Title: Best Hotels Near Pleasant Square, Ossining from CA $142 | Expedia.ca [Vacation Rentals in Ossining](https://expedia.ca/Ossining-Vacation-Rentals.d6190653.Travel-Guide-VacationRentals)[Flights to Ossining](https://expedia.ca/Cheap-Flights-To-Ossining.d6190653.Travel-Guide-Flights)[Pleasant Square Car Rentals](https://expedia.ca/Car-Rentals-In-Pleasant-Square.d553248621558034948.Car-Rental-Guide)[Pleasant Square Vacations](https://expedia.ca/Pleasant-Square-Ossining.d553248621558034948.Vacation-Attraction) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find hotels near Pleasant Square, Ossining from CA $142 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Tonight [Oct 19 - Oct 20](https://www.expedia.ca/Hotel-Search?regionId=553248621558034948&startDate=2025-10-19&endDate=2025-10-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 20 - Oct 21](https://www.expedia.ca/Hotel-Search?regionId=553248621558034948&startDate=2025-10-20&endDate=2025-10-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248621558034948&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248621558034948&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Recommended Price (low to high) Distance Star rating ## Top Hotels Close to Pleasant Square ![Terrace/patio](https://images.trvl-media.com/lodging/113000000/112810000/112806700/112806652/f251141f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/113000000/112810000/112806700/112806652/d1beb6ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/113000000/112810000/112806700/112806652/589f9bbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/113000000/112810000/112806700/112806652/1b1bee23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Windrose On Hudson 3.1 km from Pleasant Square 7.8/10 Good (48) "Beautiful place! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eugene CA $195 CA $217 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Ossining-Hotels-Crotonville-Hotel.h112806652.Hotel-Information) ![House](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/26d1687a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/0c1fd0e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/7ab4378e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/11e211e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Foliage at Westchester Manor - Near Sleepy Hollow 0.7 km from Pleasant Square CA $670 CA $1,411 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Ossining-Hotels-Foliage-At-Westchester-Manor-Near-Sleepy-Hollow.h121520491.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2700/2692/789126d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2700/2692/0065725d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/1000000/10000/2700/2692/ef08228c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/2700/2692/e7a3f9cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Hawthorne Elmsford North by IHG 8.5 km from Pleasant Square 8.8/10 Excellent (905) "Good overnight hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jonathan CA $250 CA $285 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/White-Plains-Hotels-Comfort-Inn-Suites.h2692.Hotel-Information) ![Free daily self-serve breakfast](https://images.trvl-media.com/lodging/1000000/10000/500/438/w8985h6000x10y0-9d556f34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/500/438/7097d010.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/10000/500/438/ae457390.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/10000/500/438/fc526b62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Baymont by Wyndham White Plains - Elmsford 10.9 km from Pleasant Square 8.2/10 Very good (1443) "The rooms and the hospitality was amazing." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Debra CA $200 CA $229 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/White-Plains-Hotels-La-Quinta-Inn-Suites-By-Wyndham-White-Plains-Elmsford.h438.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/580000/573900/573804/048acb1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/580000/573900/573804/6d3ffa61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, 1 Queen Bed, Accessible, Non Smoking | Private kitchen](https://images.trvl-media.com/lodging/1000000/580000/573900/573804/38c97ce7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, 2 Double Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/580000/573900/573804/ce4ae6b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Extended Stay America Suites White Plains Elmsford 12 km from Pleasant Square 6.8/10 (1011) "There was a tiny bit of a smell in the room when I walked in but other than that it was a very nice room and hotel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Helen CA $155 CA $178 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/White-Plains-Hotels-Extended-Stay-America-Suites-White-Plains-Elmsford.h573804.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1460000/1451600/1451596/b741de01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/2000000/1460000/1451600/1451596/dcc4a910.