Ossining Travel Guide

Tourist Guide

A wooden boardwalk winding through a forest with autumn foliage.
A lake surrounded by autumn-colored trees and houses on a hillside.
A wooden bridge over a lake with a sign reading "BERGMANN BOARDWALK".
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 NZ$360 per night from 23 Aug to 24 Aug
NZ$360
23 Aug - 24 Aug
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 ...
8.6/10 Excellent! (213 reviews)
"NY wedding trip stay: We arrived to check in only to be given a room that had not been turned-clean, called front desk she did apologized and walked the long way back to A202 to hand over our key. This hotel is so old in need for a make over wasn’t expecting this at all! Not having room service nowadays ..."

Reviewed on 6 Aug 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$390 per night from 31 Aug to 1 Sept
NZ$390
31 Aug - 1 Sept
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! (1,223 reviews)
"Expedia listed this as having an adult only outdoor pool. This was not only incorrect but a child had an ‘accident’ in the pool on our second day there which caused the pool to be shut down for the day. The adult pool was the only reason we booked this place. The room smelled so musty that we had ..."

Reviewed on 7 Aug 2026

Tarrytown House Estate
Royal Regency Hotel

Royal Regency Hotel

3.5 out of 5
165 Tuckahoe Rd Yonkers NY
The price is NZ$233 per night from 30 Aug to 31 Aug
NZ$233
30 Aug - 31 Aug
includes taxes & fees
Stay at this business-friendly hotel in Yonkers. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the restaurant in their ...
8.6/10 Excellent! (2,806 reviews)
"Peaceful and calm environment , very friendly"

Reviewed on 7 Aug 2026

Royal Regency Hotel
See all 1,304 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 Ossining Public Library and Louis Engel Waterfront Park ...
8.6/10 Excellent! (8 reviews)
"Technically the house was"clean" but it's grimy. The doors and floors all needed a deep clean. One of the showers had a curtain with red mold stains. The AC could not cool the upstairs properly, and the 3rd floor was excessively hot. The wall to wall carpet on the second floor was smelly. The living ..."

Reviewed on 10 July 2026

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. ...
6.2/10 (152 reviews)
"The front desk gentleman that checked us in was excellent!!"

Reviewed on 1 Aug 2026

Stamford Suites
Uscale 2BR Escape in the Heart of NYC

Uscale 2BR Escape in the Heart of NYC

2 out of 5
280 Jessamine Ave Yonkers NY
Stay at this apartment in Yonkers. Enjoy free Wi-Fi and free parking. Popular attractions Westchester's Ridge Hill and Legoland Discovery Center Westchester ...
8/10 Very good! (1 review)
"The house was very clean and the areas was quiet too. We had a nice spot to park the car. The staff was calling and checking on me if I didn’t have any issues with the check in. They were available all the time. The only thing we will need next time if possible is the washer and dryer and extra towels ..."

Reviewed on 21 Feb 2026

Uscale 2BR Escape in the Heart of NYC
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

A dam with a reservoir, surrounded by autumn foliage and hills.

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

Cities near Ossining

A train station with tracks, a platform, and trees with autumn leaves.

Mount Kisco

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