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Our top choices for Pleasant Square hotels

A spacious indoor area with a long row of chairs, a blue sofa, and a wooden table.
A two-story house with a red door, white siding, and a brick pathway leading to the entrance.
A conference room with multiple tables and chairs, a projector, and a presentation screen.
A hotel room with a bed, a desk, a chair, and a view of the outside.

1. Windrose On Hudson

Windrose On Hudson
3.1 km from Pleasant Square
United States
Rachel
CA $214
CA $238 total
includes taxes & fees
Nov 8 - Nov 9
Windrose On Hudson
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 traditional Tudor-style house with a spacious front yard, a stone wall, and a well-maintained garden.
A large, two-story house with a prominent front entrance, multiple windows, and a driveway.
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

Summer Pool Oasis Custom Bar Arcade Pool Table
0.7 km from Pleasant Square
CA $714
CA $1,464 total
includes taxes & fees
Nov 3 - Nov 4
Summer Pool Oasis Custom Bar Arcade Pool Table
A spacious lobby with a modern design, featuring a seating area with sofas and armchairs, a decorative wall panel, and a large window providing natural light.
A modern restaurant interior with a bar area, seating, and a dessert display.
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 lobby with a reception desk, seating area, and a large window allowing natural light.

3. DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
13.8 km from Pleasant Square
United States
Linda
CA $191
CA $222 total
includes taxes & fees
Nov 1 - Nov 2
DoubleTree by Hilton Hotel Nanuet
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 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.

4. Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford
10.9 km from Pleasant Square
United States
Amanda
CA $194
CA $222 total
includes taxes & fees
Nov 1 - Nov 2
Baymont by Wyndham White Plains - Elmsford
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 multi-story hotel with a modern design, featuring a prominent logo on the facade.
An outdoor patio with stone walls, a fire pit, and seating.

5. Element by Marriott Spring Valley

Element by Marriott Spring Valley
14.8 km from Pleasant Square
United States
Danielle
CA $202
CA $235 total
includes taxes & fees
Nov 1 - Nov 2
Element by Marriott Spring Valley
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 reception area with a wooden reception desk, a bulletin board with various items, and an exit sign.

6. Ardsley Acres Hotel Westchester

Ardsley Acres Hotel Westchester
17.1 km from Pleasant Square
United States
David
CA $176
CA $202 total
includes taxes & fees
Nov 16 - Nov 17
Ardsley Acres Hotel Westchester
A hotel with a modern facade, a prominent signage for SpringHill Suites Marriott, and a covered entrance area with seating.
A bar area with a long counter, multiple chairs, and a television mounted on the wall.
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 buffet setup with various food items, a coffee station, and seating area.

7. SpringHill Suites by Marriott Tarrytown Westchester County

SpringHill Suites by Marriott Tarrytown Westchester County
11.2 km from Pleasant Square
United States
Warren
CA $220
CA $251 total
includes taxes & fees
Nov 12 - Nov 13
SpringHill Suites by Marriott Tarrytown Westchester County
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 lobby with teal patterned chairs, a fireplace, and a flat-screen TV mounted above it.

8. Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown
12 km from Pleasant Square
United States
Robin
CA $172
CA $197 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn White Plains/Tarrytown
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 courtyard with a fire pit, outdoor seating, and modern apartment buildings.
A modern cafe with multiple seating options including tables, chairs, and sofas.

9. Courtyard by Marriott Tarrytown Westchester County

Courtyard by Marriott Tarrytown Westchester County
10.9 km from Pleasant Square
United States
Syble
CA $214
CA $245 total
includes taxes & fees
Nov 1 - Nov 2
Courtyard by Marriott Tarrytown Westchester County
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 modern breakfast bar with a variety of food options, including cereal and hot food. There are signs indicating breakfast and hot food availability.

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

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
8.5 km from Pleasant Square
United States
Tammy
CA $182
CA $208 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
A modern lobby with seating areas, a fireplace, and a flat-screen TV mounted on the wall.
A modern hotel lobby with a large sofa, dining area, and large windows offering city views.
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 lobby with a reception desk, seating area, and a decorative wall.

11. Cambria Hotel & Suites - White Plains Downtown

Cambria Hotel & Suites - White Plains Downtown
16.5 km from Pleasant Square
United States
Christine
CA $270
CA $309 total
includes taxes & fees
Nov 15 - Nov 16
Cambria Hotel & Suites - White Plains Downtown
A spacious lobby with a red sofa, green armchairs, a fireplace, and a staircase leading to an upper level.
A spacious lobby with a red sofa set, a fireplace, and a staircase leading to an upper level.
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.

