The Best Hotels Closest to Pleasant Square in Ossining - 2026 Updated Prices

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 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 two-story house with a red door, white siding, and a brick pathway leading to the entrance.

1. Windrose On Hudson

3.1 km from Pleasant Square

Rachel

฿5,083

฿5,661 total

includes taxes & fees

8 Nov - 9 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 hotel room with a large bed, a bedside table with a lamp, a TV, and a bathroom with a mirror and sink.

2. DoubleTree by Hilton Hotel Nanuet

13.8 km from Pleasant Square

Linda

฿4,456

฿5,186 total

includes taxes & fees

18 Oct - 19 Oct

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

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

3. SpringHill Suites by Marriott Tarrytown Westchester County

11.2 km from Pleasant Square

Warren

฿5,238

฿5,991 total

includes taxes & fees

29 Oct - 30 Oct

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 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.

4. Element by Marriott Spring Valley

14.8 km from Pleasant Square

Danielle

฿4,800

฿5,586 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.

5. Westchester Marriott

11.7 km from Pleasant Square

Rosemary

฿6,626

฿7,579 total

includes taxes & fees

1 Nov - 2 Nov

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

6. Courtyard by Marriott Tarrytown Westchester County

10.9 km from Pleasant Square

Beth

฿5,113

฿5,847 total

includes taxes & fees

1 Nov - 2 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 motel with a gazebo in the front lawn, a signboard, and several parked cars.

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

7. Ardsley Acres Hotel Westchester

17.1 km from Pleasant Square

David

฿4,199

฿4,803 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 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.

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

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

8.5 km from Pleasant Square

Tammy

฿4,171

฿4,770 total

includes taxes & fees

15 Nov - 16 Nov

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

9. Cambria Hotel & Suites - White Plains Downtown

16.5 km from Pleasant Square

Gina

฿6,431

฿7,355 total

includes taxes & fees

8 Nov - 9 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 Sheraton hotel with a modern facade, multiple floors, and a prominent entrance.

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

10. Sheraton Tarrytown Hotel

11.4 km from Pleasant Square

Kerry-Anna

฿4,817

฿5,509 total

includes taxes & fees

1 Nov - 2 Nov

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.

11. Baymont by Wyndham White Plains - Elmsford

10.9 km from Pleasant Square

Amanda

฿4,603

฿5,265 total

includes taxes & fees

1 Nov - 2 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 Hampton Inn hotel with a clear sky and sunset.

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

12. Hampton Inn Nanuet

15.1 km from Pleasant Square

Ildar

฿3,834

฿4,461 total

includes taxes & fees

1 Nov - 2 Nov

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

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.

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.

13. Sonesta White Plains Downtown

17 km from Pleasant Square

Andrew

฿5,720

฿7,658 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.

14. Residence Inn Orangeburg

15.4 km from Pleasant Square

KAREN

฿4,662

฿5,192 total

includes taxes & fees

8 Nov - 9 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 building with a glass facade, a red door, and a staircase leading to the entrance.

A modern dining area with a wooden table, cushioned seating, pendant lighting, and a large window offering a view of the outdoors.

15. Hotel Nyack, a JdV by Hyatt Hotel

9.5 km from Pleasant Square

Jessica

฿3,678

฿5,118 total

includes taxes & fees

1 Nov - 2 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 spacious restaurant with high tables and stools, a bar area, and a television screen displaying a sports game.

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

16. Hotel MTK Mount Kisco

13.2 km from Pleasant Square

eric w

฿4,937

฿5,647 total

includes taxes & fees

15 Nov - 16 Nov

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.

17. Hilton Garden Inn Westchester Dobbs Ferry, NY

17.7 km from Pleasant Square

Qwawi

฿4,982

฿5,698 total

includes taxes & fees

1 Nov - 2 Nov

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 coffee station with two coffee machines and a variety of coffee pods and cups.

