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 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

$164 nightly

$183 total

Nov 8 - Nov 9

Total with taxes and fees

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

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.

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

2. Westchester Marriott

7.3 mi from Pleasant Square

Karrie

$197 nightly

$225 total

Nov 8 - Nov 9

Total with taxes and fees

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

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.

3. Courtyard by Marriott Tarrytown Westchester County

6.8 mi from Pleasant Square

Syble

$152 nightly

$174 total

Nov 1 - Nov 2

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.

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.

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

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

Amanda

$135 nightly

$155 total

Nov 1 - Nov 2

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 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.

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

5.3 mi from Pleasant Square

Tammy

$141 nightly

$161 total

Nov 18 - Nov 19

Total with taxes and fees

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.

7. Cambria Hotel & Suites - White Plains Downtown

10.2 mi from Pleasant Square

Christine

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

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.

8. SpringHill Suites by Marriott Tarrytown Westchester County

6.9 mi from Pleasant Square

Warren

$156 nightly

$178 total

Oct 29 - Oct 30

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 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.

9. Sheraton Tarrytown Hotel

7.1 mi from Pleasant Square

Kerry-Anna

$143 nightly

$164 total

Nov 1 - Nov 2

Total with taxes and fees

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

7.4 mi from Pleasant Square

James

$122 nightly

$140 total

Nov 1 - Nov 2

Total with taxes and fees

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

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.

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.

11. Sonesta White Plains Downtown

10.5 mi from Pleasant Square

Andrew

$210 nightly

$241 total

Nov 8 - Nov 9

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

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

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

12. Ardsley Acres Hotel Westchester

10.6 mi from Pleasant Square

David

$121 nightly

$138 total

Nov 16 - Nov 17

Total with taxes and fees

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

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

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

9.5 mi from Pleasant Square

KAREN

$139 nightly

$154 total

Nov 8 - Nov 9

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

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.

14. HYATT house White Plains

12.2 mi from Pleasant Square

Laura Rebeca

$178 nightly

$203 total

Nov 8 - Nov 9

Total with taxes and fees

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

15. Hilton Garden Inn Westchester Dobbs Ferry, NY

11 mi from Pleasant Square

Mustafa

$157 nightly

$180 total

Nov 2 - Nov 3

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

$139 nightly

$159 total

Nov 15 - Nov 16

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.

17. Hotel Nyack, a JdV by Hyatt Hotel

5.9 mi from Pleasant Square

Liana

$138 nightly

$157 total

Nov 18 - Nov 19

Total with taxes and fees

A historic stone building with a turret, arched entrance, and a covered patio area.

A large, historic building with a red roof, surrounded by a well-maintained garden with statues and flower beds.

A spacious lobby with a staircase, seating area, and large windows offering a view of the outdoors.

A large building with a white facade and columns, surrounded by a lawn with outdoor seating and string lights.

18. Tarrytown House Estate

7.8 mi from Pleasant Square

Casey

$181 nightly

$207 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 gym with treadmills, exercise balls, and a yoga mat.

A Days Inn with a brick facade, a covered walkway, and a parking lot.

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

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 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.

20. West Gate Inn Nyack

5.9 mi from Pleasant Square

Stuart

$97 nightly

$111 total

Nov 8 - Nov 9

Total with taxes and fees

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Compare popular hotels close to Pleasant Square

Property	Star rating	Guest rating
Windrose On Hudson	8.6 Excellent 264 reviews	View
Westchester Marriott	9.0 Wonderful 674 reviews	View
Courtyard by Marriott Tarrytown Westchester County	9.0 Wonderful 1,001 reviews	View
Element by Marriott Spring Valley	9.0 Wonderful 549 reviews	View
Baymont by Wyndham White Plains - Elmsford	8.4 Very good 1,889 reviews	View

Top Pleasant Square Hotel Reviews

Night Hotel Broadway

10/10 Excellent

"The bronze rooms are outdated- while clean, we made the mistake of staying in a bronze our first time- it wasn't a great experience- this building needs some updating. There was chipping paint in the hallway staircase. There is no reason for that. A property so large should be able to handel re-painting a staircase. Have loved our stays in the silver rooms tho- much nicer and updated."

The Belvedere Hotel

10/10 Excellent

"very good"

Empire Hotel

10/10 Excellent

"Staff was attentive and quick to respond to any concern that came up. The location of this hotel is really what you pay for as you’re conveniently located a few steps away from Central Park, the Lincoln Center, and the major subway station in Columbus circle. I felt safe the entire stay and well taken care of as housekeeping came in everyday of our 5 day stay."

Hyatt Regency Times Square

10/10 Excellent

"The Hyatt Regency was amazing from the cleanliness of the property, excellent staff room size was very spacious our entire stay was fabulous. we are definitely staying at Hyatt Regency every chance we get when we are in New York City.!"

Pod Times Square

10/10 Excellent

"Compact but well organized room"

Capital Hotel

8/10 Good

"Clean room and easy check-in process. The bed is a little higher than you expect, and the sheets can be too tight and slip off sometimes, but it’s still a comfortable sleep in a good location for a reasonable price."

Hotel Edison Times Square

10/10 Excellent

"Best location for Broadway Show and Times Square. Room clean Good breakfast and a bottle of wine. Very helpful stuff ."

Hotel Belleclaire Central Park, a Small Luxury Hotel

10/10 Excellent

"Clean, well-maintained hotel in a nice neighborhood on the upper west side. Short walk to the subway and Central Park. We enjoyed the bar inside the hotel and the coffee shop next door. We would consider staying there 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.

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Find hotels near Pleasant Square, Ossining from $111

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Be picky

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Our top choices for Pleasant Square hotels

1. Windrose On Hudson

2. Westchester Marriott

3. Courtyard by Marriott Tarrytown Westchester County

4. Element by Marriott Spring Valley

5. Baymont by Wyndham White Plains - Elmsford

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

7. Cambria Hotel & Suites - White Plains Downtown

8. SpringHill Suites by Marriott Tarrytown Westchester County

9. Sheraton Tarrytown Hotel

10. Hampton Inn White Plains/Tarrytown

11. Sonesta White Plains Downtown

12. Ardsley Acres Hotel Westchester

13. Residence Inn Orangeburg

14. HYATT house White Plains

15. Hilton Garden Inn Westchester Dobbs Ferry, NY

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

17. Hotel Nyack, a JdV by Hyatt Hotel

18. Tarrytown House Estate

19. Days Inn by Wyndham Elmsford / White Plains

20. West Gate Inn Nyack

Compare popular hotels close to Pleasant Square

Top Pleasant Square Hotel Reviews

Night Hotel Broadway

The Belvedere Hotel

Empire Hotel

Hyatt Regency Times Square

Pod Times Square

Capital Hotel

Hotel Edison Times Square

Hotel Belleclaire Central Park, a Small Luxury Hotel

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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