Ossining Vacations

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Find the Best Ossining Vacation Packages

Ossining Hotel Deals

Windrose On Hudson

Windrose On Hudson

3 out of 5
1 Shady Lane Farm Road Ossining NY
Fully refundableReserve now, pay when you stay
The price is ₩317,491 per night from Jun 21 to Jun 22
₩317,491
₩353,584 total
Jun 21 - Jun 22
includes taxes & fees
8.6/10 Excellent! (171 reviews)
"It was a very easy stay, even though we were a couple in our own room and this place is geared towards larger groups"

Reviewed on Jun 19, 2026

Windrose On Hudson
Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
The price is ₩201,335 per night from Jun 30 to Jul 1
₩201,335
₩286,408 total
Jun 30 - Jul 1
includes taxes & 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

Tarrytown House Estate
Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
1800 E Putnam Avenue Old Greenwich CT
Fully refundableReserve now, pay when you stay
The price is ₩383,577 per night from Jun 28 to Jun 29
₩383,577
₩441,114 total
Jun 28 - Jun 29
includes taxes & fees
8.6/10 Excellent! (1,028 reviews)
"The room was clean and very spacious. The lit wardrobe was nice and helpful. The courtyard view was nice. The staff was very helpful and courteous. I also liked the indoor pool and hot tub."

Reviewed on Jun 19, 2026

Hyatt Regency Greenwich
See all 1,338 properties in Ossining
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.

Discover the most popular places to visit in Ossining

Thomas J. Watson Research Center

Learn about the local history of Ossining with a stop at Thomas J. Watson Research Center. Stroll along the riverfront in this quaint area, or check out its top-notch restaurants.

Thomas J. Watson Research Center

Kitchawan Preserve

Explore the great outdoors at Kitchawan Preserve, a lovely green space in Ossining. Amble around this quaint area's riverfront and enjoy its top-notch restaurants.

Kitchawan Preserve

Sing Sing Prison Museum

You can spend time browsing the exhibits at Sing Sing Prison Museum during your travels in Ossining. Amble around this quaint area's riverfront and enjoy its top-notch restaurants.

Sing Sing Prison Museum

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.