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 large windows, modern furniture, and a view of a landscaped outdoor area.

A modern building with a brick facade, large windows, and a covered outdoor seating area with tables and chairs.

A hotel lobby with a large digital map display, comfortable seating areas, and a reception desk.

A cafe with brick walls, a wooden counter, and a window with natural light.

1. Windrose On Hudson

3.1 km from Pleasant Square

Margaret

￥23,705

￥26,401 total

includes taxes & fees

Nov 8 - Nov 9

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

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

2. Summer Pool Oasis Custom Bar Arcade Pool Table

0.7 km from Pleasant Square

￥72,458

￥155,060 total

includes taxes & fees

Nov 4 - Nov 5

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

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 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

Barbara

￥19,868

￥23,122 total

includes taxes & fees

Nov 22 - Nov 23

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

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

4. Sheraton Tarrytown Hotel

11.4 km from Pleasant Square

Kerry-Anna

￥21,209

￥24,257 total

includes taxes & fees

Nov 22 - Nov 23

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

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.

5. SpringHill Suites by Marriott Tarrytown Westchester County

11.2 km from Pleasant Square

Warren

￥24,429

￥27,941 total

includes taxes & fees

Nov 1 - Nov 2

An outdoor seating area with wicker chairs and tables, surrounded by greenery and a modern lamp structure.

A bar area with a long counter, multiple shelves with bottles, and several bar stools.

A formal dining setup with multiple tables, each set with clear glassware, plates, and cutlery.

A modern lobby with a reception desk, seating area, and a kitchen in the background.

6. Westchester Marriott

11.7 km from Pleasant Square

Karrie

￥28,080

￥32,116 total

includes taxes & fees

Nov 22 - Nov 23

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.

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

7. Element by Marriott Spring Valley

14.8 km from Pleasant Square

Danielle

￥21,021

￥24,463 total

includes taxes & fees

Nov 22 - Nov 23

A Holiday Inn Express & Suites sign with a bench and flower beds in front.

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

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 hotel room with a bed, bedside tables, a desk, a lamp, a painting, and a bathroom with a bathtub and sink.

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

14.4 km from Pleasant Square

John

￥20,550

￥23,504 total

includes taxes & fees

Nov 22 - Nov 23

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.

9. Ardsley Acres Hotel Westchester

17.1 km from Pleasant Square

Wendell

￥18,251

￥20,875 total

includes taxes & fees

Nov 26 - Nov 27

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.

10. Cambria Hotel & Suites - White Plains Downtown

16.5 km from Pleasant Square

Anthony

￥29,994

￥34,305 total

includes taxes & fees

Nov 22 - Nov 23

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.

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.

11. Baymont by Wyndham White Plains - Elmsford

10.9 km from Pleasant Square

Amanda

￥21,201

￥24,248 total

includes taxes & fees

Nov 15 - Nov 16

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.

12. Residence Inn Orangeburg

15.4 km from Pleasant Square

KAREN

￥23,154

￥25,788 total

includes taxes & fees

Nov 8 - Nov 9

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 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.

13. Courtyard by Marriott Tarrytown Westchester County

10.9 km from Pleasant Square

Syble

￥23,844

￥27,270 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 hotel entrance with a covered walkway, stone pillars, and potted plants.

A spacious lobby with a red sofa set, 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.

14. Hotel MTK Mount Kisco

13.2 km from Pleasant Square

eric w

￥21,096

￥24,129 total

includes taxes & fees

Nov 9 - Nov 10

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

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.

A Hampton Inn hotel with a clear sky and sunset.

15. Hampton Inn Nanuet

15.1 km from Pleasant Square

Leonard

￥16,594

￥19,311 total

includes taxes & fees

Nov 1 - Nov 2

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

16. Hotel Nyack, a JdV by Hyatt Hotel

9.5 km from Pleasant Square

Liana

￥16,628

￥23,268 total

includes taxes & fees

Nov 22 - Nov 23

An outdoor seating area with modern furniture, a fire pit, and ambient lighting.

A hotel entrance with a glass door, a blue-lit entrance, and a skylight above.

A modern bar area with a long counter, multiple stools, and a bar stocked with bottles.

