Hotels closest to Pleasant Square in Ossining

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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 gym with treadmills, a red carpet, and exercise equipment.

A conference room with multiple tables and chairs, a projector, and a presentation screen.

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

€150

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

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.

2. DoubleTree by Hilton Hotel Nanuet

13.8 km from Pleasant Square

Linda

€140

includes taxes & fees

27 Oct - 28 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 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.

3. Element by Marriott Spring Valley

14.8 km from Pleasant Square

Danielle

€149

includes taxes & fees

26 Oct - 27 Oct

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

Robert

€190

includes taxes & fees

1 Nov - 2 Nov

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 bed, a desk with a chair, a TV, and artwork on the walls.

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.

5. SpringHill Suites by Marriott Tarrytown Westchester County

11.2 km from Pleasant Square

Warren

€159

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

6. Courtyard by Marriott Tarrytown Westchester County

10.9 km from Pleasant Square

Justine

€155

includes taxes & fees

1 Nov - 2 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 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.

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

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

8.5 km from Pleasant Square

Maureen

€171

includes taxes & fees

12 Nov - 13 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 modern office space with two monitors, a white desk, black chairs, and a large abstract painting on the wall.

A gym with exercise equipment, large windows, and a wooden reception desk.

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

8. Sheraton Tarrytown Hotel

11.4 km from Pleasant Square

Andrew

€146

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 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.

9. Hotel Nyack, a JdV by Hyatt Hotel

9.5 km from Pleasant Square

Jessica

€138

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 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

17.1 km from Pleasant Square

David

€125

includes taxes & fees

13 Oct - 14 Oct

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.

11. Baymont by Wyndham White Plains - Elmsford

10.9 km from Pleasant Square

Heather

€138

includes taxes & fees

2 Nov - 3 Nov

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

12. Cambria Hotel & Suites - White Plains Downtown

16.5 km from Pleasant Square

Gina

€195

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 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.

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

13. Hampton Inn Nanuet

15.1 km from Pleasant Square

Ildar

€118

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.

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 hotel entrance with a covered walkway, stone pillars, and potted plants.

14. Hotel MTK Mount Kisco

13.2 km from Pleasant Square

eric w

€158

includes taxes & fees

1 Nov - 2 Nov

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 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.

15. Sonesta White Plains Downtown

17 km from Pleasant Square

Andrew

€208

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 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.

16. Sonesta Simply Suites Nanuet

15.1 km from Pleasant Square

Susan

€113

includes taxes & fees

26 Oct - 27 Oct

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.

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

14.4 km from Pleasant Square

Edwin

€158

includes taxes & fees

9 Nov - 10 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.

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

18. Residence Inn Orangeburg

15.4 km from Pleasant Square

Jessica

€138

includes taxes & fees

8 Nov - 9 Nov

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.

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.

19. HYATT house White Plains

19.6 km from Pleasant Square

Justine

€181

includes taxes & fees

8 Nov - 9 Nov

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

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

20. Days Inn by Wyndham Elmsford / White Plains

12.4 km from Pleasant Square

Frankie

€120

includes taxes & fees

25 Oct - 26 Oct

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Compare popular hotels close to Pleasant Square

Property	Property class	Guest rating
Windrose On Hudson	8.6 Excellent 258 reviews	View
DoubleTree by Hilton Hotel Nanuet	9.0 Wonderful 1,194 reviews	View
Element by Marriott Spring Valley	9.0 Wonderful 546 reviews	View
Westchester Marriott	9.0 Wonderful 670 reviews	View
SpringHill Suites by Marriott Tarrytown Westchester County	8.8 Excellent 1,001 reviews	View

Top Pleasant Square Hotel Reviews

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."

Capital Hotel

10/10 Excellent

"Good hotel!!! Good hotel!!"

ROW NYC

8/10 Good

"Would have liked a coffee maker in the room"

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

10/10 Excellent

"Nice and convenient place to stay."

Sheraton New York Times Square Hotel

10/10 Excellent

"Great location."

Hyatt Regency Times Square

8/10 Good

"Falta un poco de limpieza en las habitaciones. También son algo ruidosas. Fuera de eso la ubicación y el personal es excelente."

Harmony Suites

10/10 Excellent

"Nice place, pretty and decent breakfast"

Pod 51

10/10 Excellent

"Excellent hotel/hostel. I chose a room with a shared bathroom, and the stay was excellent; I encountered no problems, and the space remained consistently clean."

Park Central Hotel New York

10/10 Excellent

"Very pleasant place"

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 studying the exhibits at Sing Sing Prison Museum 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 take a trip to 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 visit 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 visit 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 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.

Ossining Hotel Guide - Pleasant Square hotels in Ossining, United States of America.

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Treat yourself

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Check prices for these dates

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Our top choices for Pleasant Square hotels

1. Windrose On Hudson

2. DoubleTree by Hilton Hotel Nanuet

3. Element by Marriott Spring Valley

4. Westchester Marriott

5. SpringHill Suites by Marriott Tarrytown Westchester County

6. Courtyard by Marriott Tarrytown Westchester County

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

8. Sheraton Tarrytown Hotel

9. Hotel Nyack, a JdV by Hyatt Hotel

10. Ardsley Acres Hotel Westchester

11. Baymont by Wyndham White Plains - Elmsford

12. Cambria Hotel & Suites - White Plains Downtown

13. Hampton Inn Nanuet

14. Hotel MTK Mount Kisco

15. Sonesta White Plains Downtown

16. Sonesta Simply Suites Nanuet

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

18. Residence Inn Orangeburg

19. HYATT house White Plains

20. Days Inn by Wyndham Elmsford / White Plains

Compare popular hotels close to Pleasant Square

Top Pleasant Square Hotel Reviews

Hotel Belleclaire Central Park, a Small Luxury Hotel

Capital Hotel

ROW NYC

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

Sheraton New York Times Square Hotel

Hyatt Regency Times Square

Harmony Suites

Pod 51

Park Central Hotel New York

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