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

SAR 617

SAR 687 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 modern living room with a sectional sofa, a coffee table, and large windows offering a view of trees.

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

SAR 2,027

SAR 4,038 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 modern restaurant interior with a bar area, seating, and a dessert display.

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

SAR 508

SAR 591 total

includes taxes & fees

12 Nov - 13 Nov

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

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

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

4. Westchester Marriott

11.7 km from Pleasant Square

Rosemary

SAR 740

SAR 846 total

includes taxes & fees

8 Nov - 9 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.

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

5. Element by Marriott Spring Valley

14.8 km from Pleasant Square

Danielle

SAR 537

SAR 625 total

includes taxes & fees

26 Oct - 27 Oct

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.

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.

6. Baymont by Wyndham White Plains - Elmsford

10.9 km from Pleasant Square

Amanda

SAR 508

SAR 581 total

includes taxes & fees

5 Nov - 6 Nov

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

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

7. Ardsley Acres Hotel Westchester

17.1 km from Pleasant Square

SAR 451

SAR 516 total

includes taxes & fees

12 Nov - 13 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.

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

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

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

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

8.5 km from Pleasant Square

Tammy

SAR 627

SAR 717 total

includes taxes & fees

12 Nov - 13 Nov

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

A buffet setup with various food items, a coffee station, and seating area.

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.

9. SpringHill Suites by Marriott Tarrytown Westchester County

11.2 km from Pleasant Square

Warren

SAR 585

SAR 669 total

includes taxes & fees

18 Oct - 19 Oct

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 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.

10. Courtyard by Marriott Tarrytown Westchester County

10.9 km from Pleasant Square

Justine

SAR 571

SAR 653 total

includes taxes & fees

1 Nov - 2 Nov

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.

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.

11. Hotel Nyack, a JdV by Hyatt Hotel

9.5 km from Pleasant Square

Jessica

SAR 411

SAR 572 total

includes taxes & fees

1 Nov - 2 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 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.

An indoor swimming pool with a 3 feet 10 inches deep sign, surrounded by a white tiled area, benches, and a glass door leading to another room.

12. Sheraton Tarrytown Hotel

11.4 km from Pleasant Square

Andrew

SAR 538

SAR 615 total

includes taxes & fees

12 Nov - 13 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 lobby with a red sofa set, a fireplace, and a staircase leading to an upper level.

13. Hotel MTK Mount Kisco

13.2 km from Pleasant Square

eric w

SAR 582

SAR 666 total

includes taxes & fees

1 Nov - 2 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 lobby with a reception desk, seating area, and a decorative wall.

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

14. Cambria Hotel & Suites - White Plains Downtown

16.5 km from Pleasant Square

Gina

SAR 718

SAR 821 total

includes taxes & fees

8 Nov - 9 Nov

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

15. Residence Inn Orangeburg

15.4 km from Pleasant Square

Jessica

SAR 521

SAR 580 total

includes taxes & fees

8 Nov - 9 Nov

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

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

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

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

16. Hampton Inn Nanuet

15.1 km from Pleasant Square

Ildar

SAR 428

SAR 498 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

A modern lobby with a large, tufted sofa, two armchairs, and a wooden coffee table. There are tall, cylindrical columns and a decorative wall with a geometric pattern.

17. Sonesta White Plains Downtown

17 km from Pleasant Square

Andrew

SAR 735

SAR 965 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 two coffee machines and a variety of coffee pods and cups.

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

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

14.4 km from Pleasant Square

Edwin

SAR 612

SAR 700 total

includes taxes & fees

11 Nov - 12 Nov

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

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

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.

19. West Gate Inn Nyack

9.6 km from Pleasant Square

Stuart

SAR 359

SAR 411 total

includes taxes & fees

8 Nov - 9 Nov

A hotel entrance with a sign reading "SONESTA Simply Suites".

A covered outdoor area with a wooden deck, metal chairs, a round table, and hanging flower baskets.

A compact kitchen with a dining area, a flat-screen TV, a microwave, a coffee maker, and a refrigerator.

A modern living room with a dark wood floor, a large round table, and a sofa. There is a kitchen area with dark cabinetry and a refrigerator.

20. Sonesta Simply Suites Nanuet

15.1 km from Pleasant Square

Susan

SAR 393

SAR 458 total

includes taxes & fees

28 Oct - 29 Oct

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Top Pleasant Square Hotel Reviews

Empire Hotel

8/10 Good

"Location is great"

Hotel Edison Times Square

10/10 Excellent

"Very clean"

Hotel Belleclaire Central Park, a Small Luxury Hotel

8/10 Good

"It’s a cute, clean hotel and the air conditioning is quiet and works well. There are basically no amenities, though. I couldn’t even get a wine glass for my room, even though there is a bar downstairs. They offered me a paper cup. No robes, or q tips either… basically just a bar of soap. It worked fine for what we needed but it definitely doesn’t feel luxurious. And the $10 breakfast vouchers to use at the cafe downstairs are nice but the only gluten free options were a tiny muffin or a macaron, which was disappointing. The elevators are also extremely small and slow. They fit two people comfortably, anything more than that is awkward."

ROW NYC

8/10 Good

"The location is superb. The subway is close by and there is lots to see within walking distance. Definitely a great place to stay in the city."

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

8/10 Good

"The hotel needs to be updated with amenities in and outside the room. Also because of the construction there's no sign, you will miss looking for the location. Hilton put a plastic sign up for members to know where the hotel is located under all the construction."

Radio Hotel

10/10 Excellent

"It's a well laid out small space. It was everything I needed for a one night stay. The staff was also very nice and welcoming. The drink tickets were also a nice perk!"

The Belvedere Hotel

8/10 Good

"Clean room, nice staff, small elevators, good location"

Lotte New York Palace

10/10 Excellent

"We have stayed here several times before and we loved it just as much! The staff are very welcoming and helpful. The hotel is beautiful and the bars are unmatched. The location is wonderful for getting to restaurants or sight seeing. We will absolutely stay here again!"

Pod 51

8/10 Good

"It was very nice. Loved the receptionists, they let us check in early!"

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 SAR 411

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Treat yourself

Be picky

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. Westchester Marriott

5. Element by Marriott Spring Valley

6. Baymont by Wyndham White Plains - Elmsford

7. Ardsley Acres Hotel Westchester

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

9. SpringHill Suites by Marriott Tarrytown Westchester County

10. Courtyard by Marriott Tarrytown Westchester County

11. Hotel Nyack, a JdV by Hyatt Hotel

12. Sheraton Tarrytown Hotel

13. Hotel MTK Mount Kisco

14. Cambria Hotel & Suites - White Plains Downtown

15. Residence Inn Orangeburg

16. Hampton Inn Nanuet

17. Sonesta White Plains Downtown

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

19. West Gate Inn Nyack

20. Sonesta Simply Suites Nanuet

Top Pleasant Square Hotel Reviews

Empire Hotel

Hotel Edison Times Square

Hotel Belleclaire Central Park, a Small Luxury Hotel

ROW NYC

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

Radio Hotel

The Belvedere Hotel

Lotte New York Palace

Pod 51

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