Title: Ossining Vacation Home Rentals from CA $558: Search Top Private Vacation Homes for Rent | Expedia.ca

  

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# Ossining Vacation Rentals

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## Check prices for these dates

Next weekend

[Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6190653&startDate=2025-10-10&endDate=2025-10-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6190653&startDate=2025-10-17&endDate=2025-10-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6190653&startDate=2025-10-31&endDate=2025-11-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[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)

## Browse Select Ossining Vacation Homes

![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)

![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)

![Pool](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/490a9125.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Ossining

8.8/10

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. "

CA $1,178

CA $1,965 total

includes taxes & fees

Oct 16 - Oct 17

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

![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)

![Interior](https://images.trvl-media.com/lodging/115000000/114610000/114606200/114606188/c1311c5e.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)

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

Greenwich

9.6/10

Exceptional

(15)

"Perfect place to rest. Excellent service! "

CA $94

CA $265 total

includes taxes & fees

Oct 9 - Oct 10

[](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)

![Interior](https://images.trvl-media.com/lodging/58000000/57350000/57343700/57343699/66144591.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)

![Casino](https://images.trvl-media.com/lodging/58000000/57350000/57343700/57343699/6073858e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Southeast Yonkers

8.0/10

Very good

(17)

"Great place great location"

CA $132

CA $188 total

includes taxes & fees

Oct 15 - Oct 16

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

![Interior](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/e5f1d678.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)

![TV](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/ee686000.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Highland Falls

10/10

Exceptional

(2)

"Good stay, awesome place"

CA $169

CA $525 total

includes taxes & fees

Oct 7 - Oct 8

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

![Luxury House | Private kitchen](https://images.trvl-media.com/lodging/104000000/103910000/103905100/103905054/7b65d74a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury House | Private kitchen](https://images.trvl-media.com/lodging/104000000/103910000/103905100/103905054/a39c5068.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury House | Bathroom](https://images.trvl-media.com/lodging/104000000/103910000/103905100/103905054/cd3a4fe3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury House | In-room dining](https://images.trvl-media.com/lodging/104000000/103910000/103905100/103905054/b1b24573.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury NY Home with Free Parking

White Plains

CA $466

CA $671 total

includes taxes & fees

Oct 8 - Oct 9

[](https://www.expedia.ca/White-Plains-Hotels-Luxury-NY-Home-With-Free-Parking.h103905054.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113960000/113954200/113954116/f6577739.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113960000/113954200/113954116/8d1f0403.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, video games, DVD player, books](https://images.trvl-media.com/lodging/114000000/113960000/113954200/113954116/d1898381.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113960000/113954200/113954116/d779e3f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Croton-on-Hudson

10/10

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."

CA $200

CA $444 total

includes taxes & fees

Oct 7 - Oct 8

[](https://www.expedia.ca/Croton-On-Hudson-Hotels-Croton-Quarters-Comfortable-Apt-With-Modern-Amenities-Near-Food.h113954116.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)

![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)

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

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

Highland Falls

10/10

Exceptional

(1)

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

CA $239

CA $681 total

includes taxes & fees

Oct 15 - Oct 16

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

![Living area](https://images.trvl-media.com/lodging/113000000/112370000/112364900/112364813/ebebe95b.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)

![Private kitchen](https://images.trvl-media.com/lodging/113000000/112370000/112364900/112364813/bdaff4ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Waterside

10/10

Exceptional

(4)

"Lovely little home in Stamford."

CA $244

CA $490 total

includes taxes & fees

Oct 13 - Oct 14

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

![Exterior](https://images.trvl-media.com/lodging/109000000/108480000/108478400/108478343/6b2d2281.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108480000/108478400/108478343/897509a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108480000/108478400/108478343/b8f28b41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/109000000/108480000/108478400/108478343/e8896e83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### West Point Family Retreat, 5 min walk to Thayer!