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

14.4 km from Pleasant Square

Edwin

฿4,406

฿5,040 total

includes taxes & fees

15 Nov - 16 Nov

A breakfast area with multiple tables and chairs, a kitchen area with appliances, and a sign for Daybreak Breakfast.

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

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

12.4 km from Pleasant Square

Frankie

฿3,861

฿4,534 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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

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

20. HYATT house White Plains

19.6 km from Pleasant Square

Laura Rebeca

฿5,975

฿6,834 total

includes taxes & fees

8 Nov - 9 Nov

View all properties

Compare popular hotels close to Pleasant Square

Property	Property class	Guest rating
Windrose On Hudson	8.6 Excellent 264 reviews	View
DoubleTree by Hilton Hotel Nanuet	9.0 Wonderful 1,195 reviews	View
SpringHill Suites by Marriott Tarrytown Westchester County	8.8 Excellent 1,006 reviews	View
Element by Marriott Spring Valley	9.0 Wonderful 548 reviews	View
Westchester Marriott	9.0 Wonderful 671 reviews	View

Top Pleasant Square Hotel Reviews

Radio Hotel

8/10 Good

"Clean room useful staff Location ok"

Empire Hotel

10/10 Excellent

"Bathroom amenities are sparse. Go prepared."

Capital Hotel

8/10 Good

"Very clean, modern hotel with helpful staff. There is no parking, but the hotel is a short walk from the nearest subway station. There is some fast food outlets, but no restaurants in the immediate area, to my knowledge. Manhattan is easily accessible via Lyft or Uber."

Hotel Belleclaire Central Park, a Small Luxury Hotel

10/10 Excellent

"Amazing stay ! Conveniently located near Beacon Theater. Very nice staff and rooms ."

Harmony Suites

10/10 Excellent

"La meilleure place avec un bon dejeuner compris. Des grandes chambre propres. Pas loins de time square en autobus. Facile d’acces. Grand stationnement. Le personnel est accueillant. J’ai voyager avec mes amies et ont s’est senti comme des reines :) merci Harmony Suite"

Park Central Hotel New York

8/10 Good

"None"

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.

See properties

Sing Sing Prison Museum

You can spend time studying the exhibits at Sing Sing Prison Museum 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 take a trip to 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 visit 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 visit 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 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 traveller data, and this hotel offers a restaurant and a 24-hour fitness centre. 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 should I expect to find near Pleasant Square?

Expedia has 36 hotels and other accommodation options 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, most hotel room reservations are refundable if you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before check in. If you have a non-refundable reservation, you might still have the option to cancel and receive a refund within 24 hours of booking. Plug in your dates, click on "Search", then filter by "fully refundable" to get the best deals near 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 Louis Engel Waterfront Park.

Search Hotels Near Pleasant Square, Ossining

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. DoubleTree by Hilton Hotel Nanuet

3. SpringHill Suites by Marriott Tarrytown Westchester County

4. Element by Marriott Spring Valley

5. Westchester Marriott

6. Courtyard by Marriott Tarrytown Westchester County

7. Ardsley Acres Hotel Westchester

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

9. Cambria Hotel & Suites - White Plains Downtown

10. Sheraton Tarrytown Hotel

11. Baymont by Wyndham White Plains - Elmsford

12. Hampton Inn Nanuet

13. Sonesta White Plains Downtown

14. Residence Inn Orangeburg

15. Hotel Nyack, a JdV by Hyatt Hotel

16. Hotel MTK Mount Kisco

17. Hilton Garden Inn Westchester Dobbs Ferry, NY

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

19. Days Inn by Wyndham Elmsford / White Plains

20. HYATT house White Plains

Compare popular hotels close to Pleasant Square

Top Pleasant Square Hotel Reviews

Radio Hotel

Empire Hotel

Capital Hotel

Hotel Belleclaire Central Park, a Small Luxury Hotel

Harmony Suites

Park Central Hotel New York

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