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Find hotels near Pleasant Square, Ossining from $95

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Our top choices for Pleasant Square hotels

A two-story house with a gabled roof, a front porch, and a garage.
A modern lounge area with seating, artwork on the walls, and a view of the outdoors.
A building with a brick facade, a covered entrance, and a well-maintained lawn with a bush.
A park with a pond, trees, and a stone wall.

1. Windrose On Hudson

Windrose On Hudson
1.9 mi from Pleasant Square
United States
Rachel
$164 nightly
$183 total
Nov 8 - Nov 9
Total with taxes and fees
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 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

Summer Pool Oasis Custom Bar Arcade Pool Table
0.4 mi from Pleasant Square
$977 nightly
$1,089 total
Nov 3 - Nov 4
Total with taxes and fees
Summer Pool Oasis Custom Bar Arcade Pool Table
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 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.

3. Cambria Hotel & Suites - White Plains Downtown

Cambria Hotel & Suites - White Plains Downtown
10.2 mi from Pleasant Square
United States
Christine
$191 nightly
$219 total
Nov 15 - Nov 16
Total with taxes and fees
Cambria Hotel & Suites - White Plains Downtown
A modern hotel lobby with a kitchen area, seating arrangements, and large windows offering a view of the outdoors.
A modern hotel lobby with a seating area, a kitchen, and a bar.
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.

4. Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford
6.7 mi from Pleasant Square
United States
Amanda
$133 nightly
$153 total
Nov 23 - Nov 24
Total with taxes and fees
Baymont by Wyndham White Plains - Elmsford
A checkered floor, a potted plant, and two metal ladders in a room with large windows.
A restaurant with a counter, stools, and a menu board.
A hotel lobby with a sofa, armchairs, a glass table, and lamps.
A modern building with a glass facade, surrounded by a landscaped garden with various plants and a classical-style urn.

5. West Gate Inn Nyack

West Gate Inn Nyack
5.9 mi from Pleasant Square
United States
Stuart
$97 nightly
$111 total
Nov 22 - Nov 23
Total with taxes and fees
West Gate Inn Nyack
A hotel room with a wooden headboard, a bedside table with a lamp, and a bed with white bedding and pillows.
A café with a counter, coffee machines, a microwave, and a trash can.
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.

6. Ardsley Acres Hotel Westchester

Ardsley Acres Hotel Westchester
10.6 mi from Pleasant Square
United States
Wendell
$117 nightly
$134 total
Nov 24 - Nov 25
Total with taxes and fees
Ardsley Acres Hotel Westchester
An outdoor seating area with modern furniture, a fire pit, and ambient lighting.
A hotel entrance with a glass door, a blue-lit entrance, and a skylight above.
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.
An indoor swimming pool with clear water, surrounded by lounge chairs and a seating area.

7. Sonesta White Plains Downtown

Sonesta White Plains Downtown
10.5 mi from Pleasant Square
United States
Andrew
$178 nightly
$204 total
Nov 22 - Nov 23
Total with taxes and fees
Sonesta White Plains Downtown
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.

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

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
5.3 mi from Pleasant Square
United States
Tammy
$138 nightly
$158 total
Nov 15 - Nov 16
Total with taxes and fees
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
A modern hotel lobby with a dining area, seating, and a large window offering a view of greenery.
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.
A coffee shop with a wooden interior, a coffee machine, and various snacks and beverages on display.

9. Hilton Garden Inn Westchester Dobbs Ferry, NY

Hilton Garden Inn Westchester Dobbs Ferry, NY
11 mi from Pleasant Square
United States
Mustafa
$135 nightly
$155 total
Nov 1 - Nov 2
Total with taxes and fees
Hilton Garden Inn Westchester Dobbs Ferry, NY
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.

10. Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown
7.4 mi from Pleasant Square
United States
Robin
$113 nightly
$129 total
Nov 1 - Nov 2
Total with taxes and fees
Hampton Inn White Plains/Tarrytown
A spacious lounge area with comfortable seating, a bar with a well-stocked shelf, and a modern ceiling design.
A multi-story hotel with a prominent 'Hyatt House' sign, surrounded by well-maintained lawns and trees.
An outdoor patio area with a fire pit, sofas, and umbrellas.
A spacious lobby with seating areas, a reception desk, and a large plant.

11. HYATT house White Plains

HYATT house White Plains
12.2 mi from Pleasant Square
United States
Laura Rebeca
$178 nightly
$203 total
Nov 8 - Nov 9
Total with taxes and fees
HYATT house White Plains
A large building with a fountain in the center surrounded by a circular flower bed.
A fountain with multiple tiers, benches, and a building with a distinctive architectural style and purple flowering vines.
A large, multi-story hotel with a symmetrical facade, multiple windows, and a central entrance with a portico.
A spacious room with large windows, ceiling fans, and a skylight.

12. Hilton Pearl River

Hilton Pearl River
10.8 mi from Pleasant Square
United States
Solomon
$206 nightly
$229 total
Oct 28 - Oct 29
Total with taxes and fees
Hilton Pearl River
A modern high-rise hotel with a curved facade, multiple floors, and a well-lit entrance.
A modern hotel room with a dining area, kitchenette, and a TV.
A modern kitchen with a central island, built-in appliances, and a breakfast bar.
A modern lounge area with sofas, armchairs, a coffee table, and a fireplace.

