Ossining Hotel Guide - Pleasant Square hotels in Ossining, United States of America.

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Check prices for these dates

This weekend
29 May - 31 May
Next weekend
5 Jun - 7 Jun

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Our top choices for Pleasant Square hotels

Restaurant

Windrose On Hudson

Windrose On Hudson
3.0 star property
3.1 km from Pleasant Square
8.4 out of 10, Very good, (157 reviews)
"Ev chargers on site. Lovely grounds and facilities. Will definitely stay here next time i am in the area."
United States
Andrew
The price is €155
includes taxes & fees
22 Jun - 23 Jun
Windrose On Hudson
Basic Triple Room | Interior

Tappan Zee Hotel

Tappan Zee Hotel
2.0 star property
10.4 km from Pleasant Square
6.4 out of 10, (665 reviews)
"Stay was smooth. Check in was quick, room was clean. I didn't need any of the amenities as my stay was for brief for a day but all in all it was good."
United States
Karen
The price is €73
includes taxes & fees
3 Jun - 4 Jun
Tappan Zee Hotel
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, (1,001 reviews)
"We had a great stay, the hotel was very clean and the room was spacious. Easy parking and check in. Hotel was in a good location close to dining options."
United States
Casey
The price is €141
includes taxes & fees
31 May - 1 Jun
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
Free daily on-the-go breakfast

FairBridge Inn Express Nyack

FairBridge Inn Express Nyack
2.0 star property
9.8 km from Pleasant Square
7.8 out of 10, Good, (1,001 reviews)
"Awesome lodging experience!"
United States
Suruba
The price is €101
includes taxes & fees
7 Jun - 8 Jun
FairBridge Inn Express Nyack
Interior entrance

West Gate Inn Nyack

West Gate Inn Nyack
3.0 star property
9.6 km from Pleasant Square
7.2 out of 10, Good, (1,306 reviews)
"Breakfast was ok. Rooms were very neat and the staff were awesome."
United States
Edmund
The price is €97
includes taxes & fees
31 May - 1 Jun
West Gate Inn Nyack
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
8.4 out of 10, Very good, (1,696 reviews)
"It was very clean and friendly staff"
United States
Wynona
The price is €132
includes taxes & fees
31 May - 1 Jun
Baymont by Wyndham White Plains - Elmsford
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, (969 reviews)
"Parking good. HVAC good. Bath good. Room floor a little disheveled. Needed more lamps. Very convenient."
United States
Bruce
The price is €114
includes taxes & fees
2 Jun - 3 Jun
Motel 6 Elmsford, NY - White Plains
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, (1,003 reviews)
"Room was nice. Clean and comfortable."
United States
allen
The price is €158
includes taxes & fees
14 Jun - 15 Jun
Sheraton Tarrytown Hotel
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)
"Staff was friendly and helpful, rooms were super clean, hotel stayed for a trip to Tarrytown, New York"
United States
Michael
The price is €175
includes taxes & fees
14 Jun - 15 Jun
Courtyard by Marriott Tarrytown Westchester County
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
8.6 out of 10, Excellent, (1,002 reviews)
"Enjoyed our stay"
United States
Piper
The price is €178
includes taxes & fees
4 Jun - 5 Jun
SpringHill Suites 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, (553 reviews)
"Great stay"
United States
Leneir
The price is €220
includes taxes & fees
28 Jun - 29 Jun
Westchester Marriott
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, (1,138 reviews)
"Convenient location, clean room, staff friendly and helpful."
United States
Thomas
The price is €122
includes taxes & fees
1 Jun - 2 Jun
DoubleTree by Hilton Hotel Nanuet
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, (1,468 reviews)
"Great place have stayed there before"
United States
Waynes
The price is €121
includes taxes & fees
28 Jun - 29 Jun
Hampton Inn White Plains/Tarrytown
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, (1,002 reviews)
"Excellent stay, I always book the MTK when I’m in the area. "
United States
Heidi
The price is €152
includes taxes & fees
29 Jun - 30 Jun
Hotel MTK Mount Kisco
Free daily self-service breakfast

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

Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG
2.5 star property
14.4 km from Pleasant Square
9.2 out of 10, Wonderful, (1,000 reviews)
"Great place to stay. "
United States
Jennifer
The price is €163
includes taxes & fees
7 Jun - 8 Jun
Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG
Exterior

Tarrytown House Estate

Tarrytown House Estate
3.5 star property
12.5 km from Pleasant Square
8.2 out of 10, Very good, (1,094 reviews)
"Great place to stay"
United States
Deanna
The price is €197
includes taxes & fees
31 May - 1 Jun
Tarrytown House Estate
Free WiFi, bed sheets

Budget Motor Inn - Stony Point

Budget Motor Inn - Stony Point
1.5 star property
12.3 km from Pleasant Square
5.2 out of 10, (557 reviews)
"Excellent "
United States
Tariq
The price is €59
includes taxes & fees
31 May - 1 Jun
Budget Motor Inn - Stony Point
Restaurant

Armoni Inn & Suites

Armoni Inn & Suites
3.5 star property
14.6 km from Pleasant Square
6.0 out of 10, (2,216 reviews)
"Good value, clean room, plenty of parking"
United States
Mohamed
The price is €68
includes taxes & fees
31 May - 1 Jun
Armoni Inn & Suites
Premium bedding, desk, blackout curtains, free WiFi

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, (1,000 reviews)
"The staffs are very friendly and rooms are clean."
United States
Anna Lorraine
The price is €108
includes taxes & fees
1 Jun - 2 Jun
Quality Inn Spring Valley - Nanuet
Standard Room, 1 King Bed

Ardsley Acres Hotel Westchester

Ardsley Acres Hotel Westchester
2.0 star property
17.1 km from Pleasant Square
8.8 out of 10, Excellent, (1,036 reviews)
"Enjoyed our stay at the motel."
United States
Elsa
The price is €127
includes taxes & fees
9 Jun - 10 Jun
Ardsley Acres Hotel Westchester
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

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
8.4
Very good
157 reviews
View
Basic Triple Room | Interior
Tappan Zee Hotel
2.0 star property
6.4
665 reviews
View
Exterior
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
2.5 star property
9.0
Wonderful
1,001 reviews
View
Free daily on-the-go breakfast
FairBridge Inn Express Nyack
2.0 star property
7.8
Good
1,001 reviews
View
Interior entrance
West Gate Inn Nyack
3.0 star property
7.2
Good
1,306 reviews
View

Top Pleasant Square Hotel Reviews

Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

2/10 Terrible
"Dirty small rooms and not well maintained. Staff is not at all helpful, they even charge $6 per bag for storage!!"
Gourav 1-night trip
Posted less than an hour ago
Sheraton New York Times Square Hotel

Hotels near other Pleasant Square attractions

Merchants Square

4.5/5 (2 reviews)
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

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 39 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 (35.5 km) from Pleasant Square. Other good options around the area include Night Hotel Broadway and Ly New York Hotel.
How many hotels should I expect to find near Pleasant Square?
Expedia has 39 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 Ossining Historical Society and Sing Sing Prison Museum. 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, Teatown Lake Reservation or Rockland Lake State Park.