Top Hotels Near Pleasant Square in Ossining from NZ$175

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12 Dec - 13 Dec
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Our top choices for Pleasant Square hotels

Exterior
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
2.5 star property
8.5 km from Pleasant Square
8.8 out of 10, Excellent, (952)
"The woman who was in the breakfast room she is lovely and so helpful!"
United States
Suzanne
The price is NZ$293
includes taxes & fees
3 Jan - 4 Jan 2026
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
Lobby
Hotel Nyack, a JdV by Hyatt Hotel

Hotel Nyack, a JdV by Hyatt Hotel

Hotel Nyack, a JdV by Hyatt Hotel
4.0 star property
9.5 km from Pleasant Square
8.6 out of 10, Excellent, (1004)
"Room was clean, staff was pleasant, hotel overall was great"
United States
Cara
The price is NZ$279
includes taxes & fees
21 Dec - 22 Dec
Hotel Nyack, a JdV by Hyatt Hotel
Property amenity
Courtyard by Marriott Tarrytown Westchester County

Courtyard by Marriott Tarrytown Westchester County

Courtyard by Marriott Tarrytown Westchester County
3.0 star property
10.9 km from Pleasant Square
9.0 out of 10, Wonderful, (1003)
"Nice clean place.. friendly staff .. fireplace in lobby perfect for chillin "
United States
Adam
The price is NZ$299
includes taxes & fees
11 Jan - 12 Jan 2026
Courtyard by Marriott Tarrytown Westchester County
Free daily self-service breakfast
Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford
2.5 star property
10.9 km from Pleasant Square
8.2 out of 10, Very good, (1458)
"Great experience can’t wait to come back "
United States
Marvin
The price is NZ$243
includes taxes & fees
1 Jan - 2 Jan 2026
Baymont by Wyndham White Plains - Elmsford
Reception
Westchester Marriott

Westchester Marriott

Westchester Marriott
4.5 star property
11.7 km from Pleasant Square
8.8 out of 10, Excellent, (440)
"Comfy bed and nice breakfast!"
United States
Ignacio
The price is NZ$366
includes taxes & fees
20 Dec - 21 Dec
Westchester Marriott
Lobby
Days Inn by Wyndham Elmsford / White Plains

Days Inn by Wyndham Elmsford / White Plains

Days Inn by Wyndham Elmsford / White Plains
2.0 star property
12.4 km from Pleasant Square
6.8 out of 10, (1003)
"Stuff at the front desk was great"
United States
Bernardo
The price is NZ$203
includes taxes & fees
21 Dec - 22 Dec
Days Inn by Wyndham Elmsford / White Plains
View from property
Inn on the Hudson

Inn on the Hudson

Inn on the Hudson
2.0 star property
15.3 km from Pleasant Square
6.8 out of 10, (1001)
"Always a pleasant place "
United States
Abner
The price is NZ$175
includes taxes & fees
14 Dec - 15 Dec
Inn on the Hudson
Interior entrance
West Gate Inn Nyack

West Gate Inn Nyack

West Gate Inn Nyack
3.0 star property
9.6 km from Pleasant Square
7.4 out of 10, Good, (1180)
"Always a great stay when I visit the area. "
United States
Joseph
The price is NZ$208
includes taxes & fees
26 Dec - 27 Dec
West Gate Inn Nyack
Exterior
SpringHill Suites by Marriott Tarrytown Westchester County

SpringHill Suites by Marriott Tarrytown Westchester County

SpringHill Suites by Marriott Tarrytown Westchester County
3.0 star property
11.1 km from Pleasant Square
8.4 out of 10, Very good, (1001)
"The staff that work the front desk are excellent and so professional. It is wonderful that the property changes the breakfast every day and that they do not have the same breakfast every day."
United States
Sonja
The price is NZ$300
includes taxes & fees
18 Dec - 19 Dec
SpringHill Suites by Marriott Tarrytown Westchester County
Lobby
Motel 6 Elmsford, NY - White Plains

Motel 6 Elmsford, NY - White Plains

Motel 6 Elmsford, NY - White Plains
2.0 star property
12.2 km from Pleasant Square
6.6 out of 10, (922)
"Very affordable compared to surrounding hotels"
United States
CRAIG A
The price is NZ$195
includes taxes & fees
14 Dec - 15 Dec
Motel 6 Elmsford, NY - White Plains
Basic Triple Room | Interior
Tappan Zee Hotel

