The Best Hotels Closest to 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.

1. Windrose On Hudson

3.1 km from Pleasant Square

Rachel

₩253,758

₩282,628 total

includes taxes & fees

Sep 27 - Sep 28

A spacious living room with a large window, a ceiling fan, a dining area with a table and chairs, and a staircase leading to an upper level.

A large, two-story house with a prominent front entrance, multiple windows, and a driveway.

A modern living room with a sectional sofa, a coffee table, and large windows offering a view of trees.

A swimming pool with lounge chairs and a wooden deck, surrounded by trees and a building with a sloped roof.

2. Summer Pool Oasis Custom Bar Arcade Pool Table

0.7 km from Pleasant Square

₩855,352

₩1,600,909 total

includes taxes & fees

Sep 2 - Sep 3

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

A Holiday Inn Express & Suites building with a covered entrance, multiple windows, and a landscaped area with plants and a fire hydrant.

An indoor swimming pool with clear depth markers, lounge chairs, and safety signs.

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

14.4 km from Pleasant Square

David

₩207,827

₩237,707 total

includes taxes & fees

Sep 13 - Sep 14

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

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.

A hotel corridor with a patterned carpet, a railing, and a reception desk with a glass partition.

4. Baymont by Wyndham White Plains - Elmsford

10.9 km from Pleasant Square

Ebony

₩184,831

₩211,399 total

includes taxes & fees

Sep 13 - Sep 14

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

A café with a counter, coffee machines, a microwave, and a trash can.

5. Ardsley Acres Hotel Westchester

17.1 km from Pleasant Square

Nicole

₩165,384

₩189,167 total

includes taxes & fees

Oct 1 - Oct 2

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.

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.

6. Hotel MTK Mount Kisco

13.2 km from Pleasant Square

Victoria

₩223,165

₩255,245 total

includes taxes & fees

Sep 8 - Sep 9

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.

7. Cambria Hotel & Suites - White Plains Downtown

16.5 km from Pleasant Square

Matthew

₩261,485

₩299,074 total

includes taxes & fees

Sep 27 - Sep 28

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.

8. Hotel Nyack, a JdV by Hyatt Hotel

9.5 km from Pleasant Square

Ruby

₩172,675

₩234,782 total

includes taxes & fees

Sep 13 - Sep 14

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.

9. West Gate Inn Nyack

9.6 km from Pleasant Square

James

₩135,379

₩154,840 total

includes taxes & fees

Sep 20 - Sep 21

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

10. DoubleTree by Hilton Hotel Nanuet

13.8 km from Pleasant Square

Linda

₩162,518

₩189,130 total

includes taxes & fees

Sep 20 - Sep 21

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

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.

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

11. HYATT house White Plains

19.6 km from Pleasant Square

Charles

₩254,374

₩290,940 total

includes taxes & fees

Sep 13 - Sep 14

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

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

12. Hampton Inn White Plains/Tarrytown

12 km from Pleasant Square

Joseph

₩154,758

₩177,003 total

includes taxes & fees

Sep 27 - Sep 28

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 compact kitchen with a dining area, a flat-screen TV, a microwave, a coffee maker, and a refrigerator.

13. Sonesta Simply Suites Nanuet

15.1 km from Pleasant Square

EDWARD

₩144,419

₩168,067 total

includes taxes & fees

Sep 20 - Sep 21

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.

14. Hilton Garden Inn Westchester Dobbs Ferry, NY

17.7 km from Pleasant Square

Vanessa

₩178,308

₩203,942 total

includes taxes & fees

Sep 13 - Sep 14

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

A Days Inn with a brick facade, a covered walkway, and a parking lot.

15. Days Inn by Wyndham Elmsford / White Plains

12.4 km from Pleasant Square

Jennifer

₩148,975

₩175,208 total

includes taxes & fees

Sep 27 - Sep 28

A spacious interior with a high ceiling, stone walls, and modern furniture.

A spacious corridor with stone walls, large windows, and a central chandelier.

An indoor swimming pool with a wooden ceiling and brick walls.

A spacious room with a stone fireplace, white sofas, and a large window offering a view of the outdoors.

16. Sleepy Hollow Hotel, a Dolce by Wyndham

11.3 km from Pleasant Square

Johnny

₩187,361

₩214,293 total

includes taxes & fees

Sep 28 - Sep 29

A large building with a fountain in the center surrounded by a circular flower bed.

A spacious room with large windows, ceiling fans, and a skylight.

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

A large, multi-story hotel with a symmetrical facade, multiple windows, and a central entrance with a portico.