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1460000/1451600/1451596/f68386f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1460000/1451600/1451596/812a793c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn by Wyndham Elmsford / White Plains 12.4 km from Pleasant Square 6.8/10 (1033) "Great staff , clean rooms, good breakfast " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephen CA $142 CA $168 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/White-Plains-Hotels-Days-Inn-By-Wyndham-Elmsford-White-Plains.h1451596.Hotel-Information) ![Interior entrance](https://images.trvl-media.com/lodging/6000000/5850000/5843400/5843352/393dcf26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/6000000/5850000/5843400/5843352/4df6b581.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/6000000/5850000/5843400/5843352/13a478de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/6000000/5850000/5843400/5843352/9bb80187.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### West Gate Inn Nyack 9.6 km from Pleasant Square 7.4/10 Good (1115) "Staff was polite and helpful. Breakfast was delicious. Great stay for visiting conventions or other large events in the area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Francis CA $124 CA $142 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Nyack-Hotels-West-Gate-Inn-Nyack.h5843352.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/1000000/30000/25400/25340/816df1a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served](https://images.trvl-media.com/lodging/1000000/30000/25400/25340/f8aa98ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/25400/25340/7f8b477e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/30000/25400/25340/0945a9bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Tarrytown Westchester County 10.9 km from Pleasant Square 9.0/10 Wonderful (1004) "Staff was very helpful " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) LINDA CA $250 CA $285 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/White-Plains-Hotels-Courtyard-By-Marriott-Tarrytown-Westchester-County.h25340.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/12000000/11950000/11943100/11943081/a38df02c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/12000000/11950000/11943100/11943081/501c20f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/12000000/11950000/11943100/11943081/5c062132.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/12000000/11950000/11943100/11943081/be6358d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Nyack, a JdV by Hyatt Hotel 9.5 km from Pleasant Square 8.6/10 Excellent (1014) "Great location, beautiful rooms and ambiance, incredible food and good service. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Keith CA $144 CA $203 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Nyack-Hotels-Hotel-Nyack.h11943081.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148858/b1419d47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room | View from room](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148858/b5096992.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148858/f8bbba2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148858/a2060364.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn on the Hudson 15.3 km from Pleasant Square 6.8/10 (1004) "The view and the staff were wonderful. The only criticism is that the whole place could use a face lift! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth CA $160 CA $183 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/White-Plains-Hotels-Inn-On-The-Hudson.h1148858.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/800/736/w3839h2556x0y3-9a7a26d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, open 8:30 AM to 9:30 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/800/736/c532560d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/800/736/13a47184.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/800/736/8e33505f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Hotel Nanuet 13.8 km from Pleasant Square 8.8/10 Excellent (1008) "Staff was really friendly" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wanda CA $166 CA $193 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Nyack-Hotels-DoubleTree-By-Hilton-Hotel-Nanuet.h736.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/920000/918700/918639/746d369f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/920000/918700/918639/427525a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, 2 Double Beds](https://images.trvl-media.com/lodging/1000000/920000/918700/918639/17e3241a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, 1 King Bed with Sofa bed | Private spa tub](https://images.trvl-media.com/lodging/1000000/920000/918700/918639/3afe8c48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SpringHill Suites by Marriott Tarrytown Westchester County 11.1 km from Pleasant Square 8.4/10 Very good (1015) "welcoming, efficient front desk staff and beautiful, comfortable room " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathryn CA $225 CA $258 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/White-Plains-Hotels-SpringHill-Suites-By-Marriott-Tarrytown-Westchester-County.h918639.