A wooden boardwalk winding through a forest with autumn foliage.

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Ossining holiday rentals

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

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

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Ossining
8.8 out of 10, Excellent, (10 reviews)
"Super fun location! Host was very helpful. The house is very comfortable for large groups "
United States
natalie l.
The price is £749
includes taxes & fees
28 Sept - 29 Sept
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
A covered area with exercise equipment, chairs, and a view through large windows.

2. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

1BR Queen near NYC | Trails, Biking & Sauna Bliss
Ossining
The price is £239
includes taxes & fees
27 Sept - 28 Sept
1BR Queen near NYC | Trails, Biking & Sauna Bliss
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.

3. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is £924
includes taxes & fees
28 Sept - 29 Sept
Summer Pool Oasis Custom Bar Arcade Pool Table
A covered area with exercise equipment, chairs, and a view through large windows.

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

Polished 1BR w/ Accessible Room Features + Sauna
Ossining
6.0 out of 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
Nada S.
The price is £244
includes taxes & fees
27 Sept - 28 Sept
Polished 1BR w/ Accessible Room Features + Sauna
A stone staircase leading to a house with a stone wall and a metal gate.

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

Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
Croton-on-Hudson
9.6 out of 10, Exceptional, (24 reviews)
"A lovely spot, very nice accommodations.Breakfast supples thoughtfully supplied as well as champagne to enjoy. "
United States
Eva C.
The price is £311
includes taxes & fees
7 Oct - 8 Oct
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
A modern living room with a stone fireplace, a leather sofa, a yellow armchair, a flat-screen TV, and a bookshelf.

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

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Croton-on-Hudson
10.0 out of 10, Exceptional, (8 reviews)
"We had an extended stay at Croton Quarters, it was great! The hosts truly are pet-friendly, the location is ideal, and the property comfortable for a longer term visit. "
United States
Mateo A.
The price is £307
includes taxes & fees
30 Sept - 1 Oct
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
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 Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Croton-on-Hudson
10.0 out of 10, Exceptional, (3 reviews)
"Great stay!"
United States
Ann S.
The price is £239
includes taxes & fees
27 Sept - 28 Sept
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
A dining table set with plates, cutlery, and glasses, with a bowl of fruit and a wine glass in the background.

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

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
CROTON HDSN
9.8 out of 10, Exceptional, (93 reviews)
"Our stay was just perfect! We chose the location based on being close-ish to family in northern Westchester and friends in the city and it was perfect. Maria is an excellent host and super attentive and helpful when needed. The apartment was the perfect size for our family and super cozy after a long day. We'd definitely stay again!"
United States
Aimee S.
The price is £284
includes taxes & fees
4 Oct - 5 Oct
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
A parking lot with multiple cars, a building with red awnings, and trees in the background.

9. 2 Full Beds | Non-Smoking

2 Full Beds | Non-Smoking
Elmsford
The price is £111
includes taxes & fees
28 Sept - 29 Sept
2 Full Beds | Non-Smoking
A garden with a stone wall, a wooden fence, and a gravel path.

10. Piermont Oasis

Piermont Oasis
Piermont
9.6 out of 10, Exceptional, (21 reviews)
"Great place to stay! "
United States
Megan D.
The price is £160
includes taxes & fees
15 Oct - 16 Oct
Piermont Oasis
A house with a view of a bridge and mountains.

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

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (146 reviews)
"We had a great stay!!"
United States
Jasmine
The price is £255
includes taxes & fees
29 Sept - 30 Sept
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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.

12. Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
4.0 out of 10, (1 review)
"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...
United States
Jorge
The price is £536
includes taxes & fees
4 Oct - 5 Oct
Luxury NYC Home Game Room Free Parking
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.

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

Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC
White Plains
2.0 out of 10, (1 review)
"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...
United States
James D.
The price is £390
includes taxes & fees
28 Sept - 29 Sept
Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC
A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

14. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (40 reviews)
"Our stay was very nice and described as listed! We recommend anyone who is interested to stay! "
United States
Aj L.
The price is £318
includes taxes & fees
7 Oct - 8 Oct
Contemporary Cozy Cottage
A wooden cabin with large windows, a wooden bench, and a view of the forest.

15. Harriman Outdoor Center - Mountain Laurel Cabin

Harriman Outdoor Center - Mountain Laurel Cabin
Haverstraw
The price is £173
includes taxes & fees
28 Sept - 29 Sept
Harriman Outdoor Center - Mountain Laurel Cabin
A parking lot with multiple cars, a building with red awnings, and trees in the background.

16. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Elmsford
The price is £109
includes taxes & fees
28 Sept - 29 Sept
1 King Bed | Non-Smoking
A parking lot with multiple cars, a building with red awnings, and trees in the background.

17. 1 Queen Bed | Smoking

1 Queen Bed | Smoking
Elmsford
The price is £106
includes taxes & fees
28 Sept - 29 Sept
1 Queen Bed | Smoking
A parking lot with multiple cars, a building with red awnings, and trees in the background.

18. 1 Queen Bed | Non-Smoking

1 Queen Bed | Non-Smoking
Elmsford
The price is £106
includes taxes & fees
28 Sept - 29 Sept
1 Queen Bed | Non-Smoking
A dining table with a variety of pastries and fruits, a vase with flowers, and a view of a brick wall and greenery outside.

19. Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12
4.0 star property
White Plains
2.0 out of 10, (1 review)
"Place didn't exist. Host did not respond to requests to clarify check-in. Upon arriving, the location was not as described and an individual who answered the door informed our party this was not a rental property. Had to last minute book elsewhere."
United States
Kathleen
The price is £472
includes taxes & fees
26 Sept - 27 Sept
Luxury NYC Home with Free Parking for 12
A modern kitchen with stainless steel appliances, a central island with chairs, and a window with a view.

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

Family-Friendly 3BR Home • Game Room • Free Parking • Minutes from NYC
White Plains
The price is £413
includes taxes & fees
27 Sept - 28 Sept
Family-Friendly 3BR Home • Game Room • Free Parking • Minutes from NYC
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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Top Ossining Hotel Reviews

LIV Hotel Bronx - Newly Built

LIV Hotel Bronx - Newly Built

10/10 Excellent
"I Enjoyed my stay...Thanks"
Jeannette 1-night trip
Posted 1 hour ago
LIV Hotel Bronx - Newly Built

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, apart-hotels, 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 favorite 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 depends 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 £137 per night. Entering your travel dates in the search wizard you might find 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. 

Explore a world of travel with Expedia

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 Teatown Lake Reservation and Kitchawan Preserve 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.