Hotels near Pleasant Square

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17 Dec - 18 Dec
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18 Dec - 19 Dec
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19 Dec - 21 Dec
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26 Dec - 28 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, (955)
"The rooms are updated and clean The bed had topper and was very comfy Fantastic breakfast available and tasty All cooked in house "
United States
stephen
The price is S$209
includes taxes & fees
9 Jan - 10 Jan, 2026
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
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, (1004)
"Nice clean place.. friendly staff .. fireplace in lobby perfect for chillin "
United States
Adam
The price is S$212
includes taxes & fees
4 Jan - 5 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, (1462)
"The rooms and the hospitality was amazing."
United States
Debra
The price is S$182
includes taxes & fees
4 Jan - 5 Jan, 2026
Baymont by Wyndham White Plains - Elmsford
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, (1000)
"Always a pleasant place "
United States
Abner
The price is S$131
includes taxes & fees
21 Dec - 22 Dec
Inn on the Hudson
Reception
Westchester Marriott

Westchester Marriott

Westchester Marriott
4.5 star property
11.7 km from Pleasant Square
8.8 out of 10, Excellent, (441)
"Comfy bed and nice breakfast!"
United States
Ignacio
The price is S$274
includes taxes & fees
19 Dec - 20 Dec
Westchester Marriott
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, (1000)
"Room was clean, staff was pleasant, hotel overall was great"
United States
Cara
The price is S$222
includes taxes & fees
23 Dec - 24 Dec
Hotel Nyack, a JdV by Hyatt Hotel
Aerial view
Sleepy Hollow Hotel

Sleepy Hollow Hotel

Sleepy Hollow Hotel
3.5 star property
11.3 km from Pleasant Square
6.8 out of 10, (1003)
"excellent place "
United States
Boruch
The price is S$190
includes taxes & fees
28 Dec - 29 Dec
Sleepy Hollow Hotel
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, (1000)
"Stuff at the front desk was great"
United States
Bernardo
The price is S$152
includes taxes & fees
28 Dec - 29 Dec
Days Inn by Wyndham Elmsford / White Plains
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, (1002)
"The hotel did the job. Staff was great and accommodating. It was clean and rooms were nice. "
United States
Alex
The price is S$224
includes taxes & fees
21 Dec - 22 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 S$146
includes taxes & fees
18 Dec - 19 Dec
Motel 6 Elmsford, NY - White Plains
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, (647)
"We had a good stay, but the shower was messed up. Other than that, it was fine."
United States
Kizuwanda
Tappan Zee Hotel
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, (1186)
"Always a great stay when I visit the area. "
United States
Joseph
The price is S$157
includes taxes & fees
26 Dec - 27 Dec
West Gate Inn Nyack
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, (1001)
"great comfortable stay !"
United States
Niesha
The price is S$199
includes taxes & fees
4 Jan - 5 Jan, 2026
Sheraton Tarrytown Hotel
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, (1309)
"Room was clean, staff was friendly and the hotel was conveniently located to my destination."
United States
melissa
The price is S$183
includes taxes & fees
4 Jan - 5 Jan, 2026
Hampton Inn White Plains/Tarrytown
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, (1008)
"Great staff, clean and the pool was awesome! "
Canada
Aleah
The price is S$146
includes taxes & fees
4 Jan - 5 Jan, 2026
DoubleTree by Hilton Hotel Nanuet
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, (1001)
"Clean room, friendly staff, good location "
Canada
Andrew
The price is S$114
includes taxes & fees
8 Jan - 9 Jan, 2026
FairBridge Inn Express Nyack
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, (2164)
"Easy access to highway and to local dining options."
United States
Sarah
Armoni Inn & Suites
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, (1002)
"I highly recommend this hotel. "
United States
Leigh
The price is S$175
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, (1006)
"Its very close to the work location "
United States
John
The price is S$216
includes taxes & fees
1 Jan - 2 Jan, 2026
Hotel MTK Mount Kisco
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, (1003)
"Beautiful property highly recommend if in the area goose feather is a great on site resteraunt as well"
United States
Erek
The price is S$264
includes taxes & fees
4 Jan - 5 Jan, 2026
Tarrytown House Estate
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

The Manhattan Club

The Manhattan Club

10/10 Excellent
"Excellent location, friendly and helpful staff. We love staying at the Manhattan Club!"
Thomas
Posted 14 hours ago
The Manhattan Club

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 35 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 35 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 Rockwood Hall Park.