13. Residence Inn by Marriott White Plains Westchester County

Residence Inn by Marriott White Plains Westchester County
10 mi from Pleasant Square
United States
Cheryl Eileen Anderson
$192 nightly
$220 total
Nov 22 - Nov 23
Total with taxes and fees
Residence Inn by Marriott White Plains Westchester County
A breakfast area with multiple tables and chairs, a kitchen area with appliances, and a sign for Daybreak Breakfast.
A hotel room with a bed, a desk, and a chair. There are two framed pictures on the wall.
A Days Inn lobby with a stone accent wall, a reception desk, and a sign indicating check-in times.
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
7.7 mi from Pleasant Square
United States
Frankie
$119 nightly
$136 total
Nov 1 - Nov 2
Total with taxes and fees
Days Inn by Wyndham Elmsford / White Plains
A modern hotel entrance with a glass door, a car parked outside, and a well-lit pathway leading to the entrance.
A modern lounge area with sofas, armchairs, and a bar.
A modern hotel room with a flat-screen TV, a sofa, a round coffee table, a bed, and a small side table.
A spa room with a massage table, a circular hot tub, and candles.

15. The Opus Westchester, Autograph Collection

The Opus Westchester, Autograph Collection
10.2 mi from Pleasant Square
United States
patricia
$329 nightly
$376 total
Oct 31 - Nov 1
Total with taxes and fees
The Opus Westchester, Autograph Collection
A hotel entrance with a sign reading "SONESTA Simply Suites".
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.
A covered outdoor area with a wooden deck, metal chairs, a round table, and hanging flower baskets.

16. Sonesta Simply Suites Nanuet

Sonesta Simply Suites Nanuet
9.4 mi from Pleasant Square
United States
Susan
$111 nightly
$129 total
Nov 1 - Nov 2
Total with taxes and fees
Sonesta Simply Suites Nanuet
A hotel room with two beds, a desk, a TV, and a mirror.
Two vending machines, one with a Coca-Cola logo and the other with a variety of snacks.
A sign for Nyack Motor Lodge with blooming trees in the foreground.
A spacious lobby with a seating area, a coffee station, and a staircase leading to an upper floor.

17. Tappan Zee Hotel

Tappan Zee Hotel
6.5 mi from Pleasant Square
United States
Kristal
$82 nightly
$95 total
Oct 25 - Oct 26
Total with taxes and fees
Tappan Zee Hotel
A stone building with a tower, surrounded by a garden with large rocks and various plants.
A stone fire pit with flames, surrounded by benches and a building with large windows in the background.
A dining area with large windows, wooden tables, and chairs.
A room with wooden rocking chairs, a coffee maker, and a view of trees through large windows.

18. The Abbey Inn & Spa

The Abbey Inn & Spa
9.7 mi from Pleasant Square
United States
Lina
$369 nightly
$422 total
Nov 24 - Nov 25
Total with taxes and fees
The Abbey Inn & Spa
A kitchen area with a microwave, coffee machine, and a vending machine stocked with snacks.
A hotel room with a bed, bedside tables, a desk, and a chair.
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.

19. Motel 6 Elmsford, NY - White Plains

Motel 6 Elmsford, NY - White Plains
7.6 mi from Pleasant Square
United States
Janice
$103 nightly
$117 total
Oct 27 - Oct 28
Total with taxes and fees
Motel 6 Elmsford, NY - White Plains
Room
Lobby
Breakfast area
A multi-story hotel with a central entrance and a covered waiting area.

20. Extended Stay America Suites White Plains Elmsford

Extended Stay America Suites White Plains Elmsford
7.5 mi from Pleasant Square
United States
Moeti
$139 nightly
$159 total
Nov 2 - Nov 3
Total with taxes and fees
Extended Stay America Suites White Plains Elmsford
View all properties

Top Pleasant Square Hotel Reviews

Hyatt Regency Times Square

Hyatt Regency Times Square

10/10 Excellent
"Staff was excelent"
linda 4-night trip
Posted 1 hour ago
Hyatt Regency Times Square
Night Hotel Broadway

Night Hotel Broadway

8/10 Good
"Not what I'm used to, but for the price and the convenient location it's a good place."
Michael 2-night trip
Posted 5 hours ago
Night Hotel Broadway
Empire Hotel

Empire Hotel

10/10 Excellent
"Stayed with our family of 4. Truly a great experience!"
Kayla 3-night trip
Posted 9 hours ago
Empire Hotel
Hotel Edison Times Square

Hotel Edison Times Square

10/10 Excellent
"El hotel es muy limpio, con un servicio y seguridad excelente. Llevo 3 años reservando mi estadía. Se lo recomiendo. 10/10"
Gretna 4-night trip
Posted 11 hours ago
Hotel Edison Times Square
Park Central Hotel New York

Park Central Hotel New York

8/10 Good
"Clean room, nice bar with lots of seating, jazz music at night. Coffee shop very convenient. Staff not very helpful when trying to get the TV channel changed for a college football game on Saturday. Great location."
Nanci 4-night trip
Posted 17 hours ago
Park Central Hotel New York
Pod 51

Pod 51

8/10 Good
"If you don't mind a small space, this is priced within a tight budget. Very clean and well-maintained."
James 4-night trip
Posted 18 hours ago
Pod 51
Hotel Belleclaire Central Park, a Small Luxury Hotel

Hotel Belleclaire Central Park, a Small Luxury Hotel

8/10 Good
"Clean, spare rooms. Comfortable beds. Breakfast coupons at bakery are great. Drinks in the bar crazy expensive. Great location with lots of restaurants and shopping, Lincoln center walkable."
Maureen 4-night trip
Posted 18 hours ago
Hotel Belleclaire Central Park, a Small Luxury Hotel
Harmony Suites

Harmony Suites

8/10 Good
"The hotel was clean and the room was very spacious. The king bed was very soft and bathroom was clean. The hotel is at a good stop where everything is very accessible."
Naima 2-night trip
Posted 20 hours ago
Harmony Suites

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 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.
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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.
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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.
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.
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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.
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. 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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