Hotels near Pleasant Square

Start date: Check-in selected.
To Date
End date: Check-out

  • 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
Dec 24 - Dec 25
Tomorrow
Dec 25 - Dec 26
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Pleasant Square hotels

Restaurant
Windrose On Hudson

Windrose On Hudson

Windrose On Hudson
3.0 star property
3.1 km from Pleasant Square
8.2 out of 10, Very Good, (104)
"Clean room, staff were very welcoming"
United States
Semaj
The price is P10,892
P12,131 total
includes taxes & fees
Jan 10 - Jan 11, 2026
Windrose On Hudson
5 bedrooms
Foliage at Westchester Manor - Near Sleepy Hollow

Foliage at Westchester Manor - Near Sleepy Hollow

Foliage at Westchester Manor - Near Sleepy Hollow
2.0 star property
0.7 km from Pleasant Square
The price is P22,499
P52,711 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Foliage at Westchester Manor - Near Sleepy Hollow
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 P8,339
P9,537 total
includes taxes & fees
Jan 9 - Jan 10, 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, (1000)
"Nice clean place.. friendly staff .. fireplace in lobby perfect for chillin "
United States
Adam
The price is P9,454
P10,813 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Courtyard by Marriott Tarrytown Westchester County
Interior
Cambria Hotel & Suites - White Plains Downtown

Cambria Hotel & Suites - White Plains Downtown

Cambria Hotel & Suites - White Plains Downtown
3.5 star property
16.5 km from Pleasant Square
9.4 out of 10, Exceptional, (1002)
"Clean room, excellent guest services!"
United States
Patti
The price is P13,440
P15,372 total
includes taxes & fees
Dec 25 - Dec 26
Cambria Hotel & Suites - White Plains Downtown
Indoor pool, open 8:30 AM to 9:30 PM, sun loungers
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
9.0 out of 10, Wonderful, (1011)
"Clean room, friendly staff, good breakfast"
United States
Zuriber
The price is P5,742
P6,682 total
includes taxes & fees
Jan 4 - Jan 5, 2026
DoubleTree by Hilton Hotel Nanuet
Restaurant
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, (1003)
"Room was clean, staff was pleasant, hotel overall was great"
United States
Cara
The price is P7,927
P10,658 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Hotel Nyack, a JdV by Hyatt Hotel
Terrace/patio
Westchester Marriott

Westchester Marriott

Westchester Marriott
4.5 star property
11.7 km from Pleasant Square
8.8 out of 10, Excellent, (451)
"Comfy bed and nice breakfast!"
United States
Ignacio
The price is P10,475
P11,980 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Westchester Marriott
Exterior
The Abbey Inn & Spa

The Abbey Inn & Spa

The Abbey Inn & Spa
4.0 star property
15.6 km from Pleasant Square
9.2 out of 10, Wonderful, (231)
"We had a very short stay but what i can say is that rooms were extremely clean, the staff was beyond courteous extremely helpful restaurants was not only beautiful but food services once again amazing.. We look foward to coming back for a longer stay and try the spa out as well.."
United States
Paul
The price is P16,592
P21,664 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Abbey Inn & Spa
Exterior
The Opus Westchester, Autograph Collection

The Opus Westchester, Autograph Collection

The Opus Westchester, Autograph Collection
5.0 star property
16.5 km from Pleasant Square
9.2 out of 10, Wonderful, (528)
"our room was very clean on beds very comfortable staff friendly, breakfast wonderful"
United States
Susan
The price is P17,558
P22,097 total
includes taxes & fees
Dec 26 - Dec 27
The Opus Westchester, Autograph Collection
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, (1003)
"Room was clean and great size."
Canada
Robert
The price is P8,935
P10,219 total
includes taxes & fees
Jan 1 - Jan 2, 2026
SpringHill Suites by Marriott Tarrytown Westchester County
Lobby
Element Spring Valley

Element Spring Valley

Element Spring Valley
3.0 star property
14.8 km from Pleasant Square
8.8 out of 10, Excellent, (439)
"This was our third time staying there and it continues to be great!"
United States
Debra
The price is P7,869
P9,157 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Element Spring Valley
Free daily self-serve 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)
"I highly recommend this hotel. "
United States
Leigh
The price is P7,179
P8,211 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG
View from property
Residence Inn Orangeburg

Residence Inn Orangeburg

Residence Inn Orangeburg
3.0 star property
15.4 km from Pleasant Square
8.8 out of 10, Excellent, (1003)
"We’ve stayed here multiple times and we’ve enjoyed each time. The breakfast options are varied, perfect for the whole family. The staff are courteous. The rooms are always clean. "
United States
ERIN
The price is P8,421
P9,379 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Residence Inn Orangeburg
Lobby lounge
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 P7,953
P9,096 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Sheraton Tarrytown Hotel
Free daily self-serve 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, (1461)
"Breakfast was already but the staff are so ghetto hotel was clean also the pool "
United States
Shantay
The price is P6,953
P7,952 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Baymont by Wyndham White Plains - Elmsford
Exterior
Sonesta White Plains Downtown

Sonesta White Plains Downtown

Sonesta White Plains Downtown
4.0 star property
16.9 km from Pleasant Square
8.8 out of 10, Excellent, (1165)
"Clean rooms, great location and friendly staff"
United States
Gerardo
The price is P9,336
P12,630 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Sonesta White Plains Downtown
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, (1000)
"Excellent hotel. "
United States
Samuel
The price is P8,619
P9,858 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Hotel MTK Mount Kisco
Exterior
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, (1010)
"It was a lovely stay. The room was really comfortable and quiet "
United States
Kathy
The price is P8,784
P11,518 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Tarrytown House Estate
Exterior
Residence Inn by Marriott White Plains Westchester County

Residence Inn by Marriott White Plains Westchester County

Residence Inn by Marriott White Plains Westchester County
3.0 star property
16.1 km from Pleasant Square
8.6 out of 10, Excellent, (654)
"Staff very helpful "
United States
Bianca
The price is P10,746
P12,291 total
includes taxes & fees
Jan 16 - Jan 17, 2026
Residence Inn by Marriott White Plains Westchester County
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.
View all properties

Top Pleasant Square Hotel Reviews

Ameritania Hotel at Times Square

Ameritania Hotel at Times Square

10/10 Excellent
"Staff continues to be welcoming and accommodating. Rooms are clean and spacious by NYC standards.Great vibe overall. Safe neighborhood and excellent dining choices nearby. "
Mary Lynne 1-night trip
Posted 15 hours ago
Ameritania Hotel at Times Square

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 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

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 34 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 (35.4 km) from Pleasant Square. Other good options around the area include Night Hotel Broadway and Sheraton New York Times Square Hotel.
How many hotels can I expect to find near Pleasant Square?
Expedia has 34 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. 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.