Ossining

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 €198 per night from 5 Nov to 6 Nov
€198
5 Nov - 6 Nov
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! (34 reviews)
"We were there two nights. Primary purpose was to have a private family meeting. Doug Stone recommended Cafe 56. We conducted our meeting there at 3 pm after it closed. It was the perfect setting - comfortable, lots of light and private. We enjoyed our stay there and will recommend to others. Only ..."

Reviewed on 8 Oct 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 ...
5.8/10 (2,072 reviews)
"We had an overnight stay; for this purpose, it was perfect."

Reviewed on 7 Oct 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 €137 per night from 26 Oct to 27 Oct
€137
26 Oct - 27 Oct
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! (2,303 reviews)
"I thought everything was great but in the evening it was so loud noisy and loud I thought it was supposed to be from like 10:00 p.m. till like 8:00 a.m. is supposed to be quiet but I don't know what was going on on the second floor but it was crazy yelling and screaming and I couldn't sleep at all ..."

Reviewed on 8 Oct 2025

Royal Regency Hotel
See all 1,238 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 ...
8.8/10 Excellent! (5 reviews)
"Communication was excellent. The house itself is older and fine for its age, but"

Reviewed on 20 Sept 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 (64 reviews)
"Suite, enough space"

Reviewed on 2 Oct 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 Aug 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

Teatown Lake Reservation

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 quaint 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

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 studying the exhibits at Sing Sing Prison Museum 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 quaint area's riverfront and enjoy its top-notch restaurants.

Hudson Hills Golf Course