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 ₩315,473 per night from Jun 29 to Jun 30
₩315,473
₩351,337 total
Jun 29 - Jun 30
includes taxes & fees
8.6/10 Excellent! (172 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
Armoni Inn & Suites

Armoni Inn & Suites

3.5 out of 5
329 Route 303 Orangeburg NY
Fully refundableReserve now, pay when you stay
The price is ₩107,622 per night from Jun 24 to Jun 25
₩107,622
₩119,852 total
Jun 24 - Jun 25
includes taxes & fees
6/10 (2,267 reviews)
"Few amenities but adequate WiFi. Good AC, ants, adequate hot water, near restaurants and shopping. No phones in the room, no laundry room, no pool access, parking was plentiful."

Reviewed on Jun 22, 2026

Armoni Inn & Suites
Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

2.5 out of 5
540 Saw Mill River Rd Elmsford NY
Fully refundableReserve now, pay when you stay
The price is ₩219,925 per night from Jun 28 to Jun 29
₩219,925
₩251,539 total
Jun 28 - Jun 29
includes taxes & fees
8.4/10 Very Good! (1,725 reviews)
"👍"

Reviewed on Jun 22, 2026

Baymont by Wyndham White Plains - Elmsford
See all 1,339 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.