA $564 total

includes taxes & fees

Dec 4 - Dec 5

[](https://www.expedia.ca/Highland-Falls-Hotels-House-On-The-Babbling-Brook-Quiet-2BR-King-Bed.h113522235.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/115000000/114610000/114606200/114606188/7ce63cd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/115000000/114610000/114606200/114606188/c1311c5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114610000/114606200/114606188/70b02142.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/115000000/114610000/114606200/114606188/71684fe5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Greenwich

9.6/10

Exceptional

(21)

"Perfect place to rest. Excellent service! "

![Mexico](https://a.travel-assets.com/egds/marks/flags/mx.svg)

Lucymar

CA $141

CA $327 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Greenwich-Hotels-2-Bedroom-And-1-Full-Bath-In-Lakeside-Home-With-Private-Dock.h114606188.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/58000000/57350000/57343700/57343699/f2e7ce71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/58000000/57350000/57343700/57343699/bb6ea792.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, Netflix](https://images.trvl-media.com/lodging/58000000/57350000/57343700/57343699/w1170h771x0y0-9623bf5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/58000000/57350000/57343700/57343699/66144591.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Southeast Yonkers

8.2/10

Very good

(18)

"Great place great location"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Daquan H.

CA $133

CA $190 total

includes taxes & fees

Nov 26 - Nov 27

[](https://www.expedia.ca/Yonkers-Hotels-Nice-Cozy-Room-By-Empire-City-Casino-And-Cross-County-Shopping-Center.h57343699.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/111000000/110990000/110986300/110986250/cf889632.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/111000000/110990000/110986300/110986250/2bdd6486.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110990000/110986300/110986250/04bc58ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/111000000/110990000/110986300/110986250/03441cf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Highland Falls

10/10

Exceptional

(2)

"Looked like this property was recently renovated. Very clean and nice. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ellie M.

CA $192

CA $607 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Highland-Falls-Hotels-Sleek-Escape-Modern-3-BR-4-Min-From-West-Point.h110986250.Hotel-Information)

![TV, fireplace](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/a7dbb900.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/393a7982.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining tables](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/eda946f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/1b0ced6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Carmel Hamlet

9.8/10

Exceptional

(12)

"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Hannah P.

CA $235

CA $500 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Carmel-Hotels-Lux-Bungalow-On-Gorgeous-Lake-Relax-Explore-Nearby-Towns-Ski-Kayak-Hike.h101941777.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522229/6b825ecf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522229/ff47ab00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522229/26c9de37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522229/8fad8a9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Highland Falls

9.0/10

Wonderful

(4)

"Excellent host, house is very clean. The queen and king beds are comfortable. The sound of the brook is relaxing. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Penny D.

CA $164

CA $605 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Highland-Falls-Hotels-3BR-West-Point-Retreat-3min-To-Back-Gate-King-Bed.h113522229.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/113000000/112370000/112364900/112364813/3138ca99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/113000000/112370000/112364900/112364813/2730f6d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112370000/112364900/112364813/880d2845.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/113000000/112370000/112364900/112364813/ebebe95b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Waterside

10/10

Exceptional

(7)

"Lovely little home in Stamford."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Pat A.

CA $247

CA $502 total

includes taxes & fees

Dec 4 - Dec 5

[](https://www.expedia.ca/Stamford-Hotels-Charming-2-Bedroom-House-In-Fabulous-Stamford-With-AC.h112364813.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/1ffbe7a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/116022ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/8cbcd139.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/26b38c44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Highland Falls

9.0/10

Wonderful

(4)

"Clean home, conveniently located to West Point. Very comfortable beds. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Danielle B.

CA $240

CA $437 total

includes taxes & fees

Dec 8 - Dec 9

[](https://www.expedia.ca/Highland-Falls-Hotels-Fabulous-3bdrm-Home-Wparking.h114378708.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/106000000/105180000/105177900/105177891/f4c5b854.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/106000000/105180000/105177900/105177891/599dbda5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105180000/105177900/105177891/e5c54a16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105180000/105177900/105177891/719e347a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Highland Falls

10/10

Exceptional

(7)

"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!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Molly s.

