Ossining, NY

Travel Guide

Photo by Linda Zanetti
Photo by Linda Zanetti
Photo by louann ohora
Photo by louann ohora
Photo by regina palmieri
Photo by regina palmieri
Photo by louann ohora
Photo by louann ohora
Photo by Linda Zanetti
Photo by Linda Zanetti
Windrose On Hudson

Windrose On Hudson

3 out of 5
1 Shady Lane Farm Road, Ossining, NY
The price is AED 790 per night from Oct 16 to Oct 17
AED 790
AED 880 total
16 Oct - 17 Oct
includes taxes & fees
Stay at this 3-star hotel in Ossining. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Van Cortlandt Manor and Croton Point Park ...
8.4/10 Very Good! (17 reviews)
"The staff is so pleasant! Loved everything"

Reviewed on 17 September 2025

Windrose On Hudson
Armoni Inn & Suites

Armoni Inn & Suites

3.5 out of 5
329 Route 303, Orangeburg, NY
Stay at this 3.5-star business-friendly hotel in Orangeburg. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the clean rooms and the overall ...
6/10 (2,009 reviews)
"On"

Reviewed on 18 September 2025

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Armoni Inn & Suites
Royal Regency Hotel

Royal Regency Hotel

3.5 out of 5
165 Tuckahoe Rd, Yonkers, NY
The price is AED 391 per night from Sep 28 to Sep 29
AED 391
AED 479 total
28 Sep - 29 Sep
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 ...
8.2/10 Very Good! (2,274 reviews)
Awesome place
"It is always a good experience staying here. Been here a few times. It is quiet, nice and clean and the staff are great"

Reviewed on 17 September 2025

Royal Regency Hotel
See all 1,205 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
Book a stay at this family-friendly vacation home in Ossining. Enjoy free WiFi, private pools, and a water park. Popular attractions Sing Sing Prison Museum ...
8.6/10 Excellent! (4 reviews)
Spacious, good for groups, not very clean
"The photos definitely misrepresent the quality of the property. The house is very dirty (lots of stains) and a little on the creepier side. However, if you have a good group of friends who can have fun anywhere, you’ll enjoy the rental."

Reviewed on 12 January 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 4-star business-friendly aparthotel in Stamford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
5.6/10 (54 reviews)
"Excellent sleep"

Reviewed on 17 August 2025

Stamford Suites
3BR Prime Luxury near NYC w Arcade Room

3BR Prime Luxury near NYC w Arcade Room

2 out of 5
50 Vernon Pl, Yonkers, NY
Stay at this vacation home in Yonkers. Enjoy free WiFi, dry cleaning or laundry services, and in-room washers/dryers. Popular attractions Bronx Zoo and Yonkers ...
8/10 Very Good! (1 review)
Not the entire property
"We thought we rented the entire property, but was half of it. expect a lot of stairs. No bath tubs but two showers. some door knobs and locks need maintenance, but overall nice clean rooms."

Reviewed on 18 August 2025

3BR Prime Luxury near NYC w Arcade Room
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

Lovely spot in Westchester, NY

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 with a stop at Thomas J. Watson Research Center. Stroll along the riverfront in this family-friendly area, or check out its top-notch restaurants.

Thomas J. Watson Research Center

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

Sing Sing Prison Museum

You can spend time browsing the exhibits at Sing Sing Prison Museum during your travels in Ossining. Amble around this family-friendly area's riverfront and enjoy its top-notch restaurants.

Sing Sing Prison Museum

Hudson Hills Golf Course

Enjoy a round of golf in Ossining at Hudson Hills Golf Course. Amble around this family-friendly area's riverfront and enjoy its top-notch restaurants.

Hudson Hills Golf Course