The Best Hotels Closest to Pleasant Square in Ossining for 2026

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Our top choices for Pleasant Square hotels

A spacious indoor area with a long row of chairs, a blue sofa, and a wooden table.

A two-story house with a red door, white siding, and a brick pathway leading to the entrance.

A conference room with multiple tables and chairs, a projector, and a presentation screen.

A hotel room with a bed, a desk, a chair, and a view of the outside.

1. Windrose On Hudson

3.1 km from Pleasant Square

Rachel

₩201,135

₩224,015 total

includes taxes & fees

Nov 15 - Nov 16

A spacious living room with a large window, a ceiling fan, a dining area with a table and chairs, and a staircase leading to an upper level.

A swimming pool with lounge chairs and a wooden deck, surrounded by trees and a building with a sloped roof.

A large, two-story house with a prominent front entrance, multiple windows, and a driveway.

A traditional Tudor-style house with a spacious front yard, a stone wall, and a well-maintained garden.

2. Summer Pool Oasis Custom Bar Arcade Pool Table

0.7 km from Pleasant Square

₩646,402

₩1,350,864 total

includes taxes & fees

Nov 3 - Nov 4

A spacious lobby with a modern design, featuring a seating area with sofas and armchairs, a decorative wall panel, and a large window providing natural light.

A hotel lobby with a reception desk, seating area, and a large window allowing natural light.

A hotel room with a large bed, a bedside table with a lamp, a TV, and a bathroom with a mirror and sink.

A modern building with large glass windows, a brick facade, and a curved section.

3. DoubleTree by Hilton Hotel Nanuet

13.8 km from Pleasant Square

Linda

₩179,891

₩209,348 total

includes taxes & fees

Nov 1 - Nov 2

A spacious hotel lobby with a modern design, featuring a large seating area, a dining table, and large windows providing views of the outdoors.

A large indoor swimming pool with clear glass walls, multiple lounge chairs, and ceiling lights.

An outdoor patio with stone walls, a fire pit, and seating.

A modern kitchen with a central island, bar stools, wooden cabinets, and pendant lighting.

4. Element by Marriott Spring Valley

14.8 km from Pleasant Square

Danielle

₩190,340

₩221,509 total

includes taxes & fees

Nov 1 - Nov 2

A modern hotel lobby with a kitchen area, seating arrangements, and large windows offering a view of the outdoors.

A hotel room with a large bed, a desk, and a chair. There is a window with curtains and a wall with a geometric patterned design.

An indoor swimming pool with a glass ceiling, clear signage indicating depth, and lounge chairs along the sides.

A modern hotel lobby with a seating area, a kitchen, and a bar.

5. Baymont by Wyndham White Plains - Elmsford

10.9 km from Pleasant Square

Amanda

₩183,286

₩209,634 total

includes taxes & fees

Nov 1 - Nov 2

A hotel room with a wooden headboard, a bedside table with a lamp, and a bed with white bedding and pillows.

A sign for Ardsley Acres Hotel Court with a landscaped garden in the background.

A motel with a gazebo in the front lawn, a signboard, and several parked cars.

A reception area with a wooden reception desk, a bulletin board with various items, and an exit sign.

6. Ardsley Acres Hotel Westchester

17.1 km from Pleasant Square

David

₩163,213

₩186,693 total

includes taxes & fees

Oct 27 - Oct 28

A hotel with a modern facade, a prominent signage for SpringHill Suites Marriott, and a covered entrance area with seating.

A bar area with a long counter, multiple chairs, and a television mounted on the wall.

A hotel room with a bed, a desk with a chair, a TV, and artwork on the walls.

A modern living room with two orange patterned armchairs, a glass coffee table, a flat-screen TV mounted above a fireplace, and a magazine on the table.

7. SpringHill Suites by Marriott Tarrytown Westchester County

11.2 km from Pleasant Square

Warren

₩207,284

₩237,080 total

includes taxes & fees

Nov 1 - Nov 2

A modern reception area with a wooden reception desk, a blue accent wall, and a large glass door leading to an outdoor seating area.

An indoor swimming pool with a tiled floor, a ceiling with a grid pattern, and a view of greenery outside.

A modern breakfast bar with a variety of food options, including cereal and hot food. There are signs indicating breakfast and hot food availability.

A Holiday Inn Express & Suites hotel with a modern design, featuring a covered entrance and American flags.

8. Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

8.5 km from Pleasant Square

Tammy

₩171,705

₩196,383 total

includes taxes & fees

Nov 15 - Nov 16

A modern lobby with seating areas, a fireplace, and a flat-screen TV mounted on the wall.

A spacious hotel lobby with a modern design, featuring a central seating area with sofas and armchairs, a coffee table, and a television.

A modern bar area with a bar counter, seating, and a colorful mural.

A modern lobby with a reception desk, seating area, and a decorative wall.

