Search Hotels Near Pleasant Square, Ossining

  • 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
10 May - 11 May
Tomorrow
11 May - 12 May
Next weekend
15 May - 17 May
In two weeks
22 May - 24 May

Filter by

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
8.4 out of 10, Very good, (134 reviews)
"Very pleasant stay. "
United States
Beth
The price is 4.337.828 ₫
4.831.648 ₫ total
includes taxes & fees
24 May - 25 May
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, (1,005 reviews)
"Clean rooms, good breakfast "
United States
Santa
The price is 3.814.805 ₫
4.363.085 ₫ total
includes taxes & fees
28 May - 29 May
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
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, (1,686 reviews)
"Room was very clean and spacious. Hotel overall was very well kept. Breakfast was very good."
United States
Erinn
The price is 3.346.505 ₫
3.827.565 ₫ total
includes taxes & fees
14 May - 15 May
Baymont by Wyndham White Plains - Elmsford
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, (1,003 reviews)
"Great hidden gem"
United States
Jaime
The price is 4.235.749 ₫
4.844.638 ₫ total
includes taxes & fees
24 May - 25 May
Courtyard by Marriott Tarrytown Westchester County
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, (1,087 reviews)
"Great stay "
United States
James
The price is 2.788.754 ₫
3.902.349 ₫ total
includes taxes & fees
31 May - 1 Jun
Hotel Nyack, a JdV by Hyatt Hotel
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, (1,010 reviews)
"Enjoyed our stay"
United States
Piper
The price is 4.002.914 ₫
4.578.332 ₫ total
includes taxes & fees
17 May - 18 May
SpringHill Suites by Marriott Tarrytown Westchester County
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, (1,439 reviews)
"Staff was absolutely wonderful."
United States
Lisa
The price is 3.086.046 ₫
3.529.616 ₫ total
includes taxes & fees
7 Jun - 8 Jun
Hampton Inn White Plains/Tarrytown
Terrace/patio

Westchester Marriott

Westchester Marriott
4.5 star property
11.7 km from Pleasant Square
8.8 out of 10, Excellent, (545 reviews)
"Staff member Diana at the bar/resturaunt was so helpful and kind. I appreciated her hospitality "
United Kingdom
Mariana
The price is 4.897.420 ₫
5.601.424 ₫ total
includes taxes & fees
24 May - 25 May
Westchester Marriott
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, (1,279 reviews)
"Clean room, parking available."
United States
ashraf
The price is 2.604.328 ₫
2.978.705 ₫ total
includes taxes & fees
11 May - 12 May
West Gate Inn Nyack
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, (1,124 reviews)
"Very nice stay. Clean room. Restaurant was good for breakfast. Liked the hot tub."
United States
David
The price is 3.438.323 ₫
4.001.347 ₫ total
includes taxes & fees
18 May - 19 May
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
7.8 out of 10, Good, (1,002 reviews)
"Good value"
United States
Chip
The price is 2.459.892 ₫
2.936.494 ₫ total
includes taxes & fees
17 May - 18 May
FairBridge Inn Express Nyack
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)
"Excellent service and great location for value "
United States
Alice
The price is 4.002.914 ₫
4.578.331 ₫ total
includes taxes & fees
21 May - 22 May
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)
"Nice stay. Friendly staff"
United States
Jared
The price is 3.753.768 ₫
4.293.372 ₫ total
includes taxes & fees
25 May - 26 May
Hotel MTK Mount Kisco
Exterior

Tarrytown House Estate

Tarrytown House Estate
3.5 star property
12.5 km from Pleasant Square
8.2 out of 10, Very good, (1,069 reviews)
"Great hotel, perfect location. Loved everything about it, front desk staff was wonderful."
United States
Margaret
The price is 3.555.661 ₫
4.724.570 ₫ total
includes taxes & fees
17 May - 18 May
Tarrytown House Estate
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, (660 reviews)
"Parking spacious Mall convenient Price affordable "
United States
dalia
The price is 2.237.844 ₫
2.604.065 ₫ total
includes taxes & fees
11 May - 12 May
Tappan Zee Hotel
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, (1,003 reviews)
"Great place to stay. "
United States
Jennifer
The price is 4.156.822 ₫
4.754.363 ₫ total
includes taxes & fees
13 May - 14 May
Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG
Restaurant

Armoni Inn & Suites

Armoni Inn & Suites
3.5 star property
14.6 km from Pleasant Square
6.0 out of 10, (2,203 reviews)
"Dirtiest place I have ever stayed at."
United States
Ilan
The price is 1.870.570 ₫
2.083.147 ₫ total
includes taxes & fees
11 May - 12 May
Armoni Inn & Suites
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, (959 reviews)
"Parking good. HVAC good. Bath good. Room floor a little disheveled. Needed more lamps. Very convenient."
United States
Bruce
The price is 2.999.226 ₫
3.430.431 ₫ total
includes taxes & fees
11 May - 12 May
Motel 6 Elmsford, NY - White Plains
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, (1,002 reviews)
"The staffs are very friendly and rooms are clean."
United States
Anna Lorraine
The price is 2.344.132 ₫
2.727.984 ₫ total
includes taxes & fees
31 May - 1 Jun
Quality Inn Spring Valley - Nanuet
Lobby

Element Spring Valley

Element Spring Valley
3.0 star property
14.8 km from Pleasant Square
8.8 out of 10, Excellent, (480 reviews)
"Great place to stay."
United States
Jean Fritz Junior
The price is 3.762.187 ₫
4.378.244 ₫ total
includes taxes & fees
25 May - 26 May
Element Spring Valley
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
134 reviews
View
Exterior
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
2.5 star property
9.0
Wonderful
1,005 reviews
View
Free daily self-service breakfast
Baymont by Wyndham White Plains - Elmsford
2.5 star property
8.4
Very good
1,686 reviews
View
Property amenity
Courtyard by Marriott Tarrytown Westchester County
3.0 star property
9.0
Wonderful
1,003 reviews
View
Restaurant
Hotel Nyack, a JdV by Hyatt Hotel
4.0 star property
8.6
Excellent
1,087 reviews
View

Top Pleasant Square Hotel Reviews

The Manhattan at Times Square

The Manhattan at Times Square

4/10 Poor
"Went to drop off our luggage before room was ready and they demanded a tip. If I knew I would just leave it at my last stay since they don’t charge and it’s not super inconvenient for me to go back anyways. Coffee machine was broken. I was aware of construction and knew what I signed up for but really didn’t expect them to work on the room directly above and every morning it sounded like they will break through the ceiling. Even if they just skip a room or an entire floor would have made a huge difference."
Kevin 3-night trip
Posted 2 hours ago
The Manhattan at Times Square

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 quaint 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 40 hotels and other accommodations within a few miles for a convenient home base.
How many hotels should I expect to find near Pleasant Square?
Expedia has 40 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, Teatown Lake Reservation or Rockland Lake State Park.