Ossining Travel Guide

Tourist Guide

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
Ossining

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Windrose On Hudson

Windrose On Hudson

3 out of 5
1 Shady Lane Farm Road Ossining NY
The price is NZ$308 per night from 10 May to 11 May
NZ$308
10 May - 11 May
includes taxes & fees
Stay at this business-friendly hotel in Ossining. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Popular attractions Van Cortlandt Manor and Croton ...
8.4/10 Very Good! (133 reviews)
Phone in room did not work. One extra pillow granted would have liked still another. Beautiful facility and grounds very very tasteful throughout.

Reviewed on 1 May 2026

Windrose On Hudson
Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
49 E Sunnyside Lane Tarrytown NY
The price is NZ$301 per night from 10 May to 11 May
NZ$301
10 May - 11 May
includes taxes & fees
Stay at this business-friendly hotel in Tarrytown. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the restaurant and the helpful staff ...
8.2/10 Very Good! (1,066 reviews)
Access to our room was difficult. There was a paved path from the parking lot to exterior wooden steps up to the outside door. It took several tries to get the keycard reader to work. Once inside, there was another flight of stairs to get to our floor. When we got to our room, the card key did not ...

Reviewed on 7 May 2026

Tarrytown House Estate
Sonesta White Plains Downtown

Sonesta White Plains Downtown

4 out of 5
66 Hale Ave White Plains NY
The price is NZ$357 per night from 10 May to 11 May
NZ$357
10 May - 11 May
includes taxes & fees
Stay at this business-friendly hotel in White Plains. Enjoy free Wi-Fi, breakfast (surcharge) and free airport pick-up. Our guests praise the bar and the helpful ...
8.8/10 Excellent! (1,315 reviews)
Lobby restaurant was great

Reviewed on 8 May 2026

Sonesta White Plains Downtown
See all 1,347 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 holiday home in Ossining. Enjoy free Wi-Fi, private pools and a garden. Popular attractions Sing Sing Prison Museum and Croton Point Park 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 Dec 2025

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

Stamford Suites

4 out of 5
720 Bedford St Stamford CT
Stay at this business-friendly aparthotel in Stamford. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. ...
6.6/10 (113 reviews)
Overall average facility

Reviewed on 3 May 2026

Stamford Suites
Global Luxury Suites White Plains

Global Luxury Suites White Plains

3.5 out of 5
57 Bank St White Plains NY
Stay at this business-friendly apartment in White Plains. Enjoy free Wi-Fi, an outdoor pool and valet parking (surcharge). Popular attractions Westchester County ...
6.8/10 (43 reviews)
First day i got there the only one lady at the “front desk”completely ignore me by pretending she didn’t work there, unfortunately for her I stayed at the lobby longer that she had anticipated and had no option but to move behind the desk and ask me “if I needed help” I found that very disrespectful, ...

Reviewed on 19 Apr 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

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
Teatown Lake Reservation

Teatown Lake Reservation

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

Teatown Lake Reservation

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 family-friendly area's riverfront and enjoy its top-notch restaurants.

Sing Sing Correctional Facility

Thomas J. Watson Research Center

Learn about the local history of Ossining when you take a trip to Thomas J. Watson Research Center. Stroll along the riverfront in this quaint area or visit 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

Ossining Public Library

Learn about the local history of Ossining when you take a trip to Ossining Public Library. Amble around the area's parks or visit its monuments.

Ossining Public Library

Cities near Ossining

Mount Kisco Train Station, Westchester, New York, snow,

Mount Kisco

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