Title: Ossining Vacation Rentals from CA $188: Short-Term Rentals for 2026 | Expedia.ca

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![](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

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

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## Check prices for these dates

In two weeks

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=6190653&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=6190653&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 26 - Jun 28](https://www.expedia.ca/Hotel-Search?regionId=6190653&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 24 - Jul 26](https://www.expedia.ca/Hotel-Search?regionId=6190653&startDate=2026-07-24&endDate=2026-07-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Ossining vacation rentals

![Outdoor banquet area](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/05588dfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/f958fa55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/6407ae3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/0ca0a1f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Ossining-Hotels-Castle-Retreat-W-Pool.h101852343.Hotel-Information)

Ossining

9.2/10

Wonderful

(7 reviews)

"Super fun location! Host was very helpful. The house is very comfortable for large groups "

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

natalie l.

CA $562

CA $1,233 total

includes taxes & fees

Apr 7 - Apr 8

[](https://www.expedia.ca/Ossining-Hotels-Castle-Retreat-W-Pool.h101852343.Hotel-Information)

![Villa](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/6e503ed4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Villa](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/b0adc70f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Villa](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/w3000h1944x0y0-bf620bb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### Westchester Summer Pool Pet Friendly Events Games

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

Ossining

CA $697

CA $1,421 total

includes taxes & fees

Apr 8 - Apr 9

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

![Interior](https://images.trvl-media.com/lodging/122000000/121190000/121182500/121182497/c8911274.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, foosball, offices](https://images.trvl-media.com/lodging/122000000/121190000/121182500/121182497/7a3d82db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/122000000/121190000/121182500/121182497/e72867a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/122000000/121190000/121182500/121182497/e7b14123.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1BR Queen near NYC | Trails, Biking & Sauna Bliss

[](https://www.expedia.ca/Ossining-Hotels-1BR-Queen-Near-NYC-Trails.h121182497.Hotel-Information)

Ossining

CA $368

CA $467 total

includes taxes & fees

May 3 - May 4

[](https://www.expedia.ca/Ossining-Hotels-1BR-Queen-Near-NYC-Trails.h121182497.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/122000000/121190000/121182500/121182499/d63a6691.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, foosball, offices](https://images.trvl-media.com/lodging/122000000/121190000/121182500/121182499/b1ec5991.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/122000000/121190000/121182500/121182499/7a4af8d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/122000000/121190000/121182500/121182499/60fba9ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Near NYC! | Stylish Guestroom

[](https://www.expedia.ca/Ossining-Hotels-Near-NYC-Stylish-Guestroom.h121182499.Hotel-Information)

Ossining

CA $404

CA $513 total

includes taxes & fees

May 3 - May 4

[](https://www.expedia.ca/Ossining-Hotels-Near-NYC-Stylish-Guestroom.h121182499.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/122000000/121190000/121182600/121182502/5a24bb82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/122000000/121190000/121182600/121182502/ea876890.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, foosball, offices](https://images.trvl-media.com/lodging/122000000/121190000/121182600/121182502/9a62d3ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/122000000/121190000/121182600/121182502/f51e4cd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Polished 1BR w/ Accessible Room Features + Sauna

[](https://www.expedia.ca/Ossining-Hotels-Polished-1BR-W-Accessible-Room-Features-Sauna.h121182502.Hotel-Information)

Ossining

6.0/10

(1 review)

"We could not find location in dark and rain. Only given GPS info and no name of hotel or property. Once we arrived guard at guardhouse could not assist as we could not affirm name. When finally able to track down contact info for the vacation property company that listed the rental they had to share hotel front desk info and that’s when we learned name was Windrose On Hudson. Very stressful situation- enjoyed historical location. Great facility, not so great TV/streaming set-up… cable. "

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

Nada S.

