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 stone fireplace with a fire, surrounded by outdoor seating.

A spacious indoor area with large windows, modern furniture, and a view of a landscaped outdoor area.

A modern interior with seating areas, tables, and artwork on the walls.

1. Windrose On Hudson

3.1 km from Pleasant Square

Rachel

Rp3.267.721

Rp3.639.489 total

includes taxes & fees

27 Sept - 28 Sept

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.

2. Cambria Hotel & Suites - White Plains Downtown

16.5 km from Pleasant Square

Matthew

Rp3.577.675

Rp4.091.964 total

includes taxes & fees

27 Sept - 28 Sept

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.

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

8.5 km from Pleasant Square

Wanda

Rp2.712.094

Rp3.101.958 total

includes taxes & fees

13 Sept - 14 Sept

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.

A spacious lobby with seating areas, a reception desk, and a large plant.

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

4. HYATT house White Plains

19.6 km from Pleasant Square

Lynn

Rp3.434.145

Rp3.927.804 total

includes taxes & fees

20 Sept - 21 Sept

A hotel room with a wooden headboard, a bedside table with a lamp, and a bed with white bedding and pillows.

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.

A reception area with a wooden reception desk, a bulletin board with various items, and an exit sign.

5. Ardsley Acres Hotel Westchester

17.1 km from Pleasant Square

Albert

Rp1.970.495

Rp2.254.032 total

includes taxes & fees

17 Sept - 18 Sept

A spacious lobby with a reception desk, sofas, and a coffee table. There are multiple seating areas and a large window providing natural light.

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.

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

6. Sheraton Tarrytown Hotel

11.4 km from Pleasant Square

Desorene

Rp2.933.858

Rp3.355.602 total

includes taxes & fees

20 Sept - 21 Sept

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 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.

7. Baymont by Wyndham White Plains - Elmsford

10.9 km from Pleasant Square

Ebony

Rp2.222.328

Rp2.541.787 total

includes taxes & fees

20 Sept - 21 Sept

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.

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.

8. Element by Marriott Spring Valley

14.8 km from Pleasant Square

Yocheved

Rp2.359.874

Rp2.746.304 total

includes taxes & fees

27 Sept - 28 Sept

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

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

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

A modern building with a glass facade, surrounded by a landscaped garden with various plants and a classical-style urn.

9. West Gate Inn Nyack

9.6 km from Pleasant Square

Marcelo

Rp1.743.313

Rp1.993.917 total

includes taxes & fees

13 Sept - 14 Sept

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

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 modern building with large glass windows, a brick facade, and a curved section.

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

10. DoubleTree by Hilton Hotel Nanuet

13.8 km from Pleasant Square

Linda

Rp2.151.712

Rp2.504.056 total

includes taxes & fees

27 Sept - 28 Sept

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 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.

11. Sonesta Simply Suites Nanuet

15.1 km from Pleasant Square

EDWARD

Rp1.806.639

Rp2.102.475 total

includes taxes & fees

20 Sept - 21 Sept

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.

12. Days Inn by Wyndham Elmsford / White Plains

12.4 km from Pleasant Square

Frankie

Rp1.870.510

Rp2.200.810 total

includes taxes & fees

20 Sept - 21 Sept

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 gym with treadmills, elliptical machines, and weightlifting equipment.

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

13. Hampton Inn White Plains/Tarrytown

12 km from Pleasant Square

Kenjay

Rp2.079.507

Rp2.378.437 total

includes taxes & fees

20 Sept - 21 Sept

A modern hotel lobby with a dining area, seating, and a large window offering a view of greenery.

A coffee shop with a wooden interior, a coffee machine, and various snacks and beverages on display.

A modern hotel reception area with a wooden reception desk, a sign reading "Hilton Honors," and a seating area with a patterned floor.

A bar area with teal chairs, a large TV screen, and shelves with bottles and glasses.

14. Hilton Garden Inn Westchester Dobbs Ferry, NY

17.7 km from Pleasant Square

Jean

Rp2.671.589

Rp3.055.627 total

includes taxes & fees

5 Oct - 6 Oct

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.

15. Hilton Garden Inn Nanuet

15.2 km from Pleasant Square

cole

Rp2.079.507

Rp2.420.027 total

includes taxes & fees

5 Oct - 6 Oct

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

A two-story building with a white exterior, a balcony on the second floor, and a stone foundation.

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.

16. Inn on the Hudson

15.3 km from Pleasant Square

Sean

Rp1.912.623

Rp2.187.584 total

includes taxes & fees

20 Sept - 21 Sept

A multi-story hotel with a central entrance and a covered waiting area.

