Pleasant Square Tours

Visit Pleasant Square

Activities

Ossining Travel Guide

Plan a trip to see Pleasant Square

Price found within the past 48 hours. Click for updated prices.

INNSiDE by Meliá New York Nomad

Manhattan

Save 100% on your flight

$290

per person

Jan 8 - Jan 11

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

9.2/10 Wonderful! (2,030 reviews)

The staff were super welcoming, it was a large hotel room on the top floor. Would definitely stay here again!

Reviewed on Oct 30, 2025

The Inn At Fox Hollow Hotel

$387

per person

Jan 8 - Jan 12

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

9.2/10 Wonderful! (1,002 reviews)

Stayed in for one night and the room was beautiful. The bed was beyond comfortable and clean. From the check in to check out, staff was very helpful. 100% will recommend.

Reviewed on Oct 25, 2025

The Mansion at Glen Cove

Save 100% on your flight

$355

per person

Jan 22 - Jan 25

found 13 hours ago

Roundtrip flight included

Atlanta (ATL) to New York (NYC)

7/10 Good! (1,001 reviews)

What I did not like, bathroom setup. One hook by the shower, no hooks by the sink for hand towels. No shelf in the shower for any bath products, everything has to be put on the floor of the shower. Shower fixtures not easy to switch, overall experience very dissatisfing.

Reviewed on Oct 26, 2025

Popular places to visit

the Great Jack O'Lantern Blaze Sleepy Hollow NY

Van Cortlandt Manor

You can learn about the history of Croton-on-Hudson with a stop at Van Cortlandt Manor. Amble around this family-friendly area's riverfront or attend a sporting event.

Merchants Square

Explore the great outdoors at Merchants Square, a lovely green space in Ossining. Stroll along the riverfront or attend a sporting event in this quaint area.

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.

Ossining Public Library

Learn about the local history of Ossining when you spend time at Ossining Public Library. Amble around the area's parks or visit its monuments.

Snowden Avenue Park

Snowden Avenue Park is just one of the places to see in Ossining, so why not enjoy the other things to explore during your travels? Stroll along the riverfront in this family-friendly area, or check out its top-notch restaurants.

Depot Square

Explore the great outdoors at Depot Square, a lovely green space in Ossining. Stroll along the riverfront or attend a sporting event in this quaint area.

Best Lodging Options Near Pleasant Square

Check availability on hotels close to Pleasant Square

Radio Hotel

2420 Amsterdam Ave, New York, NY

Night Hotel Broadway

215 W 94th St, New York, NY

Sheraton New York Times Square Hotel

811 7th Ave, New York, NY

Empire Hotel

44 W 63rd St, New York, NY

Hotel Beacon

2130 Broadway at 75th Street, New York, NY

Lotte New York Palace

455 Madison Ave, New York, NY

Hyatt Grand Central New York

109 East 42nd Street, at Grand Central Terminal, New York, NY

Park Central Hotel New York

870 7th Ave, New York, NY

Paramount Times Square – A Generator Hotel

235 West 46th Street, New York, NY

See all 8,643 properties in Pleasant Square

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.