9. Cambria Hotel & Suites - White Plains Downtown

16.5 km from Pleasant Square

Christine

₩254,497

₩291,078 total

includes taxes & fees

Nov 15 - Nov 16

A modern kitchen with a large island, bar stools, a flat-screen TV, and a stone backsplash.

A snack and beverage vending area with a refrigerator and shelves stocked with various snacks and drinks.

A lobby with teal patterned chairs, a fireplace, and a flat-screen TV mounted above it.

A hotel room with a bed, a sofa, a nightstand, a lamp, and a framed picture on the wall.

10. Hampton Inn White Plains/Tarrytown

12 km from Pleasant Square

Robin

₩162,628

₩186,005 total

includes taxes & fees

Nov 15 - Nov 16

A modern kitchen with a central island, bar stools, a fireplace, and a contemporary pendant light.

A modern interior with a dark wall, a wooden reception desk, a refrigerator stocked with beverages, shelves with snacks, and a large vase with orange flowers.

A courtyard with a fire pit, outdoor seating, and modern apartment buildings.

A modern cafe with multiple seating options including tables, chairs, and sofas.

11. Courtyard by Marriott Tarrytown Westchester County

10.9 km from Pleasant Square

Syble

₩202,320

₩231,404 total

includes taxes & fees

Nov 1 - Nov 2

A spacious lobby with a red sofa, green armchairs, a fireplace, and a staircase leading to an upper level.

A spacious restaurant with high tables and stools, a bar area, and a television screen displaying a sports game.

A spacious lobby with a red sofa set, a fireplace, and a staircase leading to an upper level.

A hotel entrance with a covered walkway, stone pillars, and potted plants.

12. Hotel MTK Mount Kisco

13.2 km from Pleasant Square

eric w

₩195,372

₩223,457 total

includes taxes & fees

Nov 16 - Nov 17

A hotel patio with outdoor seating, a fire pit, and a covered area with glass doors.

An indoor swimming pool with a 'NO DIVING' sign, lounge chairs, and a lifeguard chair.

A modern living room with a fireplace, a bookshelf, and comfortable seating.

13. Residence Inn Orangeburg

15.4 km from Pleasant Square

KAREN

₩184,927

₩205,965 total

includes taxes & fees

Nov 8 - Nov 9

A spacious lobby with a reception desk, sofas, and a coffee table. There are multiple seating areas and a large window providing natural light.

A modern office space with two monitors, a white desk, black chairs, and a large abstract painting on the wall.

A Sheraton hotel with a modern facade, multiple floors, and a prominent entrance.

A gym with exercise equipment, large windows, and a wooden reception desk.

14. Sheraton Tarrytown Hotel

11.4 km from Pleasant Square

Kerry-Anna

₩190,606

₩218,005 total

includes taxes & fees

Nov 1 - Nov 2

A neatly made bed with a tray of breakfast items including fruits, a glass of orange juice, and a small orchid.

A modern dining area with a wooden table, cushioned seating, pendant lighting, and a large window offering a view of the outdoors.

A modern bar area with a bar counter, multiple stools, and a seating area with a sofa and chairs.

A modern lounge with leather sofas, a patterned rug, and red pendant lights.

15. Hotel Nyack, a JdV by Hyatt Hotel

9.5 km from Pleasant Square

Liana

₩141,091

₩197,431 total

includes taxes & fees

Nov 17 - Nov 18

A modern hotel lobby with a dining area, seating, and a large window offering a view of greenery.

A coffee shop with a wooden interior, a coffee machine, and various snacks and beverages on display.

A balcony with wicker furniture and a white perforated table, overlooking a modern building and a clear sky.

A bar area with teal chairs, a large TV screen, and shelves with bottles and glasses.

16. Hilton Garden Inn Westchester Dobbs Ferry, NY

17.7 km from Pleasant Square

Mustafa

₩179,891

₩205,750 total

includes taxes & fees

Nov 1 - Nov 2

A breakfast area with multiple tables and chairs, a kitchen area with appliances, and a sign for Daybreak Breakfast.

A gym with treadmills, exercise balls, and a yoga mat.

A hotel room with a bed, a desk, and a chair. There are two framed pictures on the wall.

A Days Inn lobby with a stone accent wall, a reception desk, and a sign indicating check-in times.

17. Days Inn by Wyndham Elmsford / White Plains

12.4 km from Pleasant Square

Frankie

₩152,805

₩179,430 total

includes taxes & fees

Nov 2 - Nov 3

A hotel room with a sofa, a coffee table, a TV, a desk, and a bed.

A hotel room with two beds, a desk with a television, and a window with curtains.

A hotel room with a patterned sofa, a small ottoman, a desk with two chairs, a microwave, a wine bottle, and a framed picture on the wall.

A coffee station with two coffee machines and a variety of coffee pods and cups.

18. Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

14.4 km from Pleasant Square

Edwin

₩185,461

₩212,119 total

includes taxes & fees

Nov 15 - Nov 16

A spacious lounge area with comfortable seating, a bar with a well-stocked shelf, and a modern ceiling design.

An outdoor patio area with a fire pit, sofas, and umbrellas.

A spacious dining area with multiple seating options including booths and tables, a kitchen area in the background, and a modern interior design.

A spacious lobby with seating areas, a reception desk, and a large plant.

19. HYATT house White Plains

19.6 km from Pleasant Square

Laura Rebeca

₩236,461

₩270,455 total

includes taxes & fees

Nov 8 - Nov 9

A hotel room with a wooden desk, a green chair, a gray sofa, a kitchenette, and a door with a sign.

A hotel reception area with a wooden floor, a reception desk, and a large window with a view of the parking lot.

A modern hotel lobby with a long communal table, seating area, and a kitchenette.

A Hampton Inn hotel with a clear sky and sunset.

20. Hampton Inn Nanuet

15.1 km from Pleasant Square

Leonard

₩162,628

₩189,258 total

includes taxes & fees

Oct 28 - Oct 29

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Top Pleasant Square Hotel Reviews

ROW NYC

8/10 Good

"Fantastic location. Clean room. I booked one night and extended my stay and the staff member the first night put me in a room with a lower rate, but did not inform me. When I extended my stay, the second staff member offered me a discount based on the room I was in, which was an unexpected happy surprise."

Park Lane New York

10/10 Excellent

"Room was good, great view of the city, and next to central park"

Harmony Suites

8/10 Good

"Although the building didn't feel particularly new, it was well-maintained, and the room was spacious and comfortable. There was a large window facing the area next to the entrance, yet I didn't notice any noise. I had high hopes for breakfast, but it was disappointing to find items like the bacon served cold."

Lotte New York Palace

10/10 Excellent

"I wouldn't stay anywhere else in New York! The location is perfect since I can easily walk to the theater, but don't have to stay in Times Square. (Love the theater; don't love navigating Times Square.) On this trip, special shoutout to Stacy, who greeted me and my daughter so cordially when we arrived late Sunday evening (Oct. 11th) and then the next day helped us with a logistical problem. Can't wait to visit again."

Other attractions near Pleasant Square

Merchants Square

9.0/10 (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 quaint area.

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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.

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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.

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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.

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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.

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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.

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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.

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Louis Engel Waterfront Park

Louis Engel Waterfront Park is just one of the places to see in Ossining, so why not enjoy the other things to explore during your travels? Amble around this quaint area's riverfront and enjoy its top-notch restaurants.

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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 36 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 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 (35.5 km) from Pleasant Square. Other good options around the area include Night Hotel Broadway and Hotel Belleclaire Central Park, a Small Luxury Hotel.

How many hotels can I expect to find near Pleasant Square?

Expedia has 36 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.

Where can I learn more about changing or cancelling my trip in the area near Pleasant Square?

For additional details about updating your stay near Pleasant Square or cancelling it, go to https://www.expedia.com/service/.

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. Van Cortlandt Manor, Sleepy Hollow Cemetery, and Old Dutch Church of Sleepy Hollow are some of the local landmarks to explore. Consider spending a leisurely afternoon outside at Croton Point Park, Rockland Lake State Park, or Louis Engel Waterfront Park.

Find hotels near Pleasant Square, Ossining from ₩179,430

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Our top choices for Pleasant Square hotels

1. Windrose On Hudson

2. Summer Pool Oasis Custom Bar Arcade Pool Table

3. DoubleTree by Hilton Hotel Nanuet

4. Element by Marriott Spring Valley

5. Baymont by Wyndham White Plains - Elmsford

6. Ardsley Acres Hotel Westchester

7. SpringHill Suites by Marriott Tarrytown Westchester County

8. Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

9. Cambria Hotel & Suites - White Plains Downtown

10. Hampton Inn White Plains/Tarrytown

11. Courtyard by Marriott Tarrytown Westchester County

12. Hotel MTK Mount Kisco

13. Residence Inn Orangeburg

14. Sheraton Tarrytown Hotel

15. Hotel Nyack, a JdV by Hyatt Hotel

16. Hilton Garden Inn Westchester Dobbs Ferry, NY

17. Days Inn by Wyndham Elmsford / White Plains

18. Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

19. HYATT house White Plains

20. Hampton Inn Nanuet

Top Pleasant Square Hotel Reviews

ROW NYC

Park Lane New York

Harmony Suites

Lotte New York Palace

Other attractions near Pleasant Square

Merchants Square

Sing Sing Prison Museum

Ossining Public Library

Snowden Avenue Park

Depot Square

Nelson Park

Crawbuckie Park

Louis Engel Waterfront Park

Frequently asked questions