Default HTG hotel image

Find hotels near Pleasant Square, Ossining from CA $158

  • 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
Oct 12 - Oct 13
Tomorrow
Oct 13 - Oct 14
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Filter by

Star rating

Guest rating

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 gym with treadmills, a red carpet, and exercise equipment.

1. Windrose On Hudson

Windrose On Hudson
3.1 km from Pleasant Square
United States
Rachel
CA $215
CA $240 total
includes taxes & fees
Nov 8 - Nov 9
Windrose On Hudson
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 building with large glass windows, a brick facade, and a curved section.
A modern restaurant interior with a bar area, seating, and a dessert display.
A hotel lobby with a reception desk, seating area, and a large window allowing natural light.

2. DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
13.8 km from Pleasant Square
United States
Linda
CA $193
CA $224 total
includes taxes & fees
Oct 27 - Oct 28
DoubleTree by Hilton Hotel Nanuet
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.

3. Sheraton Tarrytown Hotel

Sheraton Tarrytown Hotel
11.4 km from Pleasant Square
United States
Andrew
CA $204
CA $234 total
includes taxes & fees
Nov 1 - Nov 2
Sheraton Tarrytown Hotel
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 restaurant with a counter, stools, and a menu board.

4. West Gate Inn Nyack

West Gate Inn Nyack
9.6 km from Pleasant Square
United States
Stuart
CA $138
CA $158 total
includes taxes & fees
Nov 9 - Nov 10
West Gate Inn Nyack
An outdoor seating area with wicker chairs and tables, surrounded by greenery and a modern lamp structure.
A formal dining setup with multiple tables, each set with clear glassware, plates, and cutlery.
Lounge
A bar area with a long counter, multiple shelves with bottles, and several bar stools.

5. Westchester Marriott

Westchester Marriott
11.7 km from Pleasant Square
United States
Robert
CA $265
CA $304 total
includes taxes & fees
Nov 1 - Nov 2
Westchester Marriott
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 modern hotel lobby with a seating area, a kitchen, and a bar.

6. Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford
10.9 km from Pleasant Square
United States
Heather
CA $193
CA $220 total
includes taxes & fees
Nov 2 - Nov 3
Baymont by Wyndham White Plains - Elmsford
A modern kitchen with a large island, bar stools, a flat-screen TV, and a stone backsplash.
A lobby with teal patterned chairs, a fireplace, and a flat-screen TV mounted above it.
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.

7. Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown
12 km from Pleasant Square
United States
James
CA $176
CA $202 total
includes taxes & fees
Nov 9 - Nov 10
Hampton Inn White Plains/Tarrytown
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 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.

8. Ardsley Acres Hotel Westchester

Ardsley Acres Hotel Westchester
17.1 km from Pleasant Square
United States
David
CA $171
CA $196 total
includes taxes & fees
Nov 11 - Nov 12
Ardsley Acres Hotel Westchester
A modern hotel corridor with a blue wall featuring geometric shapes, a white bench, and an elevator.
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.

9. 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
Maureen
CA $238
CA $272 total
includes taxes & fees
Nov 12 - Nov 13
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
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.
A modern kitchen with a central island, bar stools, wooden cabinets, and pendant lighting.

10. Element by Marriott Spring Valley

Element by Marriott Spring Valley
14.8 km from Pleasant Square
United States
Danielle
CA $204
CA $237 total
includes taxes & fees
Oct 26 - Oct 27
Element by Marriott Spring Valley
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

SpringHill Suites by Marriott Tarrytown Westchester County
11.2 km from Pleasant Square
United States
Warren
CA $222
CA $254 total
includes taxes & fees
Oct 18 - Oct 19
SpringHill Suites by Marriott Tarrytown Westchester County
A modern kitchen with a central island, bar stools, a fireplace, and a contemporary pendant light.
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.
A courtyard with a fire pit, outdoor seating, and modern apartment buildings.

12. Courtyard by Marriott Tarrytown Westchester County

Courtyard by Marriott Tarrytown Westchester County
10.9 km from Pleasant Square
United States
Justine
CA $230
CA $263 total
includes taxes & fees
Nov 1 - Nov 2
Courtyard by Marriott Tarrytown Westchester County
A modern bar area with a bar counter, multiple stools, and a seating area with a sofa and chairs.
Room
A modern building with a glass facade, a red door, and a staircase leading to the entrance.
A modern dining area with a wooden table, cushioned seating, pendant lighting, and a large window offering a view of the outdoors.

13. Hotel Nyack, a JdV by Hyatt Hotel

Hotel Nyack, a JdV by Hyatt Hotel
9.5 km from Pleasant Square
United States
Jessica
CA $159
CA $220 total
includes taxes & fees
Nov 1 - Nov 2
Hotel Nyack, a JdV by Hyatt Hotel
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 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.

14. Days Inn by Wyndham Elmsford / White Plains

Days Inn by Wyndham Elmsford / White Plains
12.4 km from Pleasant Square
United States
Frankie
CA $164
CA $192 total
includes taxes & fees
Oct 25 - Oct 26
Days Inn by Wyndham Elmsford / White Plains
A modern lobby with seating areas, a fireplace, and a flat-screen TV mounted on the wall.
A modern bar area with a bar counter, seating, and a colorful mural.
A modern lobby with a reception desk, seating area, and a decorative wall.
A modern hotel lobby with a large sofa, dining area, and large windows offering city views.

