Ossining Pleasant Square Hotels

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Check prices for these dates

Tonight
24 Feb - 25 Feb
Tomorrow
25 Feb - 26 Feb
This weekend
27 Feb - 1 Mar
Next weekend
6 Mar - 8 Mar

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Guest rating
Guest rating
Star rating

Our top choices for Pleasant Square hotels

Restaurant

Windrose On Hudson

Windrose On Hudson
3.0 star property
3.1 km from Pleasant Square
8.2 out of 10, Very good, (114 reviews)
"Great staff"
United States
Timothy
The price is HK$1,343
HK$1,496 total
includes taxes & fees
1 Mar - 2 Mar
Windrose On Hudson
Exterior

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
9.0 out of 10, Wonderful, (994 reviews)
"great stay"
United States
Janet
The price is HK$994
HK$1,137 total
includes taxes & fees
17 Mar - 18 Mar
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
Restaurant

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)
"I loved the hotel and its decor and ambience. I would definitely recommend the hotel and I will be staying there again !!!"
United States
Carmen
The price is HK$1,055
HK$1,418 total
includes taxes & fees
2 Mar - 3 Mar
Hotel Nyack, a JdV by Hyatt Hotel
Free daily self-service breakfast

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, (1,574 reviews)
"Clean, comfortable bed and great breakfast!!"
United States
Jennifer
The price is HK$1,056
HK$1,208 total
includes taxes & fees
2 Mar - 3 Mar
Baymont by Wyndham White Plains - Elmsford
Aerial view

Sleepy Hollow Hotel

Sleepy Hollow Hotel
3.5 star property
11.3 km from Pleasant Square
6.8 out of 10, (1,005 reviews)
"Overall the staff was great and the rooms were nice!"
United States
Ashley
The price is HK$1,007
HK$1,152 total
includes taxes & fees
4 Mar - 5 Mar
Sleepy Hollow Hotel
Interior entrance

West Gate Inn Nyack

West Gate Inn Nyack
3.0 star property
9.6 km from Pleasant Square
7.4 out of 10, Good, (1,233 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
Property amenity

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, (1,000 reviews)
"Rooms very clean and staffs we're courteous. "
United States
Sonya
The price is HK$1,188
HK$1,359 total
includes taxes & fees
5 Mar - 6 Mar
Courtyard by Marriott Tarrytown Westchester County
Terrace/patio

Westchester Marriott

Westchester Marriott
4.5 star property
11.7 km from Pleasant Square
8.8 out of 10, Excellent, (482 reviews)
"Friendly staff and the check in and out process was quick. My husband and I stay here several times a year. We are never disappointed. "
United States
Donna
The price is HK$1,454
HK$1,662 total
includes taxes & fees
5 Mar - 6 Mar
Westchester Marriott
Exterior

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, (1,003 reviews)
"Clean and quiet - breakfast had a variety of great options!"
United States
Joann
The price is HK$1,189
HK$1,359 total
includes taxes & fees
8 Mar - 9 Mar
SpringHill Suites by Marriott Tarrytown Westchester County
Indoor pool, open 8:30 AM to 9:30 PM, pool loungers

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, (1,078 reviews)
"Clean room, helpful staff and good bar/restaurant "
United States
Stephen
The price is HK$827
HK$962 total
includes taxes & fees
22 Mar - 23 Mar
DoubleTree by Hilton Hotel Nanuet
Free daily on-the-go breakfast

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 HK$677
HK$809 total
includes taxes & fees
2 Mar - 3 Mar
FairBridge Inn Express Nyack
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
2.5 star property
14.4 km from Pleasant Square
9.2 out of 10, Wonderful, (1,004 reviews)
"Very comfortable beds,clean and breakfast was great."
United States
Dawn
The price is HK$901
HK$1,030 total
includes taxes & fees
15 Mar - 16 Mar
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
3.0 star property
12 km from Pleasant Square
8.0 out of 10, Very good, (1,370 reviews)
"Place is clean and the breakfast is good "
United States
Antonio
The price is HK$987
HK$1,129 total
includes taxes & fees
19 Mar - 20 Mar
Hampton Inn White Plains/Tarrytown
Exterior