CA $399

CA $509 total

includes taxes & fees

May 3 - May 4

[](https://www.expedia.ca/Ossining-Hotels-Polished-1BR-W-Accessible-Room-Features-Sauna.h121182502.Hotel-Information)

![Villa, Garden View | Living area](https://images.trvl-media.com/lodging/124000000/123350000/123346400/123346355/9a2b218a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Villa, Garden View](https://images.trvl-media.com/lodging/124000000/123350000/123346400/123346355/846b4d95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/124000000/123350000/123346400/123346355/3ffc94b7_edited_7c06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/124000000/123350000/123346400/123346355/279d1dca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury NYC Home Game Room Free Parking

[](https://www.expedia.ca/White-Plains-Hotels-Luxury-NYC-Home-Game-Room-Free-Parking.h123346355.Hotel-Information)

White Plains

CA $370

CA $630 total

includes taxes & fees

Apr 7 - Apr 8

[](https://www.expedia.ca/White-Plains-Hotels-Luxury-NYC-Home-Game-Room-Free-Parking.h123346355.Hotel-Information)

![Luxury Apartment | Living area](https://images.trvl-media.com/lodging/124000000/123950000/123949500/123949488/7f7cce63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Apartment](https://images.trvl-media.com/lodging/124000000/123950000/123949500/123949488/e2ee5d10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Apartment | Bathroom](https://images.trvl-media.com/lodging/124000000/123950000/123949500/123949488/4c884e5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/124000000/123950000/123949500/123949488/b90b764e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury 1BR located in Prime Yonkers Area

[](https://www.expedia.ca/Yonkers-Hotels-JayZero.h123949488.Hotel-Information)

Bryn Mawr

10/10

Exceptional

(2 reviews)

"Everything was clean, good communication.. I would like to come back again for sure "

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

Genesis

CA $126

CA $348 total

includes taxes & fees

Apr 19 - Apr 20

[](https://www.expedia.ca/Yonkers-Hotels-JayZero.h123949488.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)

![Exterior](https://images.trvl-media.com/lodging/115000000/114610000/114606200/114606188/e1560e45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/115000000/114610000/114606200/114606188/5b614a2b.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)

### 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

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

Greenwich

9.8/10

Exceptional

(29 reviews)

"Beautiful space, excellent communication from the hosts. Would stay again!"

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

Crystal

CA $187

CA $385 total

includes taxes & fees

Apr 8 - Apr 9

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

![Luxury Apartment | Living area](https://images.trvl-media.com/lodging/106000000/105360000/105358700/105358651/df26ff7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Apartment | Bathroom](https://images.trvl-media.com/lodging/106000000/105360000/105358700/105358651/324aa83c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Apartment | Private kitchen](https://images.trvl-media.com/lodging/106000000/105360000/105358700/105358651/634ccf4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105360000/105358700/105358651/bdb4c2f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury 3 BR Near NYC with Easy Parking

[](https://www.expedia.ca/Yonkers-Hotels-Luxury-3-BR-Near-NYC-With-Easy-Parking.h105358651.Hotel-Information)

Bryn Mawr

CA $330

CA $577 total

includes taxes & fees

Apr 7 - Apr 8

[](https://www.expedia.ca/Yonkers-Hotels-Luxury-3-BR-Near-NYC-With-Easy-Parking.h105358651.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)

![Casino](https://images.trvl-media.com/lodging/58000000/57350000/57343700/57343699/6073858e.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/c4157729.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/58000000/57350000/57343700/57343699/9101db47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Southeast Yonkers

8.2/10

Very good

(18 reviews)

"Great location"

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

Jordan S.

CA $132

CA $188 total

includes taxes & fees

Apr 7 - Apr 8

[](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/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/bdaff4ee.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/ac1bba42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

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

Waterside

10/10

Exceptional

(11 reviews)

"Fantastic place. We had a great stay!"

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

Sara C.

CA $225

CA $472 total

includes taxes & fees

Apr 14 - Apr 15

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

![Property grounds](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/3a9ea66f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/c55e3667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/dfec5e09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/5ed95c10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

[](https://www.expedia.ca/Fort-Montgomery-Hotels-Serene-Mountain-Top-Views-Overlooking-Hudson-River-And-Surrounding-Highlands.h34345199.Hotel-Information)

Fort Montgomery

9.8/10

Exceptional

(134 reviews)

"Amazing place Thanks for the stay "

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

Julien C.

