The Best Hotels Closest to Pleasant Square in Ossining - 2026 Updated Prices

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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 gym with treadmills, a red carpet, and exercise equipment.

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

1. Windrose On Hudson

3.1 km from Pleasant Square

Rachel

₹14,344

₹15,976 total

includes taxes & fees

8 Nov - 9 Nov

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 modern living room with a sectional sofa, a coffee table, and large windows offering a view of trees.

2. Summer Pool Oasis Custom Bar Arcade Pool Table

0.7 km from Pleasant Square

₹46,099

₹96,339 total

includes taxes & fees

3 Nov - 4 Nov

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 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.

A modern restaurant interior with a bar area, seating, and a dessert display.

3. DoubleTree by Hilton Hotel Nanuet

13.8 km from Pleasant Square

Linda

₹12,829

₹14,930 total

includes taxes & fees

1 Nov - 2 Nov

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

A hotel corridor with a patterned carpet, a railing, and a reception desk with a glass partition.

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

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

4. Baymont by Wyndham White Plains - Elmsford

10.9 km from Pleasant Square

Amanda

₹13,071

₹14,950 total

includes taxes & fees

1 Nov - 2 Nov

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

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

5. Element by Marriott Spring Valley

14.8 km from Pleasant Square

Danielle

₹13,574

₹15,797 total

includes taxes & fees

26 Oct - 27 Oct

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

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

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

A café with a counter, coffee machines, a microwave, and a trash can.

6. Ardsley Acres Hotel Westchester

17.1 km from Pleasant Square

David

₹11,640

₹13,314 total

includes taxes & fees

26 Oct - 27 Oct

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

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.

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

7. SpringHill Suites by Marriott Tarrytown Westchester County

11.2 km from Pleasant Square

Warren

₹14,783

₹16,908 total

includes taxes & fees

12 Nov - 13 Nov

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

A modern hotel lobby with a large sofa, dining area, and large windows offering city views.

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

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

8. Cambria Hotel & Suites - White Plains Downtown

16.5 km from Pleasant Square

Christine

₹18,150

₹20,759 total

includes taxes & fees

15 Nov - 16 Nov

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

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

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

8.5 km from Pleasant Square

Tammy

₹13,100

₹14,983 total

includes taxes & fees

15 Nov - 16 Nov

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

A gym with treadmills, elliptical machines, and weightlifting equipment.

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

₹11,592

₹13,258 total

includes taxes & fees

15 Nov - 16 Nov

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

A modern hotel lobby with a large digital display on the wall, a reception desk, a comfortable seating area with a sofa and cushions, and a clean, tiled floor.

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

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.

11. Courtyard by Marriott Tarrytown Westchester County

10.9 km from Pleasant Square

Syble

₹14,429

₹16,503 total

includes taxes & fees

1 Nov - 2 Nov

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

An outdoor patio area with tables and chairs, red umbrellas, and flower planters.

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

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

12. Hotel MTK Mount Kisco

13.2 km from Pleasant Square

eric w

₹13,933

₹15,936 total

includes taxes & fees

16 Nov - 17 Nov

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

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

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

13. Sheraton Tarrytown Hotel

11.4 km from Pleasant Square

Kerry-Anna

₹13,593

₹15,548 total

includes taxes & fees

8 Nov - 9 Nov

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

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

A modern lobby with a fireplace, bookshelves, and a seating area.

14. Residence Inn Orangeburg

15.4 km from Pleasant Square

KAREN

₹13,157

₹14,653 total

includes taxes & fees

8 Nov - 9 Nov

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

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

A modern building with a glass facade, a red door, and a staircase leading to the entrance.

15. Hotel Nyack, a JdV by Hyatt Hotel

9.5 km from Pleasant Square

Liana

₹10,062

₹14,080 total

includes taxes & fees

17 Nov - 18 Nov

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

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.

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

16. Days Inn by Wyndham Elmsford / White Plains

12.4 km from Pleasant Square

Frankie

₹10,898

₹12,796 total

includes taxes & fees

2 Nov - 3 Nov

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

A modern hotel reception area with a wooden reception desk, a sign reading "Hilton Honors," and a seating area with a patterned floor.

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.

17. Hilton Garden Inn Westchester Dobbs Ferry, NY

17.7 km from Pleasant Square

Mustafa

₹12,829

₹14,674 total

includes taxes & fees

1 Nov - 2 Nov

A checkered floor, a potted plant, and two metal ladders in a room with large windows.

A restaurant with a counter, stools, and a menu board.

A modern building with a glass facade, surrounded by a landscaped garden with various plants and a classical-style urn.

A modern office space with a large desk, multiple printers, and comfortable seating.

18. West Gate Inn Nyack

9.6 km from Pleasant Square

Stuart

₹9,084

₹10,389 total

includes taxes & fees

8 Nov - 9 Nov

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 coffee station with multiple coffee dispensers, a hot water station, and various coffee products on shelves.

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

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

14.4 km from Pleasant Square

Edwin

₹13,195

₹15,091 total

includes taxes & fees

15 Nov - 16 Nov

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

A Hampton Inn hotel with a clear sky and sunset.

A hotel room with a bed, a desk, a chair, a TV, and a painting on the wall.

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

20. Hampton Inn Nanuet

15.1 km from Pleasant Square

Leonard

₹11,598

₹13,497 total

includes taxes & fees

26 Oct - 27 Oct

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Top Pleasant Square Hotel Reviews

Hotel Edison Times Square

10/10 Excellent

"Centrally located in Theatre district and close to Times Square!"

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 studying the exhibits at Sing Sing Prison Museum 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 take a trip to 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 visit 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 visit 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 traveller data, and this hotel offers a restaurant and a 24-hour fitness centre. 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 should I expect to find near Pleasant Square?

Expedia has 36 hotels and other accommodation options 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, most hotel room reservations are refundable if you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before check in. If you have a non-refundable reservation, you might still have the option to cancel and receive a refund within 24 hours of booking. Plug in your dates, click on "Search", then filter by "fully refundable" to get the best deals near 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. 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.

Search Hotels Near Pleasant Square, Ossining

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Treat yourself

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Check prices for these dates

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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. Baymont by Wyndham White Plains - Elmsford

5. Element by Marriott Spring Valley

6. Ardsley Acres Hotel Westchester

7. SpringHill Suites by Marriott Tarrytown Westchester County

8. Cambria Hotel & Suites - White Plains Downtown

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

10. Hampton Inn White Plains/Tarrytown

11. Courtyard by Marriott Tarrytown Westchester County

12. Hotel MTK Mount Kisco

13. Sheraton Tarrytown Hotel

14. Residence Inn Orangeburg

15. Hotel Nyack, a JdV by Hyatt Hotel

16. Days Inn by Wyndham Elmsford / White Plains

17. Hilton Garden Inn Westchester Dobbs Ferry, NY

18. West Gate Inn Nyack

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

20. Hampton Inn Nanuet

Top Pleasant Square Hotel Reviews

Hotel Edison Times Square

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