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Jan 12 - Jan 13
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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, (107 reviews)
"Clean room, staff were very welcoming"
United States
Semaj
The price is ₩294,288
₩327,763 total
includes taxes & fees
Jan 25 - Jan 26
Windrose On Hudson
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, (975 reviews)
"great stay"
United States
Janet
The price is ₩195,521
₩223,628 total
includes taxes & fees
Jan 22 - Jan 23
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
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, (1,488 reviews)
"Enjoyed the free breakfast and the workout room had options; great location for access into city"
United States
Kathleen Elizabeth
The price is ₩158,751
₩181,572 total
includes taxes & fees
Jan 15 - Jan 16
Baymont by Wyndham White Plains - Elmsford
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, (1,005 reviews)
"Clean room , staff and amenities were all great"
United States
Elzie
The price is ₩196,980
₩264,822 total
includes taxes & fees
Jan 19 - Jan 20
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, (1,003 reviews)
"Staff is very friendly and helpful. The restaurant in the lobby is very convenient. Room is spacious. Had a great stay here."
United States
Guoxiu
The price is ₩208,653
₩238,648 total
includes taxes & fees
Jan 25 - Jan 26
Courtyard by Marriott Tarrytown Westchester County
Terrace/patio
Westchester Marriott

Westchester Marriott

Westchester Marriott
4.5 star property
11.7 km from Pleasant Square
8.8 out of 10, Excellent, (464 reviews)
"Comfy bed and nice breakfast!"
United States
Ignacio
The price is ₩230,685
₩263,845 total
includes taxes & fees
Jan 22 - Jan 23
Westchester Marriott
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
11.2 km from Pleasant Square
8.4 out of 10, Very Good, (1,008 reviews)
"Room was clean and great size."
Canada
Robert
The price is ₩209,601
₩239,730 total
includes taxes & fees
Jan 18 - Jan 19
SpringHill Suites by Marriott Tarrytown Westchester County
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, (1,001 reviews)
"Overall the staff was great and the rooms were nice!"
United States
Ashley
The price is ₩177,486
₩203,020 total
includes taxes & fees
Jan 28 - Jan 29
Sleepy Hollow Hotel
Restaurant
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, (1,004 reviews)
"Good for a short stay! "
United States
NUTAN
The price is ₩136,792
₩161,562 total
includes taxes & fees
Jan 23 - Jan 24
Days Inn by Wyndham Elmsford / White Plains
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, (1,210 reviews)
"Good price...Clean, friendly staff, comfy rooms and it has breakfast and plenty of parking space, definitely coming back! "
United States
Israhel
West Gate Inn Nyack
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, (1,027 reviews)
"Good food hot tub great bed was wonderful area beautiful staff so nice"
United States
vontisha
The price is ₩135,201
₩157,341 total
includes taxes & fees
Feb 1 - Feb 2
DoubleTree by Hilton Hotel Nanuet
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, (1,004 reviews)
"great comfortable stay !"
United States
Niesha
The price is ₩197,199
₩225,547 total
includes taxes & fees
Jan 25 - Jan 26
Sheraton Tarrytown Hotel
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, (941 reviews)
"Easy parking, lots of restaurants near, dogs are welcome, beds are old, "
United States
kathy
The price is ₩144,452
₩165,215 total
includes taxes & fees
Jan 13 - Jan 14
Motel 6 Elmsford, NY - White Plains
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, (1,001 reviews)
"Very comfortable beds,clean and breakfast was great."
United States
Dawn
The price is ₩167,798
₩191,919 total
includes taxes & fees
Jan 25 - Jan 26
Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG
Free daily buffet breakfast
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, (1,342 reviews)
"Room was clean, staff was friendly and the hotel was conveniently located to my destination."
United States
melissa
The price is ₩178,274
₩203,900 total
includes taxes & fees
Jan 18 - Jan 19
Hampton Inn White Plains/Tarrytown
Free daily on-the-go breakfast
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, (1,002 reviews)
"The staff was really friendly and the place is clean"
Canada
Sara
The price is ₩130,226
₩155,457 total
includes taxes & fees
Jan 18 - Jan 19
FairBridge Inn Express Nyack
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, (649 reviews)
"Clean room very quiet"
United States
Kayla
Tappan Zee Hotel
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, (1,006 reviews)
"Hotel was beautiful and clean "
United States
April
The price is ₩185,290
₩248,403 total
includes taxes & fees
Jan 14 - Jan 15
Tarrytown House Estate
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, (2,167 reviews)
"Easy access to highway and to local dining options."
United States
Sarah
Armoni Inn & Suites
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, (1,004 reviews)
"Great hotel. The town is nice. "
United States
Eric
The price is ₩202,203
₩231,270 total
includes taxes & fees
Feb 8 - Feb 9
Hotel MTK Mount Kisco
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

Night Hotel Broadway

Night Hotel Broadway

10/10 Excellent
"Great service they let us check in early 🙏🙏🙏"
Eric 3-night trip
Posted 10 hours ago
Night Hotel Broadway

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 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 38 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 38 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. 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 Teatown Lake Reservation.