Highland Falls

9.6/10

Exceptional

(5)

"Nice houseAwesome kitchen Granddaughter loved the bunk bed and the many games"

CA $628

CA $1,154 total

includes taxes & fees

Oct 6 - Oct 7

[](https://www.expedia.ca/Highland-Falls-Hotels-West-Point-Family-Retreat.h108478343.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/115000000/114640000/114637300/114637256/62b642d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/115000000/114640000/114637300/114637256/2af87762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Blackout drapes, free WiFi](https://images.trvl-media.com/lodging/115000000/114640000/114637300/114637256/8a87cb23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/115000000/114640000/114637300/114637256/4675a87a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 3BR Prime Luxury near NYC w Arcade Room

Southeast Yonkers

8.0/10

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."

CA $836

CA $1,073 total

includes taxes & fees

Oct 6 - Oct 7

[](https://www.expedia.ca/Yonkers-Hotels-3BR-Prime-Luxury-Near-NYC-W-Arcade-Room.h114637256.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/118000000/117050000/117044300/117044255/97cfa196.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/118000000/117050000/117044300/117044255/744c8890.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117050000/117044300/117044255/8e7f9b62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/118000000/117050000/117044300/117044255/c5c2964c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Scarsdale

9.0/10

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. "

CA $237

CA $450 total

includes taxes & fees

Oct 6 - Oct 7

[](https://www.expedia.ca/Scarsdale-Hotels-Apartment-With-Kitchen-2-Sofa-Beds.h117044255.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)

![Property grounds](https://images.trvl-media.com/lodging/96000000/95630000/95621700/95621659/79b962d9.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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95630000/95621700/95621659/2a3d63c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 45 Minutes from NYC, Entire House near Stamford Downtown,

Downtown Stamford

10/10

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. "

CA $398

CA $740 total

includes taxes & fees

Oct 16 - Oct 17

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

![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)

![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)

### Fabulous 3bdrm Home w/parking!

Highland Falls

8.0/10

Very good

(2)

"Great place. Close to West Point activity. Clean and new."

CA $264

CA $426 total

includes taxes & fees

Oct 27 - Oct 28

[](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)

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

![Exterior](https://images.trvl-media.com/lodging/106000000/105180000/105177900/105177891/42150b1e.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)

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

Highland Falls

10/10

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!"

CA $268

CA $432 total

includes taxes & fees

Oct 15 - Oct 16

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

![Exterior](https://images.trvl-media.com/lodging/84000000/83720000/83719600/83719534/w1202h832x0y0-db000905.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/84000000/83720000/83719600/83719534/951a6af7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/84000000/83720000/83719600/83719534/f53f774c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83720000/83719600/83719534/9f3375a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cheerful Home in Yonkers NY

Lincoln Park

7.6/10

Good

(4)

"Nice neighborhood,open concept.Hreat space for my entire family.Kitchen big and spacious. Beds are huge. Definitely will stay here again."

CA $349

CA $823 total

includes taxes & fees

Oct 31 - Nov 1

[](https://www.expedia.ca/Yonkers-Hotels-Cheerful-Home-In-Yonkers-NY.h83719534.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/a7dbb900.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)

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

![Living area](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/8bc06f3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

 

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

Carmel Hamlet

9.8/10

Exceptional

(11)

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

CA $314

CA $587 total

includes taxes & fees

Oct 6 - Oct 7

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

![TV](https://images.trvl-media.com/lodging/92000000/92000000/91998600/91998590/a15ca564.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/92000000/91998600/91998590/cc196904.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/92000000/92000000/91998600/91998590/5b69a2fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/92000000/92000000/91998600/91998590/f9b4e67b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 3 Bd Home Pet Friendly, Parking and Laundry

Cove - East Side - Shippan

9.0/10

Wonderful

(2)

"the home was nice clean if in the area I would stay here again"