Tappan Zee Hotel

Tappan Zee Hotel
2.0 star property
10.4 km from Pleasant Square
6.4 out of 10, (646)
"We had a good stay, but the shower was messed up. Other than that, it was fine."
United States
Kizuwanda
Tappan Zee Hotel
Exterior
Sheraton Tarrytown Hotel

Sheraton Tarrytown Hotel

Sheraton Tarrytown Hotel
3.5 star property
11.4 km from Pleasant Square
8.4 out of 10, Very good, (1002)
"great comfortable stay !"
United States
Niesha
The price is NZ$283
includes taxes & fees
4 Jan - 5 Jan 2026
Sheraton Tarrytown Hotel
Reception
FairBridge Inn Express Nyack

FairBridge Inn Express Nyack

FairBridge Inn Express Nyack
2.0 star property
9.8 km from Pleasant Square
7.6 out of 10, Good, (1000)
"Clean room, friendly staff, good location "
Canada
Andrew
The price is NZ$180
includes taxes & fees
5 Jan - 6 Jan 2026
FairBridge Inn Express Nyack
Lobby
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
4.0 star property
13.8 km from Pleasant Square
8.8 out of 10, Excellent, (1001)
"Great staff, clean and the pool was awesome! "
Canada
Aleah
The price is NZ$195
includes taxes & fees
4 Jan - 5 Jan 2026
DoubleTree by Hilton Hotel Nanuet
Indoor pool, seasonal outdoor pool
Tarrytown House Estate

Tarrytown House Estate

Tarrytown House Estate
3.5 star property
12.5 km from Pleasant Square
8.2 out of 10, Very good, (1000)
"Beautiful property highly recommend if in the area goose feather is a great on site resteraunt as well"
United States
Erek
The price is NZ$345
includes taxes & fees
22 Dec - 23 Dec
Tarrytown House Estate
Meeting facility
Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown
3.0 star property
12 km from Pleasant Square
8.0 out of 10, Very good, (1296)
"Clean rooms, good parking & nice staff."
United States
Shakeia
The price is NZ$238
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn White Plains/Tarrytown
Free daily self-service breakfast
Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG

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

Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG
2.5 star property
14.4 km from Pleasant Square
9.2 out of 10, Wonderful, (1001)
"Beautiful hotel, great breakfast!"
United States
Elaine
The price is NZ$234
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG
Interior entrance
Hotel MTK Mount Kisco

Hotel MTK Mount Kisco

Hotel MTK Mount Kisco
3.0 star property
13.2 km from Pleasant Square
8.4 out of 10, Very good, (1001)
"Excellent hotel. "
United States
Samuel
The price is NZ$289
includes taxes & fees
1 Jan - 2 Jan 2026
Hotel MTK Mount Kisco
Premium bedding, desk, blackout curtains, free WiFi
Quality Inn Spring Valley - Nanuet

Quality Inn Spring Valley - Nanuet

Quality Inn Spring Valley - Nanuet
2.5 star property
15.2 km from Pleasant Square
6.2 out of 10, (1001)
"easy to navigate"
United States
Francis
The price is NZ$194
includes taxes & fees
5 Jan - 6 Jan 2026
Quality Inn Spring Valley - Nanuet
Restaurant
Armoni Inn & Suites

Armoni Inn & Suites

Armoni Inn & Suites
3.5 star property
14.6 km from Pleasant Square
6.0 out of 10, (2171)
"Easy access to highway and to local dining options."
United States
Sarah
Armoni Inn & Suites
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Pleasant Square Hotel Reviews

Empire Hotel

Empire Hotel

10/10 Excellent
"Excelent Staff"
Christian 3-night trip
Posted 10 hours ago
Empire Hotel

Hotels near other Pleasant Square attractions

Merchants Square

Explore the great outdoors at Merchants Square, a lovely green space in Ossining. Stroll along the riverfront or attend a sporting event in this family-friendly area.
See properties

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.
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 traveller data, and this hotel offers a restaurant and a 24-hour fitness centre. You'll find it 22 mi (35.4 km) from Pleasant Square. Other good options around the area include Night Hotel Broadway and Sheraton New York Times Square Hotel.
How many hotels should I expect to find near Pleasant Square?
Expedia has 36 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 Croton Landing Park.

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