Top 10 Hotels Near Pleasant Square in Ossining for 2026

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Pleasant Square hotels

A hotel room with a large bed, two bedside lamps, a nightstand, a blue chair, and a view of greenery through the window.

A conference room with a large screen displaying a building image, a whiteboard, and a table with laptops, papers, and coffee cups.

A stone fireplace with a fire, surrounded by outdoor seating.

A spacious indoor area with large windows, modern furniture, and a view of a landscaped outdoor area.

1. Windrose On Hudson

3.1 km from Pleasant Square

Rachel

P13,334

P14,851 total

includes taxes & fees

Sep 27 - Sep 28

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 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.

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

8.5 km from Pleasant Square

schuyler

P10,647

P12,178 total

includes taxes & fees

Oct 25 - Oct 26

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

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

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.

3. Baymont by Wyndham White Plains - Elmsford

10.9 km from Pleasant Square

Ebony

P8,997

P10,290 total

includes taxes & fees

Oct 1 - Oct 2

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

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

4. Ardsley Acres Hotel Westchester

17.1 km from Pleasant Square

David

P7,008

P8,016 total

includes taxes & fees

Sep 29 - Sep 30

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.

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

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

5. Hotel MTK Mount Kisco

13.2 km from Pleasant Square

Patricia

P9,205

P10,529 total

includes taxes & fees

Oct 11 - Oct 12

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.

6. Westchester Marriott

11.7 km from Pleasant Square

Donna

P12,191

P13,944 total

includes taxes & fees

Oct 18 - Oct 19

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 flat-screen TV on a wooden dresser, a sofa, a bed with a white headboard, and two abstract paintings 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 hotel room with a bed, a desk with a chair, a TV, and artwork on the walls.

7. SpringHill Suites by Marriott Tarrytown Westchester County

11.2 km from Pleasant Square

ERIC

P9,754

P11,156 total

includes taxes & fees

Oct 18 - Oct 19

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 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.

8. Courtyard by Marriott Tarrytown Westchester County

10.9 km from Pleasant Square

Gabriella

P11,211

P12,823 total

includes taxes & fees

Oct 4 - Oct 5

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

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.

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

9. Cambria Hotel & Suites - White Plains Downtown

16.5 km from Pleasant Square

Aylissia

P13,979

P15,989 total

includes taxes & fees

Oct 18 - Oct 19

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.

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

10. Sheraton Tarrytown Hotel

11.4 km from Pleasant Square

Desorene

P10,973

P12,550 total

includes taxes & fees

Oct 1 - Oct 2

An indoor swimming pool with clear glass ceilings, stone walls, and multiple lounge chairs around the pool area.

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 hotel dining area with multiple tables and chairs, a bar with a counter and bar stools, and two televisions mounted on the wall.

11. DoubleTree by Hilton Hotel Nanuet

13.8 km from Pleasant Square

Linda

P8,114

P9,443 total

includes taxes & fees

Oct 12 - Oct 13

A modern hotel entrance with a glass door, a car parked outside, and a well-lit pathway leading to the entrance.

A modern lounge area with sofas, armchairs, and a bar.

A spa room with a massage table, a circular hot tub, and candles.

An indoor swimming pool with multiple lounge chairs and a skylight.

12. The Opus Westchester, Autograph Collection

16.4 km from Pleasant Square

patricia

P18,727

P23,568 total

includes taxes & fees

Oct 4 - Oct 5

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

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

13. HYATT house White Plains

19.6 km from Pleasant Square

Charles

P12,457

P14,248 total

includes taxes & fees

Oct 1 - Oct 2

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 hotel room with a bed, a sofa, a nightstand, a lamp, and a framed picture on the wall.

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

14. Hampton Inn White Plains/Tarrytown

12 km from Pleasant Square

Kenjay

P8,063

P9,222 total

includes taxes & fees

Oct 1 - Oct 2

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

A spacious lobby with a high ceiling, patterned walls, and a central seating area with ottomans and a coffee table.

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.

15. Tarrytown House Estate

12.5 km from Pleasant Square

RAMESH

P9,958

P12,956 total

includes taxes & fees

Oct 4 - Oct 5

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

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.

A hotel room with two beds, a desk with a television, and a window with curtains.

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

14.4 km from Pleasant Square

Dexter

P10,334

P11,820 total

includes taxes & fees

Oct 7 - Oct 8

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.

17. Element by Marriott Spring Valley

14.8 km from Pleasant Square

Michaelle

P8,198

P9,541 total

includes taxes & fees

Oct 4 - Oct 5

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

18. Residence Inn Orangeburg

15.4 km from Pleasant Square

Jessica

P10,090

P11,238 total

includes taxes & fees

Oct 18 - Oct 19

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.

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

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

19. Sonesta White Plains Downtown

17 km from Pleasant Square

Tamara

P11,840

P15,620 total

includes taxes & fees

Oct 25 - Oct 26

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

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.

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

20. West Gate Inn Nyack

9.6 km from Pleasant Square

Wendell

P7,265

P8,309 total

includes taxes & fees

Sep 27 - Sep 28

View all properties

Compare popular hotels close to Pleasant Square

Property	Property class	Guest rating
Windrose On Hudson	8.6 Excellent 245 reviews	View
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG	9.0 Wonderful 1,000 reviews	View
Baymont by Wyndham White Plains - Elmsford	8.4 Very good 1,855 reviews	View
Ardsley Acres Hotel Westchester	8.8 Excellent 1,177 reviews	View
Hotel MTK Mount Kisco	8.6 Excellent 1,001 reviews	View

Top Pleasant Square Hotel Reviews

Warwick New York

10/10 Excellent

"Everything was great! The staff in particular were very kind and helpful."

Harmony Suites

8/10 Good

"The breakfast buffet was awesome and better than anticipated. The room was clean but lacked adequate toilet tissue and when we asked housekeeping (she was right next door), we were told the request had to be passed through the front desk.... In addition, there were signs throughout the hotel and outside on the property threatening stiff fines for really minor infractions. Draconian comes to mind."

Hotel Belleclaire Central Park, a Small Luxury Hotel

8/10 Good

"No hand soap by the sink."

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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 37 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 37 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.

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 Croton Landing Park.

Hotels near Pleasant Square

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Pleasant Square hotels

1. Windrose On Hudson

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

3. Baymont by Wyndham White Plains - Elmsford

4. Ardsley Acres Hotel Westchester

5. Hotel MTK Mount Kisco

6. Westchester Marriott

7. SpringHill Suites by Marriott Tarrytown Westchester County

8. Courtyard by Marriott Tarrytown Westchester County

9. Cambria Hotel & Suites - White Plains Downtown

10. Sheraton Tarrytown Hotel

11. DoubleTree by Hilton Hotel Nanuet

12. The Opus Westchester, Autograph Collection

13. HYATT house White Plains

14. Hampton Inn White Plains/Tarrytown

15. Tarrytown House Estate

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

17. Element by Marriott Spring Valley

18. Residence Inn Orangeburg

19. Sonesta White Plains Downtown

20. West Gate Inn Nyack

Compare popular hotels close to Pleasant Square

Top Pleasant Square Hotel Reviews

Warwick New York

Harmony Suites

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