An indoor swimming pool with clear water, surrounded by lounge chairs and a seating area.

17. Sonesta White Plains Downtown

17 km from Pleasant Square

Andrew

￥22,950

￥31,452 total

includes taxes & fees

Nov 22 - Nov 23

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

A hotel room with two beds, a blue sofa, a wooden coffee table, and a painting on the wall.

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

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

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

8.5 km from Pleasant Square

Sean P.

￥21,648

￥24,760 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.

A multi-story hotel with a prominent 'Hyatt House' sign, surrounded by well-maintained lawns and trees.

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

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

19. HYATT house White Plains

19.6 km from Pleasant Square

Brandi

￥27,868

￥31,873 total

includes taxes & fees

Nov 15 - Nov 16

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

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

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

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

20. Hilton Garden Inn Westchester Dobbs Ferry, NY

17.7 km from Pleasant Square

Mustafa

￥21,201

￥24,249 total

includes taxes & fees

Nov 15 - Nov 16

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Top Pleasant Square Hotel Reviews

Park Central Hotel New York

10/10 Excellent

"A comfortable stay..Thank you!!"

Pod Times Square

8/10 Good

"Free walking tour around Central Park was good,"

Harmony Suites

10/10 Excellent

"Very clean, great staff, wonderful breakfast. Will definitely stay here again!"

ROW NYC

8/10 Good

"Room was clean and the hotel was in great shape. Smelled great with what ever fragrance they pump in that place."

Sheraton New York Times Square Hotel

10/10 Excellent

"The bed...OMG the bed is so comfortable after walking 12 hours your body melts into the bed"

Hotel Belleclaire Central Park, a Small Luxury Hotel

10/10 Excellent

"Outstanding UWS location, and staff was remarkably attentive. I emailed numerous times about restaurant recommendations, public transit information, and responses were immediate and informative. Wine & Jazz from 5-6 was a splendid touch, and the breakfast credit at the exceptional patisserie adjacent was very welcome. Clean room, firm bed, what’s not to like?"

Radio Hotel

10/10 Excellent

"So clean! Friendly staff. Room was adorable. Rooftop bar view amazing!"

Hilton Garden Inn New York/Central Park South-Midtown West

10/10 Excellent

"Excellent location. Clean rooms, friendly staff. Would stay again!"

The Manhattan Club

8/10 Good

"It was a really nice hotel. It was clean and close to Carnegie Hall which we were going to one night and close to Central Park and Columbus Square. We got in at 1:30 and our room wasn't ready. We had to bee in Brooklyn so they held our luggage for us and when we got back at 10pm we checked into our room. It had many amenities. The lounge was nice but bright and not intimate. The rooms were like tiny apartments. My only issue was with some of the bell men. We gave one guy $20 to hold our luggage and then bring it to our room when we could get in. He just took the money and passed off the work to other bellmen. The next morning we were ordering an lyft and he wanted us to take their driver which was $25 more than a lyft. I would stay there again if we were doing something in the city."

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 ￥19,311

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Treat yourself

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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. Sheraton Tarrytown Hotel

5. SpringHill Suites by Marriott Tarrytown Westchester County

6. Westchester Marriott

7. Element by Marriott Spring Valley

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

9. Ardsley Acres Hotel Westchester

10. Cambria Hotel & Suites - White Plains Downtown

11. Baymont by Wyndham White Plains - Elmsford

12. Residence Inn Orangeburg

13. Courtyard by Marriott Tarrytown Westchester County

14. Hotel MTK Mount Kisco

15. Hampton Inn Nanuet

16. Hotel Nyack, a JdV by Hyatt Hotel

17. Sonesta White Plains Downtown

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

19. HYATT house White Plains

20. Hilton Garden Inn Westchester Dobbs Ferry, NY

Top Pleasant Square Hotel Reviews

Park Central Hotel New York

Pod Times Square

Harmony Suites

ROW NYC

Sheraton New York Times Square Hotel

Hotel Belleclaire Central Park, a Small Luxury Hotel

Radio Hotel

Hilton Garden Inn New York/Central Park South-Midtown West

The Manhattan Club

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