Title: Pleasant Square Tours - Book Now | Expedia.com [Pleasant Square Hotels](https://expedia.com/Pleasant-Square-Hotels.0-l553248621558034948-0.Travel-Guide-Filter-Hotels)[Flights to Ossining](https://expedia.com/Cheap-Flights-To-Ossining.d6190653.Travel-Guide-Flights)[Car Rentals in Pleasant Square](https://expedia.com/Car-Rentals-In-Pleasant-Square.d553248621558034948.Car-Rental-Guide)[Ossining Vacation Packages](https://expedia.com/Ossining.d6190653.Destination-Travel-Guides) # Pleasant Square Tours ## Visit Pleasant Square Activities [Ossining Travel Guide](https://expedia.com/Ossining.dx6190653) --- --- ## Plan a trip to see Pleasant Square Price found within the past 48 hours. Click for updated prices. ![Hyatt Grand Central New York](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Grand Central New York Manhattan Save 100% on your flight $347 per person Apr 30 - May 3 found 1 day ago Roundtrip flight included Atlanta (ATL) to Newark Liberty Intl. Airport (EWR) 8.2/10 Very Good! (6,333 reviews) Hi, room is good but shower working Reviewed on Feb 20, 2026 ![Hotel Riu Plaza Manhattan Times Square](https://images.trvl-media.com/lodging/61000000/60680000/60677500/60677495/0bd08347_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Manhattan Times Square Manhattan $519 per person Apr 30 - May 3 found 1 day ago Roundtrip flight included Atlanta (ATL) to Newark Liberty Intl. Airport (EWR) 9.2/10 Wonderful! (3,348 reviews) Room and general cleanliness of the entire hotel was great. Staff really are lovely . Great location, rooms are perfect. Breakfast was fantastic and a really great start to the day . Reviewed on Feb 20, 2026 ![Hotel St. James](https://images.trvl-media.com/lodging/2000000/1150000/1144500/1144474/ecd19bcc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel St. James Manhattan $419 per person Apr 30 - May 3 found 1 day ago Roundtrip flight included Atlanta (ATL) to Newark Liberty Intl. Airport (EWR) 8.8/10 Excellent! (6,546 reviews) The room was clean and the bed were comfortable I enjoyed my stay Reviewed on Feb 21, 2026 ### Popular places to visit ![Croton-On-Hudson, New York, USA: Two people on a path, silhouetted under a cloud-filled sky, in Croton Point Park.](https://images.trvl-media.com/place/6093731/ccd26e44-6227-4c45-967c-dce08d5d0f89.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Croton Point Park After visiting Croton Point Park, make a plan to see the other sights and activities in Croton-on-Hudson. Amble around this family-friendly area's riverfront or attend a sporting event. [](https://expedia.com/Croton-Point-Park-Croton-on-Hudson.d6093731.Vacation-Attraction) ![the Great Jack O'Lantern Blaze Sleepy Hollow NY](https://images.trvl-media.com/place/183658/ecedf757-f29a-48fa-b097-854b024c8732.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Van Cortlandt Manor 4.5/5(8 reviews) 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. [](https://expedia.com/Van-Cortlandt-Manor-Croton-on-Hudson.d6207691.Vacation-Attraction) #### Merchants Square 4.5/5(2 reviews) Explore the great outdoors at Merchants Square, a lovely green space in Ossining. Stroll along the riverfront or attend a sporting event in this family-friendly area. [](https://expedia.com/Merchants-Square-Ossining.d553248621558034947.Vacation-Attraction) #### Sing Sing Prison Museum You can spend time browsing the exhibits at Sing Sing Prison Museum during your travels in Ossining. Amble around this quaint area's riverfront and enjoy its top-notch restaurants. [](https://expedia.com/Sing-Sing-Prison-Museum-Ossining.d553248621561873062.Vacation-Attraction) #### 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. [](https://expedia.com/Ossining-Public-Library-Ossining.d950929294549757952.Vacation-Attraction) #### 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 quaint area, or check out its top-notch