CA $409

CA $806 total

includes taxes & fees

Oct 12 - Oct 13

[](https://www.expedia.ca/Stamford-Hotels-Spacious-3-Bd-Home-Pet-Friendly.h91998590.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)

![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)

![TV, fireplace](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/3745699f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Contemporary Cozy Cottage

Lake Peekskill

10/10

Exceptional

(28)

"Very clean comfortable quiet place"

CA $314

CA $586 total

includes taxes & fees

Oct 6 - Oct 7

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69380000/69370900/69370899/48c22af9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69380000/69370900/69370899/6f125b69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69380000/69370900/69370899/09a62768.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/70000000/69380000/69370900/69370899/beda97cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

 

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

Cove - East Side - Shippan

8.6/10

Excellent

(7)

"Overall it was a good stay for my work team."

CA $600

CA $1,230 total

includes taxes & fees

Oct 12 - Oct 13

[](https://www.expedia.ca/Stamford-Hotels-The-Fred-Deluxe-7-BR-By-I95.h69370899.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/79000000/78410000/78400400/78400391/aebb609e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/79000000/78410000/78400400/78400391/acc8d6c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/79000000/78410000/78400400/78400391/5c5d3ca6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/79000000/78410000/78400400/78400391/c994d444.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

West Side

9.2/10

Wonderful

(5)

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

CA $366

CA $751 total

includes taxes & fees

Oct 7 - Oct 8

[](https://www.expedia.ca/Stamford-Hotels-Modern-3-Bdrm-Home-W-Parking.h78400391.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=2025-10-19&endDate=2025-10-20&regionId=6190653&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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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

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

### Best Western Paramus Hotel & Suites

10/10 Excellent

"Great breakfast"

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

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

### Windrose On Hudson

10/10 Excellent

"Nice clean room. Overnight stay because we were visiting friends."

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

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

### Amsterdam Hotel

10/10 Excellent

"Friendly. Accommodating. Ample parking. Quiet rooms. Some fixtures and surfaces are dated, but I knew this coming in. Great hotel for the price. "

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

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

### Ardsley Acres Hotel Westchester

10/10 Excellent

"They did a great job of renovating the property. By keep the night stay a little higher keeps the riff-raff out. Great place!! "

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

![Baymont by Wyndham White Plains - Elmsford](//images.trvl-media.com/lodging/1000000/10000/500/438/w8985h6000x10y0-9d556f34_y.jpg)

### Baymont by Wyndham White Plains - Elmsford

10/10 Excellent

"Everything was great, would have preferred a vent in the bathroom, otherwise I’m glad we stayed there and would stay again. "

[](https://expedia.ca/White-Plains-Hotels-La-Quinta-Inn-Suites-By-Wyndham-White-Plains-Elmsford.h438.Hotel-Information)

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

### Royal Regency Hotel

10/10 Excellent

"It’s a very convenient hotel"

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

![The Armon Stamford Hotel & Conference](//images.trvl-media.com/lodging/90000000/89820000/89818900/89818854/99ae042b_y.jpg)

### The Armon Stamford Hotel & Conference

10/10 Excellent

"What a wonderful two nights stay at this beautiful hotel, incredibly clean quiet by far one of the best places I’ve stayed at! "

[](https://expedia.ca/Stamford-Hotels-The-Armon-Hotel-Conference.h89818854.Hotel-Information)

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

### Hyatt Regency Greenwich

10/10 Excellent

"No"

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

![Armoni Inn & Suites](//images.trvl-media.com/lodging/1000000/20000/12100/12036/5f0c23aa_y.jpg)

### Armoni Inn & Suites

10/10 Excellent

"Good I like it"

[](https://expedia.ca/Orangeburg-Hotels-Armoni-Inn-Suites.h12036.Hotel-Information)

## Find out more about Ossining

## Ossining Vacation Homes information

| Number of reviews | 5 |
| --- | --- |
| Accommodation | 328 Vacation Homes |
| Lowest Price | CA $558 |
| Highest Price | CA $1,073 |

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