Ossining, NY

Travel 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 ¥29,360 per night from Sep 6 to Sep 7
¥29,360
¥32,700 total
Sep 6 - Sep 7
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 ...
8.6/10 Excellent! (224 reviews)
"The staff were very nice. The property was very interesting and large and has pretty patio areas and indoor sitting spots. The outdoor areas/trails need more attention, even though there was a fairly clear mowed and wooded path. There was no food available later in the evening, which was a problem ..."

Reviewed on Aug 19, 2026

Windrose On Hudson
Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
49 E Sunnyside Lane Tarrytown NY
The price is ¥25,159 per night from Aug 27 to Aug 28
¥25,159
¥32,732 total
Aug 27 - Aug 28
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
Royal Regency Hotel

Royal Regency Hotel

3.5 out of 5
165 Tuckahoe Rd Yonkers NY
The price is ¥17,495 per night from Sep 7 to Sep 8
¥17,495
¥21,392 total
Sep 7 - Sep 8
includes taxes & fees
Book a stay at this business-friendly hotel in Yonkers. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant ...
8.6/10 Excellent! (2,852 reviews)
"Restaurant food"

Reviewed on Aug 21, 2026

Royal Regency Hotel
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 Ossining Public Library and Sing Sing Prison Museum ...
8.8/10 Excellent! (9 reviews)
"It's an elegant older house with lots of room for company. Family friendly. The pool was great. My family enjoyed it."

Reviewed on Jul 29, 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. ...
6.4/10 (162 reviews)
"Old and out dated. Carpet worn down, torn, and stained. elevator dirty and dusty, paint chipping. kitchen dirty."

Reviewed on Aug 19, 2026

Stamford Suites
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery NY
Stay at this cottage in Fort Montgomery. Enjoy free WiFi, a garden, and patios. Popular attractions Bear Mountain State Park and Manitoga The Russel Wright Design ...
9.8/10 Exceptional! (141 reviews)
"This was perfect for my husband and me. Couldn't get enough of the view of the surrounding mountains, the Hudson, and the bridge. Communication was prompt and helpful. Would love to comeback in the autumn!"

Reviewed on Jul 16, 2026

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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

Cities near Ossining

Explore a world of travel with Expedia