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. ![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 Save 100% on your flight $299 per person Apr 21 - Apr 23 found 1 day ago Roundtrip flight included Atlanta (ATL) to Newark Liberty Intl. Airport (EWR) 8.8/10 Excellent! (6,546 reviews) Clean room and ability to store luggage before check in and after check out Reviewed on Feb 18, 2026 ![Sound View Greenport](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sound View Greenport Save 100% on your flight $737 per person Apr 2 - Apr 9 found 3 hours ago Roundtrip flight included Atlanta (ATL) to New York (JFK) 8.6/10 Excellent! (590 reviews) Very simple room . Restaurant didn’t work because 1/1 and the Reviewed on Jan 10, 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 Save 100% on your flight $430 per person Apr 21 - Apr 23 found 1 day ago Roundtrip flight included Atlanta (ATL) to Newark Liberty Intl. Airport (EWR) 9.2/10 Wonderful! (3,348 reviews) Everything about this hotel is fabulous!! Location, SERVICE, ammenities, cleanliness, design and super spacious rooms which is rare in NY at this pricepoint. Reviewed on Feb 18, 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 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 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=2026-02-18&endDate=2026-02-19)[Feb 18 - Feb 19](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621558034948&startDate=2026-02-18&endDate=2026-02-19) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621558034948&startDate=2026-02-19&endDate=2026-02-20)[Feb 19 - Feb 20](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621558034948&startDate=2026-02-19&endDate=2026-02-20) [This weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621558034948&startDate=2%2F20%2F2026&endDate=2%2F22%2F2026)[Feb 20 - Feb 22](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621558034948&startDate=2%2F20%2F2026&endDate=2%2F22%2F2026) [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) ![The Manhattan at Times Square](https://images.trvl-media.com/lodging/1000000/10000/7500/7498/52d0157f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Manhattan at Times Square 790 7th Ave New York NY [](https://expedia.com/New-York-Hotels-The-Manhattan-At-Times-Square-Hotel.h7498.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) [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)