15. Cambria Hotel & Suites - White Plains Downtown

Cambria Hotel & Suites - White Plains Downtown
16.5 km from Pleasant Square
United States
Gina
CA $273
CA $312 total
includes taxes & fees
Nov 8 - Nov 9
Cambria Hotel & Suites - White Plains Downtown
A hotel entrance with a sign reading "SONESTA Simply Suites".
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.
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.

16. Sonesta Simply Suites Nanuet

Sonesta Simply Suites Nanuet
15.1 km from Pleasant Square
United States
Susan
CA $161
CA $187 total
includes taxes & fees
Oct 18 - Oct 19
Sonesta Simply Suites Nanuet
A hotel room with a wooden desk, a green chair, a gray sofa, a kitchenette, and a door with a sign.
A Hampton Inn hotel with a clear sky and sunset.
A hotel room with a bed, a desk, a chair, a TV, and a painting on the wall.
A modern hotel lobby with a long communal table, seating area, and a kitchenette.

17. Hampton Inn Nanuet

Hampton Inn Nanuet
15.1 km from Pleasant Square
United States
Ildar
CA $163
CA $189 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn Nanuet
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.
A spacious restaurant with high tables and stools, a bar area, and a television screen displaying a sports game.
A spacious lobby with a red sofa set, a fireplace, and a staircase leading to an upper level.

18. Hotel MTK Mount Kisco

Hotel MTK Mount Kisco
13.2 km from Pleasant Square
United States
eric w
CA $221
CA $253 total
includes taxes & fees
Nov 1 - Nov 2
Hotel MTK Mount Kisco
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.

19. 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 $221
CA $253 total
includes taxes & fees
Nov 9 - Nov 10
Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG
An outdoor seating area with modern furniture, a fire pit, and ambient lighting.
An indoor swimming pool with clear water, surrounded by lounge chairs and a seating area.
A modern bar area with a long counter, multiple stools, and a bar stocked with bottles.
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.

20. Sonesta White Plains Downtown

Sonesta White Plains Downtown
17 km from Pleasant Square
United States
Andrew
CA $245
CA $328 total
includes taxes & fees
Nov 8 - Nov 9
Sonesta White Plains Downtown
View all properties

Compare popular hotels close to Pleasant Square

Property
Star rating
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
A spacious indoor area with a long row of chairs, a blue sofa, and a wooden table.
Windrose On Hudson
8.6
Excellent
257 reviews
View
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.
DoubleTree by Hilton Hotel Nanuet
9.0
Wonderful
1,193 reviews
View
A spacious lobby with a reception desk, sofas, and a coffee table. There are multiple seating areas and a large window providing natural light.
Sheraton Tarrytown Hotel
8.4
Very good
1,007 reviews
View
A hotel room with a wooden desk, a green chair, a gray sofa, a kitchenette, and a door with a sign.
Hampton Inn Nanuet
8.2
Very good
1,005 reviews
View
An outdoor seating area with wicker chairs and tables, surrounded by greenery and a modern lamp structure.
Westchester Marriott
9.0
Wonderful
667 reviews
View

Top Pleasant Square Hotel Reviews

ROW NYC

ROW NYC

8/10 Good
"A decent hotel in midtown / Times Square area. Lines for elevators were sometimes long. Lobby has some useful amenities. Rooms small but adequate. Overall, a good stay. Surprisingly quiet for the area, which I liked!"
Nora 2-night trip
Posted 3 hours ago
ROW NYC
Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

10/10 Excellent
"The hotel was nicer than expected, the elevators were great. The full size bed felt on the small side, but the room was great and location was wonderful. Right across the street from a subway station we used frequently. We did have to pay a destination tax which came out to $40 per day, just a heads up,"
Jacquelyn 3-night trip
Posted 4 hours ago
Sheraton New York Times Square Hotel
Empire Hotel

Empire Hotel

10/10 Excellent
"Wonderful central location to Central Park, Broadway, Time Square, and shopping for different budgets. Breakfast, lunch, dinner, and snack spots on location and within a short walk. Beautiful property is clean and well maintained. Friendly and helpful staff. Would highly recommend!"
Stephanie 3-night trip
Posted 5 hours ago
Empire Hotel
Park Lane New York

Park Lane New York

10/10 Excellent
"Easy to find everything was near by. Will definitely be coming back and staying here again. Room was clean and staff was friendly and helpful. The weather was great this time of year for walking."
Nestor 3-night trip
Posted 5 hours ago
Park Lane New York
Harmony Suites

Harmony Suites

10/10 Excellent
"Great property with a bus stop to get you to nyc but the breakfast could use a little work, and some updates but all in all a great place"
Dustin 2-night trip
Posted 8 hours ago
Harmony Suites
Hyatt Regency Times Square

Hyatt Regency Times Square

10/10 Excellent
"Amazing"
Melany 1-night trip
Posted 10 hours ago
Hyatt Regency Times Square
Pod 51

Pod 51

10/10 Excellent
"I love that they let me check in early."
Emil 2-night trip
Posted 12 hours ago
Pod 51

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 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.
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

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.

Explore a world of travel with Expedia