Ossining Holiday Rentals from AU$249: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Ossining has to offer?

Modern Luxury Home w GameRoom & Parking : This holiday home rental outside Ossining is situated near the airport, and has a rooftop terrace and free WiFi to help you feel content during your stay. It has 3 bedrooms, as well as a kitchen with a full-sized fridge, a dishwasher and a stovetop, so that you can cook with friends or family. Another good choice for your trip to Ossining is Castle Retreat w/ Pool, BBQ, Game Room & Pets OK! .

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Our top choices for Ossining holiday rentals

A hallway with hardwood flooring, a staircase, and a dining area with a chair and table.

1. Snow Days & City Escapes: Spacious Ossining Home

Ossining

includes taxes & fees

21 Oct - 22 Oct

A modern kitchen with white cabinets, a stainless steel dishwasher, a black granite countertop, and a window with a view of trees.

2. Snow Days & City Escapes: Spacious Ossining Home

Ossining

Justeen P.

includes taxes & fees

21 Oct - 22 Oct

A covered area with exercise equipment, chairs, and a view through large windows.

3. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

Ossining

includes taxes & fees

8 Nov - 9 Nov

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.

4. Summer Pool Oasis Custom Bar Arcade Pool Table

Ossining

includes taxes & fees

3 Nov - 4 Nov

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

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

Ossining

natalie l.

includes taxes & fees

14 Oct - 15 Oct

6. Polished 1BR w/ Accessible Room Features + Sauna

Ossining

"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. "

Nada S.

includes taxes & fees

8 Nov - 9 Nov

A neatly made bed with a black and white duvet, a wooden headboard, and a bedside table with a lamp. There are three framed artworks on the wall above the bed.

7. 'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

Croton-on-Hudson

Ann S.

includes taxes & fees

1 Nov - 2 Nov

A stone staircase leading to a house with a stone wall and a metal gate.

8. Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

Croton-on-Hudson

Eva C.

includes taxes & fees

15 Oct - 16 Oct

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Top Ossining Hotel Reviews

J House Greenwich

8/10 Good

"THE LOBBY STAFF WAS CORDIAL, THE VALETS WERE VERY ACCOMODATING. THE ROOM WAS NOT AS PRISTINE CLEAN AS OUR FIRST VISIT, AND THE ROOM ACTUALLY HAD A BIT MORE WEAR AND TEAR. THE DRAPES WERE NOT WORKING EASILY AND THE BATHROOM DOOR DID NOT CLOSE ALL THE WAY."

Clinton Inn Hotel & Event Center

10/10 Excellent

"Honestly wasn't sure what to expect since other stays in the NJ state have been hit or miss, but this stay exceeded our expectations. Check in was a breeze, and staff was friendly. The gentleman at the front desk, I believe his name was Suma, was beyond hospitable, gave us some travel info to get into manhattan, and just overall helpful and friendly person. His gestures and kindness just made us decide right then and there that we would stay there everytime we are in the area. One small critique is that the bathrooms could use some updates, however, the bathrooms have a lot of little things that most hotels don't have like q-tips and a ponytail Kit which my girlfriend loved. Free parking, and a big parking lot is also a plus."

Find out more about Ossining

Everything you need to know about Ossining holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Ossining holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Ossining holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Ossining holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Ossining. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Ossining holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Ossining holiday rentals we have selected for you start as low as AU$249 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Ossining rentals

At Expedia, we put the best Ossining holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Ossining rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Ossining holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Ossining. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a holiday rental in Ossining?

Yes, there are holiday rentals in Ossining close to Labyrinth, or you can select a more secluded option if you're looking for a relaxing stay. Ossining is known for its restaurants and parks. Make sure you have time to check out the golf courses and university setting during your trip.

What are some of the best holiday rentals that Ossining has to offer?

Modern Luxury Home w GameRoom & Parking: This holiday home rental outside Ossining is situated near the airport, and has a rooftop terrace and free WiFi to help you feel content during your stay. It has 3 bedrooms, as well as a kitchen with a full-sized fridge, a dishwasher and a stovetop, so that you can cook with friends or family. Another good choice for your trip to Ossining is Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!.

How many holiday rentals will I find in Ossining?

With 8 Expedia holiday rentals, you're guaranteed to find just the right place for your Ossining stay.

What’s there to see and do in Ossining?

Cultural attractions include Sing Sing Prison Museum and Ossining Historical Society, whereas Louis Engel Waterfront Park and Teatown Lake Reservation are a couple of picturesque spots to enjoy the outdoors. Hudson Hills Golf Course and Thomas J. Watson Research Center are other places to visit while you're in town.

What’s a holiday rental in Ossining like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Ossining. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for a family getaway.

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Our top choices for Ossining holiday rentals

1. Snow Days & City Escapes: Spacious Ossining Home

2. Snow Days & City Escapes: Spacious Ossining Home

3. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

4. Summer Pool Oasis Custom Bar Arcade Pool Table

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

6. Polished 1BR w/ Accessible Room Features + Sauna

7. 'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

8. Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

9. Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

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

11. 1 Queen Bed | Non-Smoking

12. Piermont Oasis

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

14. Contemporary Cozy Cottage

15. Cozy 1-bedroom retreat minutes from West Point!

16. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

17. 1 King Bed | Non-Smoking

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

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

20. Luxury Urban Retreat + Spacious & Stylish

Find holiday rentals that suit your style

Top Ossining Hotel Reviews

J House Greenwich

Hyatt Regency Greenwich

Clinton Inn Hotel & Event Center

Baymont by Wyndham White Plains - Elmsford

Windrose On Hudson

West Gate Inn Nyack

Sleepy Hollow Hotel, a Dolce by Wyndham

Hilltop Inn & Suites

Royal Hotel Bronx

Find out more about Ossining

Frequently asked questions

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