17. Hilton Pearl River

17.4 km from Pleasant Square

Anrthony

₩313,290

₩348,927 total

includes taxes & fees

Sep 10 - Sep 11

A snow-covered outdoor area with a stone wall, a metal fence, and a lamp post.

A view from a window overlooking a lake with trees and hills in the distance.

A hotel room with two beds, a large window with curtains, a door, and a small table with a lamp.

A view from a covered porch overlooking a lake, with a white fence and trees in the foreground.

18. Inn on the Hudson

15.3 km from Pleasant Square

Sean

₩149,068

₩170,498 total

includes taxes & fees

Sep 6 - Sep 7

A spacious lobby with a central reception desk, two large potted plants, and a patterned rug.

A bar area with a white countertop, bar stools, a television, and various bottles.

A modern hotel lobby with a fireplace, seating area, and a bar cart with bottles.

A Hilton Garden Inn with a clear sky, a covered entrance, and multiple flags.

19. Hilton Garden Inn Nanuet

15.2 km from Pleasant Square

cole

₩151,981

₩176,869 total

includes taxes & fees

Sep 14 - Sep 15

20. Extended Stay America Suites White Plains Elmsford

12 km from Pleasant Square

Shondrea

₩162,389

₩185,734 total

includes taxes & fees

Sep 8 - Sep 9

View all properties

Top Pleasant Square Hotel Reviews

Hotel Edison Times Square

10/10 Excellent

"quick and easy check in, breakfast coupons and they got us a taxi immediately when we had to leave early in the morning"

Park Central Hotel New York

10/10 Excellent

"The restaurant/lounging area was ideal for us. John was excellent bartender and very helpful with information about the city. The staff was friendly from the moment we arrived until the moment we left."

Sheraton New York Times Square Hotel

8/10 Good

"Overall, great stay! The elevator bank to our floor was out of service for much of our stay. Waited a minimum of 15 minutes to get to our room each time we went back up. Most comfortable hotel bed Ive ever slept in!"

OYO Times Square

10/10 Excellent

"Great location for the price It’s all you need to be in Times Square the staff was so amazing we had a great trip!"

Night Hotel Broadway

10/10 Excellent

"Staff"

Harmony Suites

10/10 Excellent

"The parking was easy, the front desk staff was very responsive to all the requested needs. The room was clean , with great space. The overall stay was safe and quiet. Outstanding experience. Will definitely come back again."

Empire Hotel

10/10 Excellent

"Great location! Near central park. Well mantained property. They give water bottles. Theres a few restaurant nearby. Near the bus stop and metro station. You can also leave the luggage after check out. Will be back!"

Highbridge Hotel

8/10 Good

"Was a good stay"

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

10/10 Excellent

"A little smaller room, but was a very nice room and was quiet."

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 quaint 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 family-friendly 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 family-friendly 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

Sing Sing Correctional Facility

After visiting Sing Sing Correctional Facility, make a plan to see the other sights and activities in Ossining. Amble around this family-friendly 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 47 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 Highbridge Hotel and Night Hotel Broadway.

How many hotels can I expect to find near Pleasant Square?

Expedia has 47 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.

Where can I learn more about changing or cancelling my trip in the area near Pleasant Square?

For additional details about updating your stay near Pleasant Square or cancelling it, go to https://www.expedia.com/service/.

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. Sing Sing Correctional Facility, Van Cortlandt Manor, and Sleepy Hollow Cemetery 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.

Find hotels near Pleasant Square, Ossining from ₩154,840

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. Summer Pool Oasis Custom Bar Arcade Pool Table

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

4. Baymont by Wyndham White Plains - Elmsford

5. Ardsley Acres Hotel Westchester

6. Hotel MTK Mount Kisco

7. Cambria Hotel & Suites - White Plains Downtown

8. Hotel Nyack, a JdV by Hyatt Hotel

9. West Gate Inn Nyack

10. DoubleTree by Hilton Hotel Nanuet

11. HYATT house White Plains

12. Hampton Inn White Plains/Tarrytown

13. Sonesta Simply Suites Nanuet

14. Hilton Garden Inn Westchester Dobbs Ferry, NY

15. Days Inn by Wyndham Elmsford / White Plains

16. Sleepy Hollow Hotel, a Dolce by Wyndham

17. Hilton Pearl River

18. Inn on the Hudson

19. Hilton Garden Inn Nanuet

20. Extended Stay America Suites White Plains Elmsford

Top Pleasant Square Hotel Reviews

Hotel Edison Times Square

Park Central Hotel New York

Sheraton New York Times Square Hotel

OYO Times Square

Night Hotel Broadway

Harmony Suites

Empire Hotel

Highbridge Hotel

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

Sing Sing Correctional Facility

Frequently asked questions