Ossining Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ₩347,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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 ₩243,406 per night from May 24 to May 25
₩243,406
₩271,115 total
May 24 - May 25
includes taxes & fees
8.4/10 Very Good! (129 reviews)
Room was spacious and clean but no refrigerator or microwave. Parking lot a bit of walking distance to front entry. Grab and go a very nice touch with delicious coffee. Toilet overflowed in bathroom and maintenance was right on it. Wanting a tranquil stay… it’s the place to be.

Reviewed on Apr 25, 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 ₩118,248 per night from Apr 27 to Apr 28
₩118,248
₩131,682 total
Apr 27 - Apr 28
includes taxes & fees
6/10 (2,194 reviews)
No towels at bathrooms

Reviewed on Apr 24, 2026

Armoni Inn & Suites
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 ₩224,613 per night from Apr 27 to Apr 28
₩224,613
₩293,806 total
Apr 27 - Apr 28
includes taxes & fees
8.2/10 Very Good! (1,042 reviews)
Great hotel, perfect location. Loved everything about it, front desk staff was wonderful.

Reviewed on Apr 25, 2026

Tarrytown House Estate
See all 1,342 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 family-friendly area, or check out its top-notch restaurants.

Thomas J. Watson Research Center

Sing Sing Prison Museum

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

Sing Sing Prison Museum

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

Explore a world of travel with Expedia

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