Hotels near Pleasant Square, Ossining

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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 room with multiple foosball tables and people playing.

A spacious dining area with multiple tables and chairs, large windows, and a modern chandelier.

A conference room with a large screen displaying a building image, a whiteboard, and a table with laptops, papers, and coffee cups.

1. Windrose On Hudson

3.1 km from Pleasant Square

Rachel

S$303

includes taxes & fees

27 Sept - 28 Sept

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 sign for Ardsley Acres Hotel Court with a landscaped garden in the background.

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

2. Ardsley Acres Hotel Westchester

17.1 km from Pleasant Square

David

S$163

includes taxes & fees

29 Sept - 30 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 Holiday Inn Express & Suites hotel with a modern design, featuring a covered entrance and American flags.

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

A hotel room with two beds, a blue sofa, a wooden coffee table, and a painting on the wall.

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

8.5 km from Pleasant Square

Wanda

S$249

includes taxes & fees

18 Oct - 19 Oct

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 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.

4. HYATT house White Plains

19.6 km from Pleasant Square

Charles

S$297

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 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.

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

5. Hampton Inn White Plains/Tarrytown

12 km from Pleasant Square

Susan

S$190

includes taxes & fees

1 Oct - 2 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 compact kitchen with a dining area, a flat-screen TV, a microwave, a coffee maker, and a refrigerator.

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

6. Sonesta Simply Suites Nanuet

15.1 km from Pleasant Square

Theresa

S$156

includes taxes & fees

4 Oct - 5 Oct

A breakfast area with multiple tables and chairs, a kitchen area with appliances, and a sign for Daybreak Breakfast.

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

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

A gym with treadmills, exercise balls, and a yoga mat.

7. Days Inn by Wyndham Elmsford / White Plains

12.4 km from Pleasant Square

Frankie

S$168

includes taxes & fees

18 Oct - 19 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.

8. Element by Marriott Spring Valley

14.8 km from Pleasant Square

Michaelle

S$195

includes taxes & fees

4 Oct - 5 Oct

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.

9. Tappan Zee Hotel

10.4 km from Pleasant Square

Salim

S$127

includes taxes & fees

27 Sept - 28 Sept

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

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

A backyard with a swimming pool, lounge chairs, and a small shed.

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

10. Quality Inn Spring Valley - Nanuet

15.2 km from Pleasant Square

Philip

S$161

includes taxes & fees

26 Oct - 27 Oct

A hotel room with a bed, two wall-mounted lamps, a round wooden table with a vase of flowers, and two framed pictures on the wall.

A building with a brown roof, a sign reading "OFFICE", and a parking sign with a 'B' indicating a parking bay.

A bathroom with a freestanding bathtub, a towel, and a window.

A street view with a Budget Motor Inn sign, a building with a beige facade, and a grassy area with a curb.

11. Budget Motor Inn - Stony Point

12.3 km from Pleasant Square

Matt

S$105

includes taxes & fees

26 Oct - 27 Oct

A breakfast buffet with pastries, fruits, and a coffee station.

A modern living room with a large flat-screen TV, a sofa, a coffee table, and a dining area with a glass table.

A modern living room with a sofa, a coffee table, and a TV. There are stairs leading to another room.

A modern living room with a sofa, coffee table, and TV. There is a plant and a window with curtains.

12. 3BR Prime Luxury NY - Free Parking

15.6 km from Pleasant Square

Osmond

S$1,471

includes taxes & fees

10 Oct - 11 Oct

A modern living room with a sectional sofa, a glass coffee table, and a marble rug. There are two wall art pieces and a potted plant.

A modern kitchen with wooden cabinets, a granite countertop, and three bar stools.

A modern living room with a flat-screen TV mounted on a white wall, wooden flooring, and a large abstract rug.

A modern kitchen with a wooden cabinet, a bar stool, and a dining table with white chairs.

13. Luxury NYC Home Game Room Free Parking

13.8 km from Pleasant Square

"After flying in with four of us from Los Angeles on a Red Eye, we had to drive around for 4-5 hours until we were able to check in at 4pm, however after hours of trying to get into the property with no answer on the contact number ,we finally were able to have the local property manager come out and say that the property overbooked and had no room for us. I spent over 2 hours on the phone getting the run around by Expedia with mixed stories of our accommodations. FINALLY with now the story is...

Jorge

S$913

includes taxes & fees

10 Oct - 11 Oct

A modern bedroom with a large bed, a bedside table, a TV, and a window with curtains.

14. Upscale Modern Luxury 3BR Home

17.3 km from Pleasant Square

Russell

S$728

includes taxes & fees

27 Sept - 28 Sept

A modern kitchen with white cabinetry, a stainless steel sink, a built-in washing machine, and a pendant light.

15. Luxury 3BR NY Home with Free Parking

15.8 km from Pleasant Square

keasiah

S$637

includes taxes & fees

10 Oct - 11 Oct

A modern kitchen with stainless steel appliances, white cabinetry, and a wooden floor.

A bed with white bedding and gold and white pillows, a wall-mounted light fixture, and a large green plant.

A potted plant with variegated leaves next to a flat-screen TV mounted on a light-colored wall.

A modern living room with a green sofa, a glass coffee table, a white armchair, and a large flat-screen TV mounted on a light-colored wall.