17. Extended Stay America Suites White Plains Elmsford

12 km from Pleasant Square

Debbie

Rp2.060.311

Rp2.356.528 total

includes taxes & fees

16 Sept - 17 Sept

A kitchen area with a microwave, coffee machine, and a vending machine stocked with snacks.

A modern hotel lobby with a stone wall, a coffee machine, a microwave, and a trash bin.

A self-service coffee station with a microwave, coffee maker, and beverage dispenser.

A clean, well-lit indoor area with a large window offering a view of a parking lot and a building with a red awning.

18. Motel 6 Elmsford, NY - White Plains

12.2 km from Pleasant Square

"The bed was really nice and it was easy to park. The parking lot was very noisy, with people playing music loudly in their cars for hours on end (both at night and in the morning). The room was good, with a nice big desk to get work done, but the floor was dirty and for sure had not been vacuumed/sweeped before we checked in. The shower was a bit of a hazard because the knob got insanely hot once turned on. The AC worked great, but I didn't like that I couldn't change the direction of the...

Estela

Rp1.958.245

Rp2.239.742 total

includes taxes & fees

13 Sept - 14 Sept

A hotel room with two beds, a desk, a TV, and a mirror.

A multi-story brick building with a covered entrance and a parking lot in front.

A sign for Nyack Motor Lodge with blooming trees in the foreground.

19. Tappan Zee Hotel

10.4 km from Pleasant Square

Bayron

Rp1.497.992

Rp1.743.137 total

includes taxes & fees

13 Sept - 14 Sept

A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.

A bathroom with a large mirror, a sink, and a towel rack.

A large, multi-story hotel with a central entrance and a parking lot.

A Quality Inn entrance sign, a stop sign, and a road leading to a building.

20. Quality Inn Spring Valley - Nanuet

15.2 km from Pleasant Square

Aman

Rp1.894.901

Rp2.205.190 total

includes taxes & fees

24 Sept - 25 Sept

View all properties

Compare popular hotels close to Pleasant Square

Property	Property class	Guest rating
Windrose On Hudson	8.6 Excellent 240 reviews	View
Cambria Hotel & Suites - White Plains Downtown	9.4 Exceptional 1,001 reviews	View
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG	9.0 Wonderful 1,002 reviews	View
HYATT house White Plains	8.8 Excellent 1,176 reviews	View
Ardsley Acres Hotel Westchester	8.8 Excellent 1,156 reviews	View

Top Pleasant Square Hotel Reviews

ROW NYC

10/10 Excellent

"Highly recommend - great location in the middle of everything you would want to do"

Night Hotel Broadway

10/10 Excellent

"Awesome hotel. It was very clean and close to the subway so I could get to time square really quick"

Sheraton New York Times Square Hotel

10/10 Excellent

"Convenient location, clean hotel. Starbucks in the lobby."

Pod Times Square

10/10 Excellent

"A wonderful stay"

Hotel Edison Times Square

8/10 Good

"Convenient location"

Harmony Suites

10/10 Excellent

"I came to attend the Chris Brown and Usher concert. Loved the hotel! It reminded me of a coliseum."

Empire Hotel

10/10 Excellent

"The Empire Hotel is a great place to stay. There is a great restaurant to eat at, on the property and several across the street . It’s close to Columbus Circle. It’s also close to hop on hop off bus stops. Close to the zoo and Central Park. And there’s ice cream every couple of feet."

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 46 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 Highbridge Hotel and Night Hotel Broadway.

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

Expedia has 46 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. 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 Merchants Square.

Search Hotels Near Pleasant Square, Ossining

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Our top choices for Pleasant Square hotels

1. Windrose On Hudson

2. Cambria Hotel & Suites - White Plains Downtown

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

4. HYATT house White Plains

5. Ardsley Acres Hotel Westchester

6. Sheraton Tarrytown Hotel

7. Baymont by Wyndham White Plains - Elmsford

8. Element by Marriott Spring Valley

9. West Gate Inn Nyack

10. DoubleTree by Hilton Hotel Nanuet

11. Sonesta Simply Suites Nanuet

12. Days Inn by Wyndham Elmsford / White Plains

13. Hampton Inn White Plains/Tarrytown

14. Hilton Garden Inn Westchester Dobbs Ferry, NY

15. Hilton Garden Inn Nanuet

16. Inn on the Hudson

17. Extended Stay America Suites White Plains Elmsford

18. Motel 6 Elmsford, NY - White Plains

19. Tappan Zee Hotel

20. Quality Inn Spring Valley - Nanuet

Compare popular hotels close to Pleasant Square

Top Pleasant Square Hotel Reviews

ROW NYC

Night Hotel Broadway

Sheraton New York Times Square Hotel

Pod Times Square

Hotel Edison Times Square

Harmony Suites

Empire 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