Ossining, NY

Travel Guide

A wooden bridge over a lake with a sign reading "BERGMANN BOARDWALK".
A wooden boardwalk winding through a forest with autumn foliage.
A lake surrounded by autumn-colored trees and houses on a hillside.
A row of historic buildings with distinct architectural styles, including a red brick building with a clock tower and a white building with ornate detailing.
A sunset over a calm lake with several boats anchored.
Windrose On Hudson

Windrose On Hudson

3 out of 5
1 Shady Lane Farm Road Ossining NY
The price is SAR 616 per night from Nov 22 to Nov 23
SAR 616
SAR 687 total
22 Nov - 23 Nov
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 ...
Windrose On Hudson
LIV Hotel Bronx - Newly Built

LIV Hotel Bronx - Newly Built

3 out of 5
3530 Webster Ave Bronx NY
The price is SAR 473 per night from Nov 18 to Nov 19
SAR 473
SAR 555 total
18 Nov - 19 Nov
includes taxes & fees
Stay at this hotel in Bronx. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Yankee Stadium and Bronx Zoo are located nearby.
LIV Hotel Bronx - Newly Built
Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
49 E Sunnyside Lane Tarrytown NY
The price is SAR 704 per night from Dec 6 to Dec 7
SAR 704
SAR 899 total
6 Dec - 7 Dec
includes taxes & fees
Book a stay at this business-friendly hotel in Tarrytown. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant and the helpful ...
Tarrytown House Estate
See all 1,224 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 Sing Sing Prison Museum and Louis Engel Waterfront ...
8.8/10 Excellent! (10 reviews)
"We had a wonderful stay at this property and really enjoyed our time there. The house was very clean, comfortable, and well taken care of, which made us feel right at home. The host was also fantastic—very responsive, easy to communicate with, and always quick to answer any questions we had. Everything ..."

Reviewed on 20 August 2026

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. ...
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 a fitness center. Popular attractions Westchester County ...
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.

Stay near popular Ossining attractions

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.
See properties