Ossining Holiday Houses | Expedia.co.nz

A wooden boardwalk winding through a forest with autumn foliage.

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Our top choices for Ossining holiday homes

A spacious living room with a large window, a ceiling fan, a dining area with a table and chairs, and a staircase leading to an upper level.

1. Summer Pool Oasis Custom Bar Arcade Pool Table

Ossining

includes taxes & fees

1 Sept - 2 Sept

An outdoor dining area with tables set for a formal event, featuring candles, glassware, and floral centerpieces.

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

Ossining

natalie l.

includes taxes & fees

1 Sept - 2 Sept

A room with two beds, white curtains, a ceiling light, and a window with a view.

3. Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups

White Plains

includes taxes & fees

23 Aug - 24 Aug

A bedroom with a large bed, a black sofa, a mirror, and a chandelier.

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

Southeast Yonkers

Jordan S.

includes taxes & fees

24 Aug - 25 Aug

A wooden cabin with large windows, a wooden bench, and a view of the forest.

5. Harriman Outdoor Center - Cranberry Cabin

Haverstraw

includes taxes & fees

31 Aug - 1 Sept

A campfire with a wooden table and benches by a lake.

6. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Greenwich

Martina F.

includes taxes & fees

20 Sept - 21 Sept

An outdoor patio with a fire pit, green chairs, and a table.

7. Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

New Rochelle

Katie M.

includes taxes & fees

23 Aug - 24 Aug

A wooden deck with a table and chairs, overlooking a lake with cherry blossoms and autumn foliage.

8. Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms

Lake Peekskill

includes taxes & fees

15 Sept - 16 Sept

A house with a white front door, a small porch with a white railing, and a window with a green curtain.

9. Fabulous 3bdrm Home w/parking!

Highland Falls

Beth M.

includes taxes & fees

24 Aug - 25 Aug

A modern living room with a glass coffee table, teal sofa, and a television displaying a colorful scene.

10. Luxury 3 BR Near NYC with Easy Parking

Bryn Mawr

includes taxes & fees

23 Aug - 24 Aug

A room with a wooden floor, a white door with a number, and a window with blinds.

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

Highland Falls

Briana T.

includes taxes & fees

24 Aug - 25 Aug

A round outdoor seating area with a teal cushion and patterned pillows, surrounded by greenery and a bamboo wall with string lights.

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

Waterside

Sara C.

includes taxes & fees

20 Sept - 21 Sept

A modern interior with a staircase, white walls, a kitchen area, and a seating area with a sofa and a round table.

13. Stylish 3BR Home with Balcony • Free Parking • Convenient NYC Access

Southeast Yonkers

includes taxes & fees

23 Aug - 24 Aug

A modern living room with a sectional sofa, a glass coffee table, and a marble rug. There are two wall art pieces and a potted plant.

14. Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC

White Plains

"An hour before check-in we were called by the property manager, after four days of messaging them through the app without response, to advise us that the property had an alleged water pipe burst and was unavailable, then attempted to upcharge us for alternate accommodations. An alternate place to stay was finally provided at no additional charge but much smaller than what had been booked. Given the absence of communication for four days and then a sudden incident the day of check-in - the day...

James D.

includes taxes & fees

22 Aug - 23 Aug

A deck with Adirondack chairs, a fire pit, and a grill.

15. 3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

Cornwall

Elisabeth

includes taxes & fees

9 Sept - 10 Sept

A modern kitchen with a large island, white cabinetry, stainless steel appliances, and a view through large windows.

16. Private Country Getaway

Bedford Hills

Karin R.

includes taxes & fees

27 Aug - 28 Aug

A modern living room with a white sofa, a glass coffee table, and a marble-patterned rug.

17. Modern Luxury Home w GameRoom & Parking

Southeast Yonkers

"The property that I paid for 1st, they told me that the pipe busted after I paid the cleaning fee. I paid for a property to sleep 6 people so 1 person had to sleep on the floor & another person had to sleep on a broken futon couch. The bed I was sleeping on was broken & there was pee stains on sheet & blanket. I asked them for a discount because of the unexpected things my family went through & they stopped communicating with me until the next day. But do not get any property rental from these...

Ronnie

includes taxes & fees

24 Aug - 25 Aug

A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

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

Carmel Hamlet

Robert T.

includes taxes & fees

24 Aug - 25 Aug

A modern living room with a white sofa, a glass coffee table, and a kitchen in the background.

19. Cozy 4BR Home • Free Street Parking • Quick NYC Access • Perfect for Families

Southeast Yonkers

"The property was not as advertised in listing. There was only one bathroom instead of two. No washing machine and dryer, this is an housing apartment located on the 3rd floor having to walk up two flights of step with approximately 12/15 steps each flight inside the complex. Not to mention you have to walk up steps to get to the complex. I reached the host once when I entered the apartment to speak of my issues, she stated she would call back in 5 minute I haven’t spoken to her since. The...

Sara K.

includes taxes & fees

23 Aug - 24 Aug

A wooden staircase with a chandelier, leading to an upper floor. A stone wall and a flower arrangement are visible on the left.

20. 6 BR, 4 BA Mansion Close to the City

Getty Square

Megan T.

includes taxes & fees

23 Aug - 24 Aug

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Top Ossining Hotel Reviews

Ethan Allen Hotel

10/10 Excellent

"We’ve stayed in many Connecticut hotels, and this is the cleanest of them all. Ethan Allen clearly takes pride in their brand, and this hotel proves it."

Windrose On Hudson

8/10 Good

"The staff were very nice. The property was very interesting and large and has pretty patio areas and indoor sitting spots. The outdoor areas/trails need more attention, even though there was a fairly clear mowed and wooded path. There was no food available later in the evening, which was a problem when arriving around 9 PM, although they were allowing delivery services. They should at least have snacks for purchase at the front desk. When we found someone else’s takeout container under the bed when we were leaving/checking the room, the front desk gave us a free treat coupon for the nice breakfast spot on the property. They are trying very hard to get this place restarted, and I would go there again."

Find out more about Ossining

Ossining Holiday Homes information

Number of reviews	167
Accommodation	276 Holiday Homes
Lowest Price	NZ$227
Highest Price	NZ$2,273

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Ossining holiday homes

1. Summer Pool Oasis Custom Bar Arcade Pool Table

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

3. Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups

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

5. Harriman Outdoor Center - Cranberry Cabin

6. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

7. Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle