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

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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 group of people playing a wooden block game outdoors near a stone building with a fire feature.

A hotel lobby with a reception desk, a seating area with a table, and potted plants.

A spacious room with a high arched ceiling and rows of green chairs.

1. Windrose On Hudson

1.9 mi from Pleasant Square

Rachel

£175

includes taxes & fees

28 Oct - 29 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 room with a large bed, a desk, and a chair. There is a window with curtains and a wall with a geometric patterned design.

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

2. Baymont by Wyndham White Plains - Elmsford

6.7 mi from Pleasant Square

Ebony

£124

includes taxes & fees

5 Oct - 6 Oct

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

A spacious lobby with a central seating area, a decorative wall, and a reception desk in the background.

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

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

3. DoubleTree by Hilton Hotel Nanuet

8.5 mi from Pleasant Square

Linda

£115

includes taxes & fees

27 Oct - 28 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 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.

A Holiday Inn Express & Suites hotel with a modern design, featuring a covered entrance and American flags.

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

5. Hotel MTK Mount Kisco

8.2 mi from Pleasant Square

Patricia

£127

includes taxes & fees

11 Oct - 12 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.

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.

6. Element by Marriott Spring Valley

9.2 mi from Pleasant Square

Kenneth

£126

includes taxes & fees

12 Oct - 13 Oct

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.

7. Ardsley Acres Hotel Westchester

10.6 mi from Pleasant Square

David

£97

includes taxes & fees

29 Sept - 30 Sept

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 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.

8. Cambria Hotel & Suites - White Plains Downtown

10.2 mi from Pleasant Square

Aylissia

£193

includes taxes & fees

22 Oct - 23 Oct

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 lounge with leather sofas, a patterned rug, and red pendant lights.

9. Hotel Nyack, a JdV by Hyatt Hotel

5.9 mi from Pleasant Square

Jessica

£140

includes taxes & fees

26 Oct - 27 Oct

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

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

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.

10. Hampton Inn White Plains/Tarrytown

7.4 mi from Pleasant Square

Kenjay

£124

includes taxes & fees

12 Oct - 13 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 bed, a desk with a chair, a TV, and artwork on the walls.

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

11. SpringHill Suites by Marriott Tarrytown Westchester County

6.9 mi from Pleasant Square

ERIC

£134

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

A restaurant with a counter, stools, and a menu board.

12. West Gate Inn Nyack

5.9 mi from Pleasant Square

Wendell

£88

includes taxes & fees

6 Oct - 7 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.

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

13. Residence Inn Orangeburg

9.5 mi from Pleasant Square

Jessica

£135

includes taxes & fees

25 Oct - 26 Oct

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

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.

A coffee station with multiple coffee dispensers, a hot water station, and various coffee products on shelves.

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

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

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

15. Tarrytown House Estate

7.8 mi from Pleasant Square

RAMESH

£156

includes taxes & fees

4 Oct - 5 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.

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

16. Sonesta White Plains Downtown

10.5 mi from Pleasant Square

Tamara

£188

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.

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

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.

17. HYATT house White Plains

12.2 mi from Pleasant Square

Charles

£175

includes taxes & fees

22 Oct - 23 Oct

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.

18. Courtyard by Marriott Tarrytown Westchester County

6.8 mi from Pleasant Square

Syble

£155

includes taxes & fees

18 Oct - 19 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 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 gym with exercise equipment, large windows, and a wooden reception desk.

19. 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 hotel room with a bed, a desk, a chair, a TV, and a lamp.

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

20. Sonesta Simply Suites Nanuet

9.4 mi from Pleasant Square

Theresa

£103

includes taxes & fees

26 Oct - 27 Oct

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Compare popular hotels close to Pleasant Square

Property	Property class	Guest rating
Windrose On Hudson	8.6 Excellent 246 reviews	View
Baymont by Wyndham White Plains - Elmsford	8.4 Very good 1,868 reviews	View
DoubleTree by Hilton Hotel Nanuet	9.0 Wonderful 1,196 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 1,006 reviews	View

Top Pleasant Square Hotel Reviews

Motto By Hilton New York City Times Square

10/10 Excellent

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Hotel Edison Times Square

10/10 Excellent

"We love the staff, the lobby, the little events, how close it is to theaters, Friedman’s, & more! Very cosmopolitan!"

Pod Times Square

8/10 Good

"It was good for a one night stay."

Ameritania Hotel at Times Square

8/10 Good

"Clean and well-located, with very helpful staff. Quite comfortable!"

Night Hotel Broadway

10/10 Excellent

"Staff was great room was slightly nasty but not unbearable I would go and stay again for a last minute change greatful just wish was more clean but the staff was awesome and the cleaning ladies were amazing they help as much as they possibly can I just think it’s an old outdated place and needs a lil makeover!"

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

10/10 Excellent

"staff was awesome helped us out several times i was impressed with the front desk and other workers, much thanks to you all!"

Nap York Central Park Sleep Station

10/10 Excellent

"Great location Helpful staff Easy check-in/out Perfect for solo travel"

Pod 51

10/10 Excellent

"Great, clean all around budget hotel"

Radio Hotel

10/10 Excellent

"Clean rooms, drink vouchers can be used for coffee and snacks, the coffee and expresso wasn't good though. Very loud events in courtyard until 12am. Music was too loud to sleep."

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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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. Baymont by Wyndham White Plains - Elmsford

3. DoubleTree by Hilton Hotel Nanuet

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

5. Hotel MTK Mount Kisco

6. Element by Marriott Spring Valley

7. Ardsley Acres Hotel Westchester

8. Cambria Hotel & Suites - White Plains Downtown

9. Hotel Nyack, a JdV by Hyatt Hotel

10. Hampton Inn White Plains/Tarrytown

11. SpringHill Suites by Marriott Tarrytown Westchester County

12. West Gate Inn Nyack

13. Residence Inn Orangeburg

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

15. Tarrytown House Estate

16. Sonesta White Plains Downtown

17. HYATT house White Plains

18. Courtyard by Marriott Tarrytown Westchester County

19. Sheraton Tarrytown Hotel

20. Sonesta Simply Suites Nanuet

Compare popular hotels close to Pleasant Square

Top Pleasant Square Hotel Reviews

Motto By Hilton New York City Times Square

Hotel Edison Times Square

Pod Times Square

Ameritania Hotel at Times Square

Night Hotel Broadway

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

Nap York Central Park Sleep Station

Pod 51

Radio 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