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/460000/459800/459797/2cbe90bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Double Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/460000/459800/459797/9f074a62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/460000/459800/459797/b471bf39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/460000/459800/459797/4f4eaede.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### FairBridge Inn Express Nyack 9.8 km from Pleasant Square 7.6/10 Good (1015) "Very nice hotel and clean and staff are nice" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Sara CA $131 CA $156 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Nyack-Hotels-FairBridge-Inn-Express-Nyack.h459797.Hotel-Information) ![Basic Triple Room | Interior](https://images.trvl-media.com/lodging/12000000/11550000/11546900/11546856/401761e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/12000000/11550000/11546900/11546856/ef671e0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Vending machine](https://images.trvl-media.com/lodging/12000000/11550000/11546900/11546856/34f01a27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/12000000/11550000/11546900/11546856/219f5e19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tappan Zee Hotel 10.4 km from Pleasant Square 6.4/10 (624) "Very pleased " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $157 CA $183 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Nyack-Hotels-Tappan-Zee-Hotel.h11546856.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1420000/1411400/1411304/4da01b6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1420000/1411400/1411304/8f67b3ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1420000/1411400/1411304/5ced7c04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee service](https://images.trvl-media.com/lodging/2000000/1420000/1411400/1411304/da41023c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Motel 6 Elmsford, NY - White Plains 12.2 km from Pleasant Square 6.6/10 (880) "Very affordable compared to surrounding hotels" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) CRAIG A CA $139 CA $159 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/White-Plains-Hotels-Motel-6-Elmsford.h1411304.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/180000/172100/172075/2336337b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free toiletries, towels](https://images.trvl-media.com/lodging/1000000/180000/172100/172075/5ac0a98d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/1000000/180000/172100/172075/421c5d09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/180000/172100/172075/1903c9a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn by Wyndham Nanuet / Spring Valley 15.4 km from Pleasant Square 6.8/10 (1010) "Ample parking" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Desean CA $142 CA $165 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Nyack-Hotels-Days-Inn-By-Wyndham-Nanuet-Spring-Valley.h172075.Hotel-Information) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/30000/23300/23291/d5b0e16e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/30000/23300/23291/cf777994.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/23300/23291/77104878.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/30000/23300/23291/9eba8fe4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn White Plains/Tarrytown 12 km from Pleasant Square 8.0/10 Very good (1230) "Will definitely come visit again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brenda CA $172 CA $197 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/White-Plains-Hotels-Hampton-Inn-White-Plains.h23291.Hotel-Information) ![Free daily self-serve breakfast](https://images.trvl-media.com/lodging/7000000/6550000/6541500/6541495/58071d11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/7000000/6550000/6541500/6541495/150c0508.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/7000000/6550000/6541500/6541495/87e148ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/7000000/6550000/6541500/6541495/5d58f7e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG 14.4 km from Pleasant Square 9.2/10 Wonderful (1008) "Nice hotel at a beautiful location! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph CA $195 CA $223 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/White-Plains-Hotels-Holiday-Inn-Express-Hotel-Suites-Peekskill-Hudson-Valley.h6541495.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/10900/10829/w3995h2667x0y0-3f6e8d0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gift shop](https://images.trvl-media.com/lodging/1000000/20000/10900/10829/e21f7ad0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/10900/10829/1d1fc977.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/1000000/20000/10900/10829/01967267.