CA $302

CA $551 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Highland-Falls-Hotels-Lovely-3BR-Home-With-Parking-Walk-To-WP-Gate.h105177891.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/106000000/105780000/105770300/105770281/8513b943.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105780000/105770300/105770281/07a0a3fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/106000000/105780000/105770300/105770281/d8e2beef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105780000/105770300/105770281/978faccb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in River Edge

7.6/10

Good

(5)

"The stay was great. The host Kris is very communicative and easily accessible by text. The house was kept very clean and the amenities were great for our party. Would definitely visit again. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Abhi M.

[](https://www.expedia.ca/Paramus-Hotels-NJ-New-Construction-Luxury-Home-Minutes-To-NYC-Vacation-Or-Staycation.h105770281.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/96000000/95630000/95621700/95621659/41ac102f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95630000/95621700/95621659/7c5d6df1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach towels](https://images.trvl-media.com/lodging/96000000/95630000/95621700/95621659/220d7b45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/96000000/95630000/95621700/95621659/79b962d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Downtown Stamford

10/10

Exceptional

(19)

"Our hosts were very attentive and responsive with communications. The house is lovely, clean, well stocked and in a great location. We thoroughly enjoyed our stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Megan P.

CA $267

CA $581 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Stamford-Hotels-45-Minutes-From-NYC.h95621659.Hotel-Information)

![House](https://images.trvl-media.com/lodging/122000000/121910000/121901300/121901234/49103067.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/122000000/121910000/121901300/121901234/e36fc455.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/122000000/121910000/121901300/121901234/9a7fa637.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/122000000/121910000/121901300/121901234/b1ad31bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Cornwall

CA $1,343

CA $1,637 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Cornwall-Hotels-West-Point-Villa-Jacuzzi-Pool-BBQ-Games-Pets.h121901234.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/79000000/78410000/78400400/78400391/b41c748f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/79000000/78410000/78400400/78400391/a65c4dd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/79000000/78410000/78400400/78400391/2cce1da9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78410000/78400400/78400391/dfbd7e97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in West Side

9.4/10

Exceptional

(6)

"Place was clean, organized. A little odd to find but there was parking, the location felt safe. Would stay again."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Dave J.

CA $361

CA $755 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Stamford-Hotels-Modern-3-Bdrm-Home-W-Parking.h78400391.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/84000000/83930000/83925200/83925171/d7ec344a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, foosball, table tennis](https://images.trvl-media.com/lodging/84000000/83930000/83925200/83925171/1719048e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, foosball, table tennis](https://images.trvl-media.com/lodging/84000000/83930000/83925200/83925171/009311c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83930000/83925200/83925171/f114158e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Mahopac

10/10

Exceptional

(12)

"Super convenient location :)"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sean M.

CA $476

CA $1,026 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Mahopac-Hotels-Fun.h83925171.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/d9fd7f11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/32d0bc6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/c7d67b21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/eed0e9ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Lake Peekskill

10/10

Exceptional

(30)

"Very clean comfortable quiet place"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Mauro C.

CA $317

CA $592 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Lake-Peekskill-Hotels-Contemporary-Cozy-Cottage.h102145832.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/96000000/95770000/95764600/95764526/575b2a63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95770000/95764600/95764526/5526777a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95770000/95764600/95764526/838b94fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/96000000/95770000/95764600/95764526/6ea08c86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Tuckahoe

CA $550

CA $993 total

includes taxes & fees

Nov 28 - Nov 29

[](https://www.expedia.ca/Tuckahoe-Hotels-Comfortable-1-Family-Home-In-Tuckahoe-Thats-Near-Train.h95764526.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/123000000/122930000/122929100/122929001/bb90272b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122930000/122929100/122929001/570cd10d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/123000000/122930000/122929100/122929001/e249d080.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/123000000/122930000/122929100/122929001/e4b16d26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Cornwall

CA $305

CA $581 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Cornwall-Hotels-Storm-King-At-Narnia-Welcome-To-A-Slice-Of-Paradise-In-The-Hudson-Valley.h122929001.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/71000000/70590000/70580500/70580407/73215319.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, video-game console, books, offices](https://images.trvl-media.com/lodging/71000000/70590000/70580500/70580407/d5a3b5cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/71000000/70590000/70580500/70580407/ad7bdde0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/71000000/70590000/70580500/70580407/fe085224.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Cove - East Side - Shippan

10/10

Exceptional

(23)

"We loved how easily accessible and clean this property was. Super family friendly, lots of space. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kelley G.

