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

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

1.9 mi from Pleasant Square

Rachel

$163 nightly

$181 total

Nov 8 - Nov 9

Total with taxes and fees

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

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.

2. Summer Pool Oasis Custom Bar Arcade Pool Table

0.4 mi from Pleasant Square

$1,094 nightly

$1,219 total

Nov 3 - Nov 4

Total with taxes and fees

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

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

3. DoubleTree by Hilton Hotel Nanuet

8.5 mi from Pleasant Square

Linda

$135 nightly

$157 total

Oct 27 - Oct 28

Total with taxes and fees

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.

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

4. Element by Marriott Spring Valley

9.2 mi from Pleasant Square

Danielle

$143 nightly

$166 total

Oct 26 - Oct 27

Total with taxes and fees

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

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

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

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.

5. Baymont by Wyndham White Plains - Elmsford

6.7 mi from Pleasant Square

Heather

$135 nightly

$155 total

Nov 2 - Nov 3

Total with taxes and fees

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

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

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

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

5.3 mi from Pleasant Square

CHRISTY

$167 nightly

$191 total

Nov 12 - Nov 13

Total with taxes and fees

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

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

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.

7. Courtyard by Marriott Tarrytown Westchester County

6.8 mi from Pleasant Square

Justine

$152 nightly

$174 total

Nov 1 - Nov 2

Total with taxes and fees

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

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.

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

8. Cambria Hotel & Suites - White Plains Downtown

10.2 mi from Pleasant Square

Gina

$191 nightly

$219 total

Nov 8 - Nov 9

Total with taxes and fees

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

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 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.

9. SpringHill Suites by Marriott Tarrytown Westchester County

6.9 mi from Pleasant Square

Warren

$156 nightly

$178 total

Oct 18 - Oct 19

Total with taxes and fees

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 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.

10. Ardsley Acres Hotel Westchester

10.6 mi from Pleasant Square

David

$118 nightly

$135 total

Nov 11 - Nov 12

Total with taxes and fees

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

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.

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.

11. Sheraton Tarrytown Hotel

7.1 mi from Pleasant Square

Andrew

$143 nightly

$164 total

Nov 1 - Nov 2

Total with taxes and fees

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.

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

12. Hotel Nyack, a JdV by Hyatt Hotel

5.9 mi from Pleasant Square

Jessica

$135 nightly

$155 total

Nov 1 - Nov 2

Total with taxes and fees

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 Hampton Inn hotel with a clear sky and sunset.

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

13. Hampton Inn Nanuet

9.4 mi from Pleasant Square

Ildar

$114 nightly

$133 total

Nov 1 - Nov 2

Total with taxes and fees

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.

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

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

14. Hotel MTK Mount Kisco

8.2 mi from Pleasant Square

eric w

$155 nightly

$177 total

Nov 1 - Nov 2

Total with taxes and fees

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

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

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

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

15. Hilton Garden Inn Westchester Dobbs Ferry, NY

11 mi from Pleasant Square

Qwawi

$147 nightly

$168 total

Nov 1 - Nov 2

Total with taxes and fees

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 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.

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

8.9 mi from Pleasant Square

Edwin

$163 nightly

$186 total

Nov 11 - Nov 12

Total with taxes and fees

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

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.

A hotel room with a bed, a desk, a chair, a TV, and a lamp.

17. Sonesta Simply Suites Nanuet

9.4 mi from Pleasant Square

Susan

$105 nightly

$122 total

Oct 27 - Oct 28

Total with taxes and fees

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

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

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

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

18. HYATT house White Plains

12.2 mi from Pleasant Square

Justine

$178 nightly

$203 total

Nov 8 - Nov 9

Total with taxes and fees

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 with a brick facade, a covered walkway, and a parking lot.

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

19. Days Inn by Wyndham Elmsford / White Plains

7.7 mi from Pleasant Square

Frankie

$115 nightly

$135 total

Oct 25 - Oct 26

Total with taxes and fees

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

A hotel lobby with a sofa, armchairs, a glass table, and lamps.

20. West Gate Inn Nyack

5.9 mi from Pleasant Square

Stuart

$93 nightly

$107 total

Nov 9 - Nov 10

Total with taxes and fees

View all properties

Top Pleasant Square Hotel Reviews

Lotte New York Palace

10/10 Excellent

"Loved locations"

Hotel Edison Times Square

10/10 Excellent

"Room is smaller than expected. Some staff were friendly, some were not. Location was the best, as well as the complimentary breakfast."

The Belvedere Hotel

10/10 Excellent

"Not all rooms have been remodeled yet Breakfast could use additional options"

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

10/10 Excellent

"Property was a great location and very clean"

Pod Times Square

10/10 Excellent

"Proximity to Times Square, ease of check in, friendly staff and room comfort."

Hyatt Regency Times Square

8/10 Good

"The Crown has been redone by Hyatt. Hyatt has really done a great job of renewing the property. It has a nice clean look. Really like the new location of the restaurant/bar. They wait service in the restaurant/bar were very friendly, accommodating and helpful. I liked the room, especially the beds. they were very soft and comfortable. I found the check-in very cold and too business like. not very welcoming. We had a refrigerator in the room but no coffee maker which is something we really missed."

Hotel Belleclaire Central Park, a Small Luxury Hotel

8/10 Good

"Comfortable bed in VERY small room, especially for the high price. Bathroom nice with an excellent shower. Housekeeping only came once during our three night stay, which was a surprise. Lots of noise from hallway as the many nearby doors opened and closed many times. Liked the bar and bakery discount tickets, but the hotel was so packed that the bakery line was too long to wait for coffee a couple mornings. Location is excellent—many good dining options right on the block and subway is a block away."

Sheraton New York Times Square Hotel

10/10 Excellent

"Great location."

Harmony Suites

10/10 Excellent

"Nice place, pretty and decent breakfast"

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.

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Things to do in Nyack

Find hotels near Pleasant Square, Ossining from $107

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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. Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

7. Courtyard by Marriott Tarrytown Westchester County

8. Cambria Hotel & Suites - White Plains Downtown

9. SpringHill Suites by Marriott Tarrytown Westchester County

10. Ardsley Acres Hotel Westchester

11. Sheraton Tarrytown Hotel

12. Hotel Nyack, a JdV by Hyatt Hotel

13. Hampton Inn Nanuet

14. Hotel MTK Mount Kisco

15. Hilton Garden Inn Westchester Dobbs Ferry, NY

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

17. Sonesta Simply Suites Nanuet

18. HYATT house White Plains

19. Days Inn by Wyndham Elmsford / White Plains

20. West Gate Inn Nyack

Top Pleasant Square Hotel Reviews

Lotte New York Palace

Hotel Edison Times Square

The Belvedere Hotel

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

Pod Times Square

Hyatt Regency Times Square

Hotel Belleclaire Central Park, a Small Luxury Hotel

Sheraton New York Times Square Hotel

Harmony Suites

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

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