Ossining Holiday Rentals from AU$242: Search Short-Term Rentals

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

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK! : This highly rated holiday home rental in Ossining is located near skiing, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Ossining holiday rentals

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

Ossining

natalie l.

includes taxes & fees

2 Sept - 3 Sept

2. 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

6 Sept - 7 Sept

3. Summer Pool Oasis Custom Bar Arcade Pool Table

Ossining

includes taxes & fees

1 Sept - 2 Sept

4. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

Ossining

includes taxes & fees

20 Sept - 21 Sept

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

Croton-on-Hudson

Mateo A.

includes taxes & fees

17 Sept - 18 Sept

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

Croton-on-Hudson

Ann S.

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

CROTON HDSN

Aimee S.

includes taxes & fees

2 Sept - 3 Sept

8. Luxury NYC Home Game Room Free Parking

White Plains

"After flying in with four of us from Los Angeles on a Red Eye, we had to drive around for 4-5 hours until we were able to check in at 4pm, however after hours of trying to get into the property with no answer on the contact number ,we finally were able to have the local property manager come out and say that the property overbooked and had no room for us. I spent over 2 hours on the phone getting the run around by Expedia with mixed stories of our accommodations. FINALLY with now the story is...

Jorge

includes taxes & fees

31 Aug - 1 Sept

View all properties

Find holiday rentals that suit your style

Apartments

Aparthotels

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Ossining Hotel Reviews

Hotel Nyack, a JdV by Hyatt Hotel

8/10 Good

"Overhead lighting in room very poor. Dark/dim even with all the lights on.room facing Highway noisy. Double not queen beds."

Hampton Inn White Plains/Tarrytown

10/10 Excellent

"The staff very helpful and friendly. Im disappointed the pool wasnt in use again as it has hardly been for many years Ive been going there. I think once in the past ten years Ive seen it open. Remember, Ive been staying at the hampton since 2004. Much has changed in that many years but overall the continental breakfast alone is worth the stay. Its not just a muffin and coffee like most franchises. The diverse menu is very appealing indeed."

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$242 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?

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!: This highly rated holiday home rental in Ossining is located near skiing, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

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 Teatown Lake Reservation and Kitchawan Preserve are a couple of picturesque spots to enjoy the outdoors. Sing Sing Correctional Facility and Ossining Public Library 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.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Ossining holiday rentals

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

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

3. Summer Pool Oasis Custom Bar Arcade Pool Table

4. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

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

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

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

8. Luxury NYC Home Game Room Free Parking

9. Elegant Hideaway with Free Parking

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

11. Piermont Oasis

12. Luxury NYC Home with Free Parking for 12

13. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

14. Prime Luxe 3-BR NYC - Free Parking

15. Harriman Outdoor Center - Mountain Laurel Cabin

16. Family-Friendly 3BR Home • Game Room • Free Parking • Minutes from NYC

17. 2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

18. Walk to WP Gate + Free Parking!

19. Stamford Suites

20. Spacious 3BR Luxe Escape near NYC

Find holiday rentals that suit your style

Top Ossining Hotel Reviews

Hotel Nyack, a JdV by Hyatt Hotel

Hampton Inn White Plains/Tarrytown

Ramada by Wyndham Bronx

Crowne Plaza Suffern - Mahwah by IHG

West Gate Inn Nyack

Windrose On Hudson

Find out more about Ossining

Frequently asked questions

Go further with the Expedia app