CA $553

CA $1,200 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Stamford-Hotels-Stylish-Beach-Home-Near-Stamford-DowntownBeach.h70580407.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-07&endDate=2025-12-08&regionId=6190653&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

Black Friday Sale

Limited-time deals: save up to 50% on select hotels

[Book now](https://expedia.ca/deals?rfrr=AA_BF_PROMO_6190653)

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[Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FOssining-Private-Vacation-Homes.d6190653-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FOssining-Private-Vacation-Homes.d6190653-aaPrivateVacationHomes.Travel-Guide-Accommodation)

## Top Ossining Hotel Reviews

![Ramada by Wyndham Bronx](https://images.trvl-media.com/lodging/1000000/470000/462500/462463/c9951f9d_y.jpg)

### Ramada by Wyndham Bronx

10/10 Excellent

"Great place "

[](https://expedia.ca/New-York-Hotels-Ramada-By-Wyndham-Bronx.h462463.Hotel-Information)

![Hyatt Regency Greenwich](https://images.trvl-media.com/lodging/1000000/20000/18200/18180/19d28016_y.jpg)

### Hyatt Regency Greenwich

10/10 Excellent

"The room was clean and tidy, and the staff were very helpful and friendly. "

[](https://expedia.ca/Stamford-Hotels-Hyatt-Regency-Greenwich.h18180.Hotel-Information)

![Hyatt Place New York/Yonkers](https://images.trvl-media.com/lodging/11000000/10240000/10232200/10232108/w3837h2558x3y3-6fc198b6_y.jpg)

### Hyatt Place New York/Yonkers

10/10 Excellent

"Easy parking and good breakfast "

[](https://expedia.ca/White-Plains-Hotels-Hyatt-Place-New-YorkYonkers.h10232108.Hotel-Information)

![Ardsley Acres Hotel Westchester](https://images.trvl-media.com/lodging/2000000/1170000/1166900/1166864/4b305bf7_y.jpg)

### Ardsley Acres Hotel Westchester

10/10 Excellent

" Clean fresh rooms and friendly staff"

[](https://expedia.ca/White-Plains-Hotels-Ardsley-Acres-Hotel-Westchester.h1166864.Hotel-Information)

![Best Western Paramus Hotel & Suites](https://images.trvl-media.com/lodging/1000000/870000/869100/869030/8ee68b48_y.jpg)

### Best Western Paramus Hotel & Suites

10/10 Excellent

"Great stay"

[](https://expedia.ca/Paramus-Hotels-Best-Western-Paramus-Hotel-Suites.h869030.Hotel-Information)

![La Quinta Inn & Suites by Wyndham Stamford / New York City](https://images.trvl-media.com/lodging/1000000/30000/25000/24963/af81668d_y.jpg)

### La Quinta Inn & Suites by Wyndham Stamford / New York City

10/10 Excellent

"The staff was amazing "

[](https://expedia.ca/Stamford-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Stamford-New-York-City.h24963.Hotel-Information)

![Amsterdam Hotel](https://images.trvl-media.com/lodging/1000000/30000/20800/20793/f5bb9592_y.jpg)

### Amsterdam Hotel

10/10 Excellent

"Courteous and informative staff (even at 1:30 in the morning!). Quiet building. Plenty of free parking. Fridge & micro in the room. "

[](https://expedia.ca/Stamford-Hotels-Amsterdam-Hotel.h20793.Hotel-Information)

![Windrose On Hudson](https://images.trvl-media.com/lodging/113000000/112810000/112806700/112806652/f251141f_y.jpg)

### Windrose On Hudson

10/10 Excellent

"Amazing facility, very beautiful and clean, well kept! The staff was kind and helpful, and the views from the room were great. Perfect place for large parties or just a weekend getaway. Highly recommend!"

[](https://expedia.ca/Ossining-Hotels-Crotonville-Hotel.h112806652.Hotel-Information)

![Royal Regency Hotel](https://images.trvl-media.com/lodging/1000000/50000/40900/40814/c5903df6_y.jpg)

### Royal Regency Hotel

10/10 Excellent

"The best "

[](https://expedia.ca/White-Plains-Hotels-Royal-Regency-Hotel.h40814.Hotel-Information)

## Find out more about Ossining

## Ossining Vacation Homes information

| Number of reviews | |
| --- | --- |
| Accommodation | Vacation Homes |
| Lowest Price | |
| Highest Price | |

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