CA $262

CA $378 total

includes taxes & fees

Apr 7 - Apr 8

[](https://www.expedia.ca/Fort-Montgomery-Hotels-Serene-Mountain-Top-Views-Overlooking-Hudson-River-And-Surrounding-Highlands.h34345199.Hotel-Information)

![Offices](https://images.trvl-media.com/lodging/103000000/102690000/102683600/102683510/3f00e9fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102690000/102683600/102683510/a391c77a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/103000000/102690000/102683600/102683510/e7877d24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102690000/102683600/102683510/b60310aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

[](https://www.expedia.ca/Stamford-Hotels-Luxury-1BR-Apartment-In-Downtown-Stamford-W-Amenities-Easy-Access-To-NYC.h102683510.Hotel-Information)

Downtown Stamford

9.2/10

Wonderful

(11 reviews)

"Perfect apartment and location. Amazing communication. Thank you!!"

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

Ryan F.

CA $201

CA $436 total

includes taxes & fees

Apr 9 - Apr 10

[](https://www.expedia.ca/Stamford-Hotels-Luxury-1BR-Apartment-In-Downtown-Stamford-W-Amenities-Easy-Access-To-NYC.h102683510.Hotel-Information)

![TV, fireplace](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/38809636.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/416c2b95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/cfa82cec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/07a03d02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Carmel Hamlet

9.8/10

Exceptional

(13 reviews)

"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 $282

CA $555 total

includes taxes & fees

Apr 7 - Apr 8

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

![Luxury Duplex | Living area](https://images.trvl-media.com/lodging/125000000/124100000/124092300/124092283/d15d0e0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Duplex](https://images.trvl-media.com/lodging/125000000/124100000/124092300/124092283/9f98c14a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Duplex | Private kitchen](https://images.trvl-media.com/lodging/125000000/124100000/124092300/124092283/778362e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124100000/124092300/124092283/02854c32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Uscale 2BR Escape in the Heart of NYC

[](https://www.expedia.ca/Yonkers-Hotels-Uscale-2BR-Escape-In-The-Heart-Of-NYC.h124092283.Hotel-Information)

Bryn Mawr

8.0/10

Very good

(1 review)

"The house was very clean and the areas was quiet too. We had a nice spot to park the car. The staff was calling and checking on me if I didn’t have any issues with the check in. They were available all the time. The only thing we will need next time if possible is the washer and dryer and extra towels because we were 5 and only got 3 towels. But overall we enjoyed the stays."

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

Adj Fatou

CA $244

CA $495 total

includes taxes & fees

Apr 7 - Apr 8

[](https://www.expedia.ca/Yonkers-Hotels-Uscale-2BR-Escape-In-The-Heart-Of-NYC.h124092283.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/424d87c9.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)

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

![TV](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/9832ea44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Highland Falls

10/10

Exceptional

(8 reviews)

"Good stay, awesome place"

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

Scott G.

CA $177

CA $550 total

includes taxes & fees

Apr 8 - Apr 9

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

![Private kitchen](https://images.trvl-media.com/lodging/111000000/110790000/110784600/110784547/320bd4a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110790000/110784600/110784547/a4d2d147.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, towels, soap, toilet paper](https://images.trvl-media.com/lodging/111000000/110790000/110784600/110784547/2a0deaa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/111000000/110790000/110784600/110784547/be0aeba4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 1-bedroom apartment in Carmel with WiFi, AC

[](https://www.expedia.ca/Carmel-Hotels-Charming-1-Bedroom-Apartment-In-Carmel-With-WiFi.h110784547.Hotel-Information)

Carmel Hamlet

9.0/10

Wonderful

(2 reviews)

"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "

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

Emmett

CA $188

CA $387 total

includes taxes & fees

Apr 7 - Apr 8

[](https://www.expedia.ca/Carmel-Hotels-Charming-1-Bedroom-Apartment-In-Carmel-With-WiFi.h110784547.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/92000000/91400000/91391400/91391396/13d8fc7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/92000000/91400000/91391400/91391396/0f1e7af8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91400000/91391400/91391396/1c766ca2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/92000000/91400000/91391400/91391396/99922af1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Walk-to-Lake Cottage With Office for Quiet Days and Easy Work

[](https://www.expedia.ca/Putnam-Valley-Hotels-Walk-To-Lake-Cottage-With-Office-For-Quiet-Days-And-Easy-Work.h91391396.Hotel-Information)

Putnam Valley

9.8/10

Exceptional

(23 reviews)

"Great, clean house, nice accommodating host. Would stay here again. "

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

Heather T.

CA $258

CA $712 total

includes taxes & fees

Apr 8 - Apr 9

[](https://www.expedia.ca/Putnam-Valley-Hotels-Walk-To-Lake-Cottage-With-Office-For-Quiet-Days-And-Easy-Work.h91391396.Hotel-Information)

![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/103000000/102150000/102145900/102145832/3745699f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/e5a3641b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/449fc3a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Contemporary Cozy Cottage

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

Lake Peekskill

9.8/10

Exceptional

(32 reviews)

"Very clean comfortable quiet place"

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

Mauro C.

CA $314

CA $590 total

includes taxes & fees

Apr 7 - Apr 8

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

![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/95000000/94720000/94717500/94717464/dd930402.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/95000000/94720000/94717500/94717464/328adef2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/95000000/94720000/94717500/94717464/1cd6d553.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/95000000/94720000/94717500/94717464/2c8ccdec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

[](https://www.expedia.ca/Highland-Falls-Hotels-Quiet-Apt-With-Coffee-Bar.h94717464.Hotel-Information)

Highland Falls

9.8/10

Exceptional

(18 reviews)

"Great Unit."

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

Rudy R.

CA $160

CA $428 total

includes taxes & fees

Apr 8 - Apr 9

[](https://www.expedia.ca/Highland-Falls-Hotels-Quiet-Apt-With-Coffee-Bar.h94717464.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.

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## Find vacation rentals that suit your style

Villas

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Cottages

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Private vacation homes

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Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Ossining%2C+New+York%2C+United+States+of+America&regionId=6190653&latLong=41.162872%2C-73.861526&adults=2&startDate=2026-07-04&d1=2026-07-04&endDate=2026-07-07&d2=2026-07-07&lodging=APARTMENT)

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Ossining%2C+New+York%2C+United+States+of+America&regionId=6190653&latLong=41.162872%2C-73.861526&adults=2&startDate=2026-07-04&d1=2026-07-04&endDate=2026-07-07&d2=2026-07-07&lodging=APART_HOTEL)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Ossining%2C+New+York%2C+United+States+of+America&regionId=6190653&latLong=41.162872%2C-73.861526&adults=2&startDate=2026-07-04&d1=2026-07-04&endDate=2026-07-07&d2=2026-07-07&lodging=CABIN)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Ossining%2C+New+York%2C+United+States+of+America&regionId=6190653&latLong=41.162872%2C-73.861526&adults=2&startDate=2026-07-04&d1=2026-07-04&endDate=2026-07-07&d2=2026-07-07&lodging=CONDO)

Residences

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## Top Ossining Hotel Reviews

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

### Royal Regency Hotel

8/10 Good

"Hotel overall was good for a quick stop. Little road noise from the far end of the building. Shower needs a good scrub down. The best part was the breakfast! It was great and had everything you need to start your day. "

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

![Tarrytown House Estate](https://images.trvl-media.com/lodging/1000000/50000/49700/49674/b7afffa4_y.jpg)

### Tarrytown House Estate

8/10 Good

"The staff at breakfast would serve the coffee once and rarely came to fill up the cups unless we asked. I feel that there is staff shortage."