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Westchester Marriott 11.7 km from Pleasant Square 8.8/10 Excellent (398) "Had a great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brionna CA $289 CA $330 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Tarrytown-Hotels-Westchester-Marriott.h10829.Hotel-Information) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/30000/26800/26788/0d5d6da0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served](https://images.trvl-media.com/lodging/1000000/30000/26800/26788/348f17bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/26800/26788/9a2b47a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/26800/26788/142dd06d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel MTK Mount Kisco 13.2 km from Pleasant Square 8.4/10 Very good (1008) "Great value great staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steve CA $217 CA $249 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/White-Plains-Hotels-Holiday-Inn-Mt-Kisco.h26788.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-02&endDate=2025-11-03®ionId=553248621558034948&adults=2&sort=RECOMMENDED&openPlayBack=true) ## Top Pleasant Square Hotel Reviews ![Paramount Times Square – A Generator Hotel](//images.trvl-media.com/lodging/1000000/30000/24300/24245/0cfe01b2_y.jpg) ### Paramount Times Square – A Generator Hotel 10/10 Excellent "Beautiful but elevator were broken more times than not " [](https://expedia.ca/New-York-Hotels-Paramount-Times-Square.h24245.Hotel-Information) ![Millennium Hotel Broadway Times Square](//images.trvl-media.com/lodging/1000000/30000/25500/25449/4b967480_y.jpg) ### Millennium Hotel Broadway Times Square 10/10 Excellent "Staff" [](https://expedia.ca/New-York-Hotels-Millennium-Hotel-Broadway-Times-Square.h25449.Hotel-Information) ![Sheraton New York Times Square Hotel](//images.trvl-media.com/lodging/1000000/10000/100/87/576ccb20_y.jpg) ### Sheraton New York Times Square Hotel 10/10 Excellent "I have no complaints, we enjoyed our stay!" [](https://expedia.ca/New-York-Hotels-Sheraton-New-York-Times-Square-Hotel.h87.Hotel-Information) ![Hard Rock Hotel New York](//images.trvl-media.com/lodging/75000000/74800000/74799500/74799455/f555e13c_y.jpg) ### Hard Rock Hotel New York 10/10 Excellent "A clean room. On the small side thought for a week stay with very limited clothing storage. Nice terrace area and bar on the ground floor and a good location. " [](https://expedia.ca/New-York-Hotels-Hard-Rock-Hotel-New-York.h74799455.Hotel-Information) ![New York Hilton Midtown](//images.trvl-media.com/lodging/1000000/20000/19800/19768/edb0a1f1_y.jpg) ### New York Hilton Midtown 10/10 Excellent "Museum of Modern art is just a block away. Le Bernadin 3 star Michelin restaurant is a short 4 minute walk." [](https://expedia.ca/New-York-Hotels-New-York-Hilton-Midtown.h19768.Hotel-Information) ![Hotel St. James](//images.trvl-media.com/lodging/2000000/1150000/1144500/1144474/ecd19bcc_y.jpg) ### Hotel St. James 10/10 Excellent "The location was perfect for my trip into the city to see shows. It is an easy walk from Penn Station and central located for Broadway. The staff is always very helpful and friendly. They have a room to hold your bag if you come early. The room was clean and efficiently laid out. I would definitely stay again." [](https://expedia.ca/New-York-Hotels-Hotel-St-James.h1144474.Hotel-Information) ![The Park Hotel at Meadowlands](//images.trvl-media.com/lodging/1000000/10000/3200/3129/656db873_y.jpg) ### The Park Hotel at Meadowlands 10/10 Excellent "Stayed here before when it was a sheraton lovely views staff was quick since there was a line forming to check in did not take long gustavo was quick and pleasant all good " [](https://expedia.ca/Jersey-City-Hotels-Hilton-Meadowlands.h3129.Hotel-Information) ![Hyatt Grand Central New York](//images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_y.jpg) ### Hyatt Grand Central New York 10/10 Excellent "Quiet, good staff" [](https://expedia.ca/New-York-Hotels-Grand-Hyatt-New-York.h23677.Hotel-Information) ![Romer Hell's Kitchen](//images.trvl-media.com/lodging/1000000/20000/17600/17583/43e3457b_y.jpg) ### Romer Hell's Kitchen 10/10 Excellent "If there had been complimentary coffee, either in-room or in the lobby, our stay would have been perfect. " [](https://expedia.ca/New-York-Hotels-Romer-Hells-Kitchen.h17583.Hotel-Information) ## Hotels near other Pleasant Square attractions [](https://www.expedia.ca/Merchants-Square-Hotels.0-l553248621558034947-0.Travel-Guide-Filter-Hotels) ### 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. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621558034947) [](https://www.expedia.ca/Sing-Sing-Prison-Museum-Hotels.0-l553248621561873062-0.Travel-Guide-Filter-Hotels) ### 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. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621561873062) [](https://www.expedia.ca/Ossining-Public-Library-Hotels.0-l950929294549757952-0.Travel-Guide-Filter-Hotels) ### 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. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=950929294549757952) [](https://www.expedia.ca/Snowden-Avenue-Park-Hotels.0-l553248621558038861-0.Travel-Guide-Filter-Hotels) ### 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. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621558038861) [](https://www.expedia.ca/Depot-Square-Hotels.0-l553248621558038859-0.Travel-Guide-Filter-Hotels) ### 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. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621558038859) [](https://www.expedia.ca/Crawbuckie-Park-Hotels.0-l950888068527779840-0.Travel-Guide-Filter-Hotels) ### Crawbuckie Park Explore the great outdoors at Crawbuckie Park, a lovely green space in Ossining. Amble around the area's parks or visit its monuments. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=950888068527779840) [](https://www.expedia.ca/Nelson-Park-Hotels.0-l553248621557931331-0.Travel-Guide-Filter-Hotels) ### Nelson Park Nelson 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. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621557931331) [](https://www.expedia.ca/Sing-Sing-Correctional-Facility-Hotels.0-l553248621558038857-0.Travel-Guide-Filter-Hotels) ### 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. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621558038857) ## Frequently asked questions ### What's the area like around Pleasant Square? > Pleasant Square is located in a family-friendly area of Ossining known for its array of dining options and hiking. You'll find 40 hotels and other accommodations within a few miles for a convenient home base. ### Where is the best place to stay close to Pleasant Square? > [Radio Hotel](https://www.expedia.ca/New-York-Hotels-Radio-Hotel.h73530346.Hotel-Information) is one of the top choices for your stay based on our traveler data, and this hotel offers a restaurant and a 24-hour fitness center. You'll find it 22 mi (35.4 km) from Pleasant Square. Other good options around the area include [Night Hotel Broadway](https://www.expedia.ca/New-York-Hotels-Night-Hotel-Broadway.h129325.Hotel-Information) and [Sheraton New York Times Square Hotel](https://www.expedia.ca/New-York-Hotels-Sheraton-New-York-Times-Square-Hotel.h87.Hotel-Information). ### How many hotels can I expect to find near Pleasant Square? > Expedia has 40 hotels and other accommodations a few miles from Pleasant Square. ### If I need to cancel the hotel reservation for my stay near Pleasant Square, will I receive a refund? > Yes, you'll find most room reservations are fully refundable if you cancel prior to the hotel's cancellation deadline, which is usually within 24-48 hours of your arrival date. If your reservation is non-refundable, you might be able to cancel it and receive a refund within a 24-hour period of booking. Add your dates and click on "Search", then you can filter by "fully refundable" to review top deals close to Pleasant Square. ### What can I see and do near Pleasant Square? > You'll want to browse the exhibits at Sing Sing Prison Museum and Ossining Historical Society. Sing Sing Correctional Facility, Van Cortlandt Manor, and Sleepy Hollow Cemetery are some of the local landmarks to explore. Consider spending a leisurely afternoon outside at Croton Point Park, Rockland Lake State Park, or Depot Square. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - [4 Star Hotels in Briarcliff Manor](https://www.expedia.ca/4Star-Briarcliff-Manor-Hotels.s40-0-d7040.Travel-Guide-Filter-Hotels) - [Hotels near NYC-All Airports](https://www.expedia.ca/All-Airports-Airport-Hotels.0-aNYC-0.Travel-Guide-Filter-Hotels) - [Aparthotels in Briarcliff Manor](https://www.expedia.ca/Briarcliff-Manor-Apart-Hotels.d7040-aaApartHotels.Travel-Guide-Accommodation) - [Condo Rentals in Briarcliff Manor](https://www.expedia.ca/Briarcliff-Manor-Condos.d7040-aaCondos.Travel-Guide-Accommodation) - [Beach Hotel Hotels in Briarcliff Manor](https://www.expedia.ca/Briarcliff-Manor-Hotels-Beach-Hotel.0-0-d7040-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Briarcliff Manor](https://www.expedia.ca/Briarcliff-Manor-Hotels-Cheap-Hotels.0-0-d7040-tCheapHotels.Travel-Guide-Filter-Hotels) - 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[Visit Pleasantville](https://www.expedia.ca/Pleasantville.dx9121) - [Visit Rockland Lake](https://www.expedia.ca/Rockland-Lake.dx553248634999145276) - [Car rental Briarcliff Manor](https://www.expedia.ca/Car-Rentals-In-Briarcliff-Manor.d7040.Car-Rental-Guide) - [Car rental Croton-on-Hudson](https://www.expedia.ca/Car-Rentals-In-Croton-On-Hudson.d183658.Car-Rental-Guide) - [Car rental Pleasantville](https://www.expedia.ca/Car-Rentals-In-Pleasantville.d9121.Car-Rental-Guide) - [Briarcliff Manor Vacation Rentals](https://www.expedia.ca/Briarcliff-Manor-Vacation-Rentals.d7040.Travel-Guide-VacationRentals) - [Croton-On-Hudson Vacation Rentals](https://www.expedia.ca/Croton-On-Hudson-Vacation-Rentals.d183658.Travel-Guide-VacationRentals) - [Things to do in Briarcliff Manor](https://www.expedia.ca/Things-To-Do-In-Briarcliff-Manor.d7040.Travel-Guide-Activities) - [Things to do in Croton-on-Hudson](https://www.expedia.ca/Things-To-Do-In-Croton-On-Hudson.d183658.Travel-Guide-Activities)