restaurants. [](https://expedia.com/Snowden-Avenue-Park-Ossining.d553248621558038861.Vacation-Attraction) --- ## Best Lodging Options Near Pleasant Square ## Check availability on hotels close to Pleasant Square [Tonight ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621558034948&startDate=2026-02-22&endDate=2026-02-23)[Feb 22 - Feb 23](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621558034948&startDate=2026-02-22&endDate=2026-02-23) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621558034948&startDate=2026-02-23&endDate=2026-02-24)[Feb 23 - Feb 24](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621558034948&startDate=2026-02-23&endDate=2026-02-24) [Next weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621558034948&startDate=2%2F27%2F2026&endDate=3%2F1%2F2026)[Feb 27 - Mar 1](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621558034948&startDate=2%2F27%2F2026&endDate=3%2F1%2F2026) ![Ly New York Hotel](https://images.trvl-media.com/lodging/102000000/101290000/101289700/101289650/00e8fce3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Ly New York Hotel 15-61 127th St College Point NY [](https://expedia.com/New-York-Hotels-Ly-New-York-Hotel.h101289650.Hotel-Information) ![Hotel Belleclaire](https://images.trvl-media.com/lodging/1000000/210000/201300/201239/b1121e58_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Belleclaire 2175 Broadway New York NY [](https://expedia.com/New-York-Hotels-Hotel-Belleclaire.h201239.Hotel-Information) ![Sheraton New York Times Square Hotel](https://images.trvl-media.com/lodging/1000000/10000/100/87/576ccb20_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sheraton New York Times Square Hotel 811 7th Ave New York NY [](https://expedia.com/New-York-Hotels-Sheraton-New-York-Times-Square-Hotel.h87.Hotel-Information) ![Empire Hotel](https://images.trvl-media.com/lodging/1000000/10000/3700/3670/f27a1835_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Empire Hotel 44 W 63rd St New York NY [](https://expedia.com/New-York-Hotels-Empire-Hotel.h3670.Hotel-Information) ![Lotte New York Palace](https://images.trvl-media.com/lodging/1000000/10000/4900/4818/w1695h1110x0y0-027534be_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Lotte New York Palace 455 Madison Ave New York NY [](https://expedia.com/New-York-Hotels-Lotte-New-York-Palace.h4818.Hotel-Information) ![Park Central Hotel New York](https://images.trvl-media.com/lodging/1000000/10000/4200/4164/777054c0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Park Central Hotel New York 870 7th Ave New York NY [](https://expedia.com/New-York-Hotels-Park-Central-Hotel-New-York.h4164.Hotel-Information) ![Millennium Hotel Broadway Times Square](https://images.trvl-media.com/lodging/1000000/30000/25500/25449/4b967480_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Millennium Hotel Broadway Times Square 145 W 44th St New York NY [](https://expedia.com/New-York-Hotels-Millennium-Hotel-Broadway-Times-Square.h25449.Hotel-Information) ![Hotel Edison Times Square](https://images.trvl-media.com/lodging/1000000/10000/6300/6260/df9c2f28_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Edison Times Square 228 W 47th St New York NY [](https://expedia.com/New-York-Hotels-Hotel-Edison-Times-Square.h6260.Hotel-Information) ![Courtyard by Marriott New York Manhattan / Central Park](https://images.trvl-media.com/lodging/8000000/7020000/7017800/7017732/dc6c76ef_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Courtyard by Marriott New York Manhattan / Central Park 1717 Broadway New York NY [](https://expedia.com/New-York-Hotels-Courtyard-By-Marriott-New-York-Manhattan-Central-Park.h7017732.Hotel-Information) [See all 9,719 properties in Pleasant Square](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=553248621558034948) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=DX_POI_Spring_PROMO_553248621558034948)