12. Hotel MTK Mount Kisco

Hotel MTK Mount Kisco
13.2 km from Pleasant Square
United States
eric w
CA $207
CA $237 total
includes taxes & fees
Nov 16 - Nov 17
Hotel MTK Mount Kisco
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.

13. Sheraton Tarrytown Hotel

Sheraton Tarrytown Hotel
11.4 km from Pleasant Square
United States
Kerry-Anna
CA $202
CA $231 total
includes taxes & fees
Nov 12 - Nov 13
Sheraton Tarrytown Hotel
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.
A modern building with a glass facade, a red door, and a staircase leading to the entrance.

14. Hotel Nyack, a JdV by Hyatt Hotel

Hotel Nyack, a JdV by Hyatt Hotel
9.5 km from Pleasant Square
United States
Liana
CA $150
CA $209 total
includes taxes & fees
Nov 17 - Nov 18
Hotel Nyack, a JdV by Hyatt Hotel
A hotel patio with outdoor seating, a fire pit, and a covered area with glass doors.
A modern lobby with a fireplace, bookshelves, and a seating area.
Lobby
An indoor swimming pool with a 'NO DIVING' sign, lounge chairs, and a lifeguard chair.

15. Residence Inn Orangeburg

Residence Inn Orangeburg
15.4 km from Pleasant Square
United States
KAREN
CA $196
CA $218 total
includes taxes & fees
Nov 8 - Nov 9
Residence Inn Orangeburg
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 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.

16. Hilton Garden Inn Westchester Dobbs Ferry, NY

Hilton Garden Inn Westchester Dobbs Ferry, NY
17.7 km from Pleasant Square
United States
Mustafa
CA $191
CA $218 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Westchester Dobbs Ferry, NY
A breakfast area with multiple tables and chairs, a kitchen area with appliances, and a sign for Daybreak Breakfast.
A gym with treadmills, exercise balls, and a yoga mat.
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.

17. Days Inn by Wyndham Elmsford / White Plains

Days Inn by Wyndham Elmsford / White Plains
12.4 km from Pleasant Square
United States
Frankie
CA $162
CA $185 total
includes taxes & fees
Nov 10 - Nov 11
Days Inn by Wyndham Elmsford / White Plains
A hotel room with a wooden desk, a green chair, a gray sofa, a kitchenette, and a door with a sign.
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.
A Hampton Inn hotel with a clear sky and sunset.

18. Hampton Inn Nanuet

Hampton Inn Nanuet
15.1 km from Pleasant Square
United States
Leonard
CA $172
CA $201 total
includes taxes & fees
Oct 26 - Oct 27
Hampton Inn Nanuet
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.

19. HYATT house White Plains

HYATT house White Plains
19.6 km from Pleasant Square
United States
Laura Rebeca
CA $251
CA $287 total
includes taxes & fees
Nov 8 - Nov 9
HYATT house White Plains
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 coffee station with multiple coffee dispensers, a hot water station, and various coffee products on shelves.

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

Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG
14.4 km from Pleasant Square
United States
Edwin
CA $196
CA $224 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG
View all properties

Top Pleasant Square Hotel Reviews

ROW NYC

ROW NYC

8/10 Good
"Fantastic location. Clean room. I booked one night and extended my stay and the staff member the first night put me in a room with a lower rate, but did not inform me. When I extended my stay, the second staff member offered me a discount based on the room I was in, which was an unexpected happy surprise."
Aisha 1-night trip
Posted 1 hour ago
ROW NYC
Park Lane New York

Park Lane New York

10/10 Excellent
"Room was good, great view of the city, and next to central park"
Amey 3-night trip
Posted 9 hours ago
Park Lane New York
Harmony Suites

Harmony Suites

8/10 Good
"Although the building didn't feel particularly new, it was well-maintained, and the room was spacious and comfortable. There was a large window facing the area next to the entrance, yet I didn't notice any noise. I had high hopes for breakfast, but it was disappointing to find items like the bacon served cold."
Serina 1-night trip
Posted 11 hours ago
Harmony Suites
Lotte New York Palace

Lotte New York Palace

10/10 Excellent
"I wouldn't stay anywhere else in New York! The location is perfect since I can easily walk to the theater, but don't have to stay in Times Square. (Love the theater; don't love navigating Times Square.) On this trip, special shoutout to Stacy, who greeted me and my daughter so cordially when we arrived late Sunday evening (Oct. 11th) and then the next day helped us with a logistical problem. Can't wait to visit again."
Donna 3-night trip
Posted 13 hours ago
Lotte New York Palace

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.
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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.
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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 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 quaint 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 quaint area, or check out 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.
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 36 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 Night Hotel Broadway and Hotel Belleclaire Central Park, a Small Luxury Hotel.
How many hotels can I expect to find near Pleasant Square?
Expedia has 36 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.
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 Louis Engel Waterfront Park.

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