
Ossining Vacations from $516
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Your Ossining Vacation
Experience the energy and excitement of Ossining with a tailor-made Ossining vacation package. From its rich history to its spectacular views and beyond, you'll never have a boring moment in this city. Eager to explore your surroundings? Tarrytown Music Hall, Van Cortlandt Manor and Sing Sing Correctional Facility are some of the leading places to visit during a trip to Ossining. Browse Expedia's extensive range of travel options and begin planning your perfect vacation to Ossining now.
The Latest Ossining vacation packages
Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Manhattan Times Square
Manhattan
Save 100% on your flight
Price was $929, price is now $516 per person
$516
per person
Aug 4 - Aug 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,593 reviews)
Check was efficient. I was in line for less than 5 minutes. Online reviews had almost scared me off the hotel with tales of long queues for checking.
Room was small but clean and had everything I needed. In room amenity - soap, platoon etc were of high quality,
I was very pleased with the value I got for the hotel.
Reviewed on Jun 19, 2026

2 bedroom luxury Empire State VIEW
Manhattan
Price was $4,022, price is now $1,514 per person
$1,514
per person
Jul 28 - Jul 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
10/10 Exceptional! (1 review)
Room was very clean and aesthetically pleasing. The views from the property were amazing! Nice and spacious as well. Will book again when I come back to NY!
Reviewed on Mar 19, 2026

Hotel Riu Plaza New York Times Square
Manhattan
Save 100% on your flight
Price was $1,215, price is now $659 per person
$659
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (3,063 reviews)
Good location, big breakfast buffet that was decent, loved happy hour at the bar. The hall way to the room seemed a little dirty or musty to us and the room was pretty decent but the shower drain seemed clogged as it drained slowly and it was kinda awkward taking a shower because the toilet and shower is surrounded by frosted glass and when your showering everyone in the room gets a shadow show of you showering. I guess that’s ok for couples but if you are there with a family or friends then it is different level. lol but all in all we enjoyed it and we would stay again
Reviewed on Jun 17, 2026

Topping Rose House
Price was $6,749, price is now $3,687 per person
$3,687
per person
Sep 2 - Sep 5
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
9/10 Wonderful! (152 reviews)
Overall it was a great stay! Best part of the cottage was the bathroom with its deep big tub and walk in shower.
But the room itself lacked visual appeal & some conveniences usually associated with booking a cottage which is more private and removed from the house. Could use more and better art in the room. I would also trade all the storage space for a mini fridge, tea kettle or coffee maker.
Also the only full-size mirror is hidden far back in the bathroom which isn’t terrible but very inconvenient to check the outfit before heading out the door.
It’s little odd things that just made it not feel like a luxury stay.
And no one mentioned to us beforehand that the sauna, gym, pool area (even though in off season) was under renovation and not available to use.
The restaurant was amazing though, room service was wonderful. And staff were adorable. But I don’t know if we would book again tbh.
Reviewed on Mar 24, 2026

Hotel Beacon
Manhattan
Save 100% on your flight
Price was $1,793, price is now $997 per person
$997
per person
Sep 2 - Sep 7
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9.4/10 Exceptional! (1,496 reviews)
Great location. Staff was great but unfortunately no restaurant or bar like Expedia said.
Reviewed on Jun 18, 2026
Stay near popular Ossining attractions
Ossining Hotel Deals

Windrose On Hudson
1 Shady Lane Farm Road Ossining NY
Fully refundableReserve now, pay when you stay
$206 nightly
The price is $230 total per night from Jun 21 to Jun 22
$230 total
Jun 21 - Jun 22
Total with taxes and fees
8.4/10 Very Good! (170 reviews)
"Well, it’s almost as if on the weekend the hotel doesn’t know it’s a hotel but the rooms are spotless. The property is the most beautiful property I’ve ever seen, but it’s very arbitrary if they want to serve food that day or not or even if the bar is open and signage is just terrible but other than ..."
Reviewed on Jun 15, 2026