Tarrytown House Estate

Tarrytown House Estate
3.5 star property
12.5 km from Pleasant Square
8.2 out of 10, Very good, (1,013 reviews)
"It was a perfect short stay there"
United States
Carl
The price is HK$970
HK$1,305 total
includes taxes & fees
24 Mar - 25 Mar
Tarrytown House Estate
Lobby sitting area

Tappan Zee Hotel

Tappan Zee Hotel
2.0 star property
10.4 km from Pleasant Square
6.4 out of 10, (653 reviews)
"Clean room very quiet"
United States
Kayla
Tappan Zee Hotel
Lobby lounge

Sheraton Tarrytown Hotel

Sheraton Tarrytown Hotel
3.5 star property
11.4 km from Pleasant Square
8.4 out of 10, Very good, (1,002 reviews)
"great comfortable stay !"
United States
Niesha
The price is HK$1,057
HK$1,209 total
includes taxes & fees
8 Mar - 9 Mar
Sheraton Tarrytown Hotel
Interior entrance

Hotel MTK Mount Kisco

Hotel MTK Mount Kisco
3.0 star property
13.2 km from Pleasant Square
8.6 out of 10, Excellent, (1,003 reviews)
"Great hotel. The town is nice. "
United States
Eric
The price is HK$1,083
HK$1,239 total
includes taxes & fees
8 Mar - 9 Mar
Hotel MTK Mount Kisco
Vending machine

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, (948 reviews)
"Easy parking, lots of restaurants near, dogs are welcome, beds are old, "
United States
kathy
The price is HK$774
HK$885 total
includes taxes & fees
8 Mar - 9 Mar
Motel 6 Elmsford, NY - White Plains
Restaurant

Armoni Inn & Suites

Armoni Inn & Suites
3.5 star property
14.6 km from Pleasant Square
6.0 out of 10, (2,161 reviews)
"Reasonable for price, and quiet"
United States
Andrew
The price is HK$478
HK$533 total
includes taxes & fees
1 Mar - 2 Mar
Armoni Inn & Suites
Exterior

Sonesta Simply Suites Nanuet

Sonesta Simply Suites Nanuet
2.5 star property
15.1 km from Pleasant Square
8.4 out of 10, Very good, (1,106 reviews)
"Staff was nice, bed comfortable. "
United States
Misty
The price is HK$719
HK$836 total
includes taxes & fees
26 Feb - 27 Feb
Sonesta Simply Suites Nanuet
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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Compare popular hotels close to Pleasant Square

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
Restaurant
Windrose On Hudson
3.0 star property
8.2
Very good
114 reviews
View
Exterior
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
2.5 star property
9.0
Wonderful
994 reviews
View
Restaurant
Hotel Nyack, a JdV by Hyatt Hotel
4.0 star property
8.6
Excellent
1,005 reviews
View
Free daily self-service breakfast
Baymont by Wyndham White Plains - Elmsford
2.5 star property
8.2
Very good
1,574 reviews
View
Aerial view
Sleepy Hollow Hotel
3.5 star property
6.8
1,005 reviews
View

Top Pleasant Square Hotel Reviews

Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

10/10 Excellent
"The location the employees the cleaners. Well done. We will start staying here. Thk uuu. 5 stars "
Allyson 3-night trip
Posted 1 day ago
Sheraton New York Times Square 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 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 50 hotels and other accommodations within a few miles for a convenient home base.
Where is the best place to stay close to Pleasant Square?
Ly New York Hotel is one of the top choices for your stay based on our traveller data, and this hotel offers free parking and a 24-hour fitness centre. You'll find it 26.2 mi (42.1 km) from Pleasant Square. Other good options around the area include Hotel Belleclaire and Sheraton New York Times Square Hotel.
How many hotels should I expect to find near Pleasant Square?
Expedia has 50 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.