Ossining, NY

Travel Guide

Boardwalk over marshland on the trail at Teatown Lake Reservation in Ossining, New York.
Boardwalk over marshland on the trail at Teatown Lake Reservation in Ossining, New York.
Westchester, NY, USA: A rail bridge spans an inlet on the Hudson River, with St. Augustine’s Roman Catholic Church, Ossining, NY, in the background.
The start of the Bergmann boardwalk at Teatown Reservation in Westchester County, New York
rows of Victorian building sit t side by side in downtown Ossining, New York

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Windrose On Hudson

Windrose On Hudson

3 out of 5
1 Shady Lane Farm Road Ossining NY
The price is AED 692 per night from Mar 12 to Mar 13
AED 692
AED 770 total
12 Mar - 13 Mar
includes taxes & fees
Book a stay at this business-friendly hotel in Ossining. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Van Cortlandt Manor and ...
8.4/10 Very Good! (117 reviews)
Amazing staff, from front desk Nelson to the cleaning crew, everyone was amazing! Nice facilities, awesome gym, loved our stay

Reviewed on 27 February 2026

Windrose On Hudson
Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

2.5 out of 5
540 Saw Mill River Rd Elmsford NY
The price is AED 481 per night from Mar 22 to Mar 23
AED 481
AED 550 total
22 Mar - 23 Mar
includes taxes & fees
Book a stay at this business-friendly hotel in Elmsford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.2/10 Very Good! (1,607 reviews)
Dirty

Reviewed on 11 March 2026

Baymont by Wyndham White Plains - Elmsford
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

4 out of 5
425 E Route 59 Nanuet NY
The price is AED 392 per night from Mar 29 to Mar 30
AED 392
AED 456 total
29 Mar - 30 Mar
includes taxes & fees
Book a stay at this golf hotel in Nanuet. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. ...
9/10 Wonderful! (1,081 reviews)
Very friendly staff. Quick and easy check in. Clean room.

Reviewed on 9 March 2026

DoubleTree by Hilton Hotel Nanuet
See all 1,326 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.
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

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

Ossining NY
Stay at this vacation home in Ossining. Enjoy free WiFi, private pools, and a garden. Popular attractions Nelson Park and Sing Sing Prison Museum are located ...
9.2/10 Wonderful! (7 reviews)
Super fun location! Host was very helpful. The house is very comfortable for large groups

Reviewed on 1 December 2025

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Stamford Suites

Stamford Suites

4 out of 5
720 Bedford St Stamford CT
Book a stay at this business-friendly aparthotel in Stamford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
6.4/10 (102 reviews)
This is an older hotel the rooms really need a make over Dirty floors outdated electrical (not up to code)

Reviewed on 17 February 2026

Stamford Suites
Global Luxury Suites White Plains

Global Luxury Suites White Plains

3.5 out of 5
57 Bank St White Plains NY
Book a stay at this business-friendly apartment in White Plains. Enjoy free WiFi, an outdoor pool, and valet parking (surcharge). Popular attractions Westchester ...
7/10 Good! (39 reviews)
The room was so clean and the view was amazing! Check in was also super easy.

Reviewed on 10 February 2026

Global Luxury Suites White Plains
See all 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.

Popular places to visit

Lovely spot in Westchester, NY

Teatown Lake Reservation

Explore the great outdoors at Teatown Lake Reservation, a lovely green space in Ossining. Amble around this family-friendly area's riverfront and enjoy its top-notch restaurants.

Teatown Lake Reservation
Rest stop area beside interstate highway where travelers rest and sight see Tioga Reservoir and Dam in Pennsylvania New York state border

Travelers Rest

After visiting Travelers Rest, make a plan to see the other sights and activities in Ossining. Amble around the area's parks or visit its monuments.

Travelers Rest

Sing Sing Correctional Facility

After visiting Sing Sing Correctional Facility, make a plan to see the other sights and activities in Ossining. Amble around this quaint area's riverfront and enjoy its top-notch restaurants.

Sing Sing Correctional Facility

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

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

Nelson Park

Nelson Park is just one of the places to see in Ossining, so why not enjoy the other things to explore during your travels? Stroll along the riverfront in this family-friendly area, or check out its top-notch restaurants.

Nelson Park