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

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Our top choices for Pleasant Square hotels

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.

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

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

1. Baymont by Wyndham White Plains - Elmsford

6.7 mi from Pleasant Square

Ebony

£124

includes taxes & fees

12 Oct - 13 Oct

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 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.

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

5.3 mi from Pleasant Square

CHRISTY

£147

includes taxes & fees

18 Oct - 19 Oct

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.

3. Hotel MTK Mount Kisco

8.2 mi from Pleasant Square

Patricia

£127

includes taxes & fees

11 Oct - 12 Oct

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

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

4. DoubleTree by Hilton Hotel Nanuet

8.5 mi from Pleasant Square

Linda

£115

includes taxes & fees

27 Oct - 28 Oct

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.

5. Ardsley Acres Hotel Westchester

10.6 mi from Pleasant Square

David

£97

includes taxes & fees

30 Sept - 1 Oct

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

6. Hotel Nyack, a JdV by Hyatt Hotel

5.9 mi from Pleasant Square

Jessica

£140

includes taxes & fees

26 Oct - 27 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 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 bar area with a long counter, multiple chairs, and a television mounted on the wall.

7. SpringHill Suites by Marriott Tarrytown Westchester County

6.9 mi from Pleasant Square

ERIC

£134

includes taxes & fees

4 Oct - 5 Oct

A modern kitchen with a large island, bar stools, a flat-screen TV, and a stone backsplash.

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

A lobby with teal patterned chairs, a fireplace, and a flat-screen TV mounted above it.

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

8. Hampton Inn White Plains/Tarrytown

7.4 mi from Pleasant Square

Susan

£124

includes taxes & fees

12 Oct - 13 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.

An outdoor patio with stone walls, a fire pit, and seating.

9. Element by Marriott Spring Valley

9.2 mi from Pleasant Square

Kenneth

£126

includes taxes & fees

12 Oct - 13 Oct

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

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

An indoor swimming pool with a 'NO DIVING' sign, lounge chairs, and a lifeguard chair.

10. Residence Inn Orangeburg

9.5 mi from Pleasant Square

Jessica

£135

includes taxes & fees

25 Oct - 26 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 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.

11. Courtyard by Marriott Tarrytown Westchester County

6.8 mi from Pleasant Square

Syble

£155

includes taxes & fees

18 Oct - 19 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 two coffee machines and a variety of coffee pods and cups.

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.

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

8.9 mi from Pleasant Square

Dexter

£136

includes taxes & fees

7 Oct - 8 Oct

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

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

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.

13. Tarrytown House Estate

7.8 mi from Pleasant Square

RAMESH

£156

includes taxes & fees

4 Oct - 5 Oct

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

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

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.

14. West Gate Inn Nyack

5.9 mi from Pleasant Square

Wendell

£88

includes taxes & fees

12 Oct - 13 Oct

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.

15. Sonesta White Plains Downtown

10.5 mi from Pleasant Square

Tamara

£188

includes taxes & fees

29 Oct - 30 Oct

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.

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.

16. HYATT house White Plains

12.2 mi from Pleasant Square

Charles

£175

includes taxes & fees

22 Oct - 23 Oct

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.

17. Sheraton Tarrytown Hotel

7.1 mi from Pleasant Square

Wayne

£144

includes taxes & fees

26 Oct - 27 Oct

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

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.

A covered outdoor area with a wooden deck, metal chairs, a round table, and hanging flower baskets.

18. Sonesta Simply Suites Nanuet

9.4 mi from Pleasant Square

Theresa

£106

includes taxes & fees

26 Oct - 27 Oct

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.

19. Hilton Garden Inn Westchester Dobbs Ferry, NY

11 mi from Pleasant Square

Qwawi

£131

includes taxes & fees

26 Oct - 27 Oct

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 modern hotel lobby with a long communal table, seating area, and a kitchenette.

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

20. Hampton Inn Nanuet

9.4 mi from Pleasant Square

Ildar

£100

includes taxes & fees

18 Oct - 19 Oct

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Compare popular hotels close to Pleasant Square

Property	Property class	Guest rating
Baymont by Wyndham White Plains - Elmsford	8.4 Very good 1,868 reviews	View
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG	9.0 Wonderful 1,004 reviews	View
Hotel MTK Mount Kisco	8.6 Excellent 1,007 reviews	View
DoubleTree by Hilton Hotel Nanuet	9.0 Wonderful 1,196 reviews	View
Ardsley Acres Hotel Westchester	8.8 Excellent 1,188 reviews	View

Top Pleasant Square Hotel Reviews

ROW NYC

10/10 Excellent

"Staff member (Yarah...I think) saved the day when I had issues with my transfer with Elife Limos. She went over and above. I was so upset and anxious but she sorted it! Would definitely return. Our bedroom was a good size too."

Hotel Belleclaire Central Park, a Small Luxury Hotel

10/10 Excellent

"Nice property. Our first stay in NYC Highly recommend."

Empire Hotel

8/10 Good

"Great Location! Can walk to many popular parts of the city, no problem and is near olumus Circle station which basically connects you to everywhere. Would stay again"

Harmony Suites

8/10 Good

"Everything was perfect except for the channels on the tv some were working but majority wasn’t. Someone was sent up to fix it but that didn’t help either"

Radio Hotel

10/10 Excellent

"The place is so good, spacious and have value for money. The clean room is so good"

Hotel Edison Times Square

10/10 Excellent

"Great location, we had connecting room for our family. Had to pay extra for small refrigerator for baby’s milk but whatever. If we wanted to check in early we had to pay so we waited then the room wasn’t ready so that didn’t make good sense. Mom the less great trip"

Park Lane New York

8/10 Good

"great location"

Pod Times Square

10/10 Excellent

"Good bar. Clean bunk beds."

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

10/10 Excellent

"amazing service, spacious and clean room/ bathroom. we had a great time here!"

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 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 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 37 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 Croton Landing Park.

Search Hotels Near Pleasant Square, Ossining

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Our top choices for Pleasant Square hotels

1. Baymont by Wyndham White Plains - Elmsford

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

3. Hotel MTK Mount Kisco

4. DoubleTree by Hilton Hotel Nanuet

5. Ardsley Acres Hotel Westchester

6. Hotel Nyack, a JdV by Hyatt Hotel

7. SpringHill Suites by Marriott Tarrytown Westchester County

8. Hampton Inn White Plains/Tarrytown

9. Element by Marriott Spring Valley

10. Residence Inn Orangeburg

11. Courtyard by Marriott Tarrytown Westchester County

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

13. Tarrytown House Estate

14. West Gate Inn Nyack

15. Sonesta White Plains Downtown

16. HYATT house White Plains

17. Sheraton Tarrytown Hotel

18. Sonesta Simply Suites Nanuet

19. Hilton Garden Inn Westchester Dobbs Ferry, NY

20. Hampton Inn Nanuet

Compare popular hotels close to Pleasant Square

Top Pleasant Square Hotel Reviews

ROW NYC

Hotel Belleclaire Central Park, a Small Luxury Hotel

Empire Hotel

Harmony Suites

Radio Hotel

Hotel Edison Times Square

Park Lane New York

Pod Times Square

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

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