Tarrytown House Estate
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
$163 nightly
The price is $186 total per night from Jun 28 to Jun 29
$186 total
Jun 28 - Jun 29
Total with taxes and fees
8.2/10 Very Good! (1,121 reviews)
"This was a magnificent stay! The hotel is perfect!! Amazing location, excellent service! Rooms are comfortable and spacious, I recommend this property for anyone that wants to have an historical and enchanted stay!!!"
Reviewed on Jun 16, 2026

Hyatt Regency Greenwich
1800 E Putnam Avenue Old Greenwich CT
Fully refundableReserve now, pay when you stay
$229 nightly
The price is $263 total per night from Jul 12 to Jul 13
$263 total
Jul 12 - Jul 13
Total with taxes and fees
8.6/10 Excellent! (1,027 reviews)
"Great hotel"
Reviewed on Jun 19, 2026
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.
Find the Best Ossining Vacation Packages
Ossining Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | LaGuardia Airport (LGA) |
Population | 25,400 |
Max Temp Winter | 35ºF |
Max Temp Summer | 80ºF |
Top Sights | Franklin D. Roosevelt State Park, Paramount Hudson Valley Theater and Rockefeller Archive Center |
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- New York Hotels
- Hotels near Sing Sing Prison Museum
- Hotels near Snowden Avenue Park
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- Hotels near Depot Square
- Hotels near Sing Sing Correctional Facility
- Hotels near Nelson Park
- Hotels near Louis Engel Waterfront Park
- Hotels near Ossining Historical Society
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- Hotels near Van Cortlandt Manor
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- Hotels near Croton Point Park
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- Hotels near Hardscrabble Wilderness Area
- Hotels near Rockland Lake State Park Championship Golf Course
- Hotels near Hudson Hills Golf Course
- Croton-On-Hudson Hotels
- B&B in Croton-on-Hudson
- Cabin Rentals in Croton-on-Hudson
- Condo Rentals in Croton-on-Hudson
- Extended Stay America Hotels in Croton-on-Hudson
- 5 Star Hotels in Croton-on-Hudson
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- Motels in Croton-on-Hudson
- Cottages in Croton-on-Hudson
- Vacation Homes in Croton-on-Hudson
- Family Hotels in Croton-on-Hudson
- Apartments in Croton-on-Hudson
- La Quinta Inn & Suites Hotels in Croton-on-Hudson
- 4 Star Hotels in Croton-on-Hudson
- Romantic Hotels in Croton-on-Hudson
- Extended Stay Hotels in Croton-on-Hudson
- Castles in Croton-on-Hudson
- Sing Sing Prison Museum
- Snowden Avenue Park
- Depot Square
- Sing Sing Correctional Facility
- Nelson Park
- Louis Engel Waterfront Park
- Van Cortlandt Manor
- Croton Point Park
- Visit Maryknoll
- Corning Tower
- Visit Briarcliff Manor
- New York Vacations
- Hardscrabble Wilderness Area
- Rockland Lake State Park Championship Golf Course
- Croton Landing Park
- Croton-On-Hudson Vacations
- Rockwood Hall Park
- Teatown Lake Reservation
- Rockland Lake State Park
- Visit Croton-on-Hudson
- Rockland Lake State Park Executive Golf Course
- Car rentals near Ossining Historical Society
- Car rentals near Crotonville
- Car rentals near Briarcliff Manor
- Avis Rental Cars in Briarcliff Manor
- Mini Car Rentals in Briarcliff Manor
- Car rentals near Van Cortlandt Manor
- Car rentals near Croton Point Park
- Car rentals near Hudson Hills Golf Course
- Car rentals near Croton-on-Hudson
- Enterprise Rental Cars in Croton-on-Hudson
- Hertz Rental Cars in Croton-on-Hudson
- Dollar Rent A Car Rental Cars in Croton-on-Hudson
- Alamo Rent A Car Rental Cars in Croton-on-Hudson
- Van Car Rentals in Croton-on-Hudson
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.




