16. Elegant Hideaway with Free Parking

13.9 km from Pleasant Square

S$452

includes taxes & fees

10 Oct - 11 Oct

A hotel room with a large bed, a sitting area with a chair, a bathroom with a bathtub, and a television on the wall.

A bathroom with a white bathtub, a shower, and a yellow wall.

A Days Inn reception area with a counter, bar stools, and a clock on the wall.

A hotel room with a large bed, a sitting area with a chair, a television, a microwave, and a bathtub.

17. Days Inn by Wyndham Nanuet / Spring Valley

15.4 km from Pleasant Square

Jason L

S$150

includes taxes & fees

26 Oct - 27 Oct

A dining table with a variety of pastries and fruits, a vase with flowers, and a view of a brick wall and greenery outside.

A modern bedroom with a large bed, bedside tables, a potted plant, and a view of the outdoors.

18. Luxury NYC Home with Free Parking for 12

15.6 km from Pleasant Square

Kathleen

S$805

includes taxes & fees

10 Oct - 11 Oct

A modern living room with a white sofa, a glass coffee table, and a flat-screen TV mounted on the wall.

A modern living room with a glass dining table, white sofas, and a flat-screen TV mounted on the wall.

A kitchen with white cabinets, a stove, and a toaster. There are shelves with various food items and kitchen supplies.

A modern bedroom with a large bed, white bedding, and a potted plant.

19. Upscale 3BR NY Home with Free Parking

15.7 km from Pleasant Square

"The property was double booked and they took my money and the code was never received therefore I could not check in to the property. I’m still waiting on a refund of $416.02 . The property should not be listed if people are occupying it. I was distraught when I found out this on my birthday weekend scrambling to find a place to go at almost midnight. This person should be banned from renting out this property so that it doesn’t happen again!"

Nicole

S$697

includes taxes & fees

26 Oct - 27 Oct

A dining table with a glass top, a vase with flowers, and a variety of pastries and fruits.

A neatly arranged bedroom with a large bed, white bedding, a bedside table, and a potted plant.

20. Prime Luxe 3-BR NYC - Free Parking

15.7 km from Pleasant Square

S$960

includes taxes & fees

27 Sept - 28 Sept

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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
Ardsley Acres Hotel Westchester	8.8 Excellent 1,181 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 1,173 reviews	View
Hampton Inn White Plains/Tarrytown	8.0 Very good 1,684 reviews	View

Top Pleasant Square Hotel Reviews

Hotel Edison Times Square

10/10 Excellent

"This hotel was in a perfect position for our 3 nights in NYC. Half a block from the subway and Broadway. The rooms were larger than most in the area and had ever needed including very comfortable beds. Loved the free breakfast. Basic but very well organised and great pastries. The attached restaurant was wonderful with the singing wait staff. A great venue when we just arrived and didn’t want to go any further."

Empire Hotel

10/10 Excellent

"Tiene habitaciones internas y solo ves unos tubos de refrigeracion. Pondria vidrios esmerilados y luces . Son muy chicas. Bien decoradas."

Pod Times Square

10/10 Excellent

"Great location and value."

Ameritania Hotel at Times Square

10/10 Excellent

"."

Warwick New York

10/10 Excellent

"The staff was very helpful and professional. The location was exceptional, with outstanding shopping and Central Park in walking distance. We enjoyed Murals Restaurant for breakfast and Randolph’s is the perfect lounge for an evening cocktail. The atmosphere is very old school NYC. We’ll definitely be back!"

ROW NYC

10/10 Excellent

"The staff were wonderful, especially the front desk staff. The breakfast is very good and the location is super convenient."

Park Lane New York

8/10 Good

"El cuarto cuando llegué tenía bolsas de basura de las personas que estaban antes , los cuartos ya necesitan mantenimiento de pintura y detalles , la ubicación es excelente y el servicio también lo único es que ya es viejo y le falta cariño en detalles"

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.

Hotels near Pleasant Square

Change your mind

Treat yourself

Be picky

Check prices for these dates

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Our top choices for Pleasant Square hotels

1. Windrose On Hudson

2. Ardsley Acres Hotel Westchester

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

4. HYATT house White Plains

5. Hampton Inn White Plains/Tarrytown

6. Sonesta Simply Suites Nanuet

7. Days Inn by Wyndham Elmsford / White Plains

8. Element by Marriott Spring Valley

9. Tappan Zee Hotel

10. Quality Inn Spring Valley - Nanuet

11. Budget Motor Inn - Stony Point

12. 3BR Prime Luxury NY - Free Parking

13. Luxury NYC Home Game Room Free Parking

14. Upscale Modern Luxury 3BR Home

15. Luxury 3BR NY Home with Free Parking

16. Elegant Hideaway with Free Parking

17. Days Inn by Wyndham Nanuet / Spring Valley

18. Luxury NYC Home with Free Parking for 12

19. Upscale 3BR NY Home with Free Parking

20. Prime Luxe 3-BR NYC - Free Parking

Compare popular hotels close to Pleasant Square

Top Pleasant Square Hotel Reviews

Hotel Edison Times Square

Empire Hotel

Pod Times Square

Ameritania Hotel at Times Square

Warwick New York

ROW NYC

Park Lane 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