[](https://expedia.ca/White-Plains-Hotels-Tarrytown-House-Estate-On-The-Hudson.h49674.Hotel-Information)

![Amsterdam Hotel](https://images.trvl-media.com/lodging/1000000/30000/20800/20793/945f7842_y.jpg)

### Amsterdam Hotel

10/10 Excellent

"Patricio, Rachel and Indina (sp?) made the stay fantastic! clean & comfortable, easily walkable area & a great team! thanks!"

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

![Hyatt Regency Greenwich](https://images.trvl-media.com/lodging/1000000/20000/18200/18180/49323a81_y.jpg)

### Hyatt Regency Greenwich

2/10 Terrible

"Me and my wife stayed in Hyatt Regency Greenwich Old Greenwich, Connecticut for 3 days, it was the most horoble experiance in my life, whaen I open the door of my room I get the roof of the hotel as a view of my window, the room was verry far fron the eleventer, the room service knocking on my door at 9am, I ask for couple plate "

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

![DoubleTree by Hilton Hotel Nanuet](https://images.trvl-media.com/lodging/1000000/10000/800/736/c532560d_y.jpg)

### DoubleTree by Hilton Hotel Nanuet

6/10 Okay

"Clean room, friendly staff, big rooms. The only negative thing is there was people yelling all night, throwing stuff around you can hear everything and the banging. Once the lady left her partner was yelling in the hallway by himself. I couldn’t sleep. The lady came back in the morning and was talking loud which woke me up again "

[](https://expedia.ca/Nyack-Hotels-DoubleTree-By-Hilton-Hotel-Nanuet.h736.Hotel-Information)

![Royal Hotel Bronx](https://images.trvl-media.com/lodging/93000000/92010000/92007800/92007795/w905h1598x0y1-2ad62143_y.jpg)

### Royal Hotel Bronx

2/10 Terrible

"There was roaches in the room, and them room was really small with a horrible smell. "

[](https://expedia.ca/New-York-Hotels-Royal-Hotel-Bronx.h92007795.Hotel-Information)

![Sonesta White Plains Downtown](https://images.trvl-media.com/lodging/1000000/10000/10000/9979/76900125_y.jpg)

### Sonesta White Plains Downtown

10/10 Excellent

"Great staff and clean room."

[](https://expedia.ca/White-Plains-Hotels-Sonesta-White-Plains-Downtown.h9979.Hotel-Information)

![LIV Hotel Bronx - Newly Built](https://images.trvl-media.com/lodging/118000000/117970000/117967600/117967593/ef0e434d_y.jpg)

### LIV Hotel Bronx - Newly Built

10/10 Excellent

"Good "

[](https://expedia.ca/New-York-Hotels-LIV-Hotel-Bronx.h117967593.Hotel-Information)

![Windrose On Hudson](https://images.trvl-media.com/lodging/113000000/112810000/112806700/112806652/d1beb6ce_y.jpg)

### Windrose On Hudson

8/10 Good

"We decided stay at this hotel, because it is only option was. In general all good. Big parking lot, polite staff. But, room doesn't have fridge, and for my request slippers, they said, they don't have it. There are the reasons why I little bit disappointed."

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

## Find out more about Ossining

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Ossining. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Apartments in Ossining ](https://expedia.ca/Ossining-Apartments.d6190653-aaApartments.Travel-Guide-Accommodation)
- [Vacation Homes in Ossining ](https://expedia.ca/Ossining-Private-Vacation-Homes.d6190653-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Ossining ](https://expedia.ca/Ossining-Cottages.d6190653-aaCottages.Travel-Guide-Accommodation)
- [Villas in Ossining ](https://expedia.ca/Ossining-Villas.d6190653-aaVillas.Travel-Guide-Accommodation)
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- [Aparthotels in Ossining ](https://expedia.ca/Ossining-Apart-Hotels.d6190653-aaApartHotels.Travel-Guide-Accommodation)
- [Guest Houses in Ossining ](https://expedia.ca/Ossining-Guest-Houses.d6190653-aaGuestHouses.Travel-Guide-Accommodation)
- [Cabin Rentals in Ossining ](https://expedia.ca/Ossining-Cabins.d6190653-aaCabins.Travel-Guide-Accommodation)
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