Ossining

Travel 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
Windrose On Hudson

Windrose On Hudson

3 out of 5
1 Shady Lane Farm Road Ossining NY
The price is HK$1,291 per night from 24 May to 25 May
HK$1,291
HK$1,438 total
24 May - 25 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! (134 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
Armoni Inn & Suites

Armoni Inn & Suites

3.5 out of 5
329 Route 303 Orangeburg NY
The price is HK$516 per night from 17 May to 18 May
HK$516
HK$575 total
17 May - 18 May
includes taxes & fees
Stay at this business-friendly hotel in Orangeburg. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the clean rooms in their reviews. Popular ...
6/10 (2,204 reviews)
Dirtiest place I have ever stayed at.

Reviewed on 9 May 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
The price is HK$1,120 per night from 12 May to 13 May
HK$1,120
HK$1,281 total
12 May - 13 May
includes taxes & fees
Stay at this business-friendly hotel in Elmsford. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in ...
8.4/10 Very Good! (1,687 reviews)
Keep up the good work!

Reviewed on 10 May 2026

Baymont by Wyndham White Plains - Elmsford
See all 1,350 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 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 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. ...
6.4/10 (114 reviews)
The cleaning is very poor. The bathroom was full of hair and poorly cleaned; the soap, conditioner, and shampoo were on a completely filthy wall, and the air conditioner was filthy. For people who prioritize cleanliness, this hotel is not recommended.

Reviewed on 10 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 family-friendly 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 family-friendly 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