Ossining Pleasant Square Hotels

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Check prices for these dates

Tonight
14 Jan - 15 Jan
Tomorrow
15 Jan - 16 Jan
This weekend
16 Jan - 18 Jan
Next weekend
23 Jan - 25 Jan

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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
8.2 out of 10, Very good, (107 reviews)
"Clean room, staff were very welcoming"
United States
Semaj
The price is HK$1,383
HK$1,541 total
includes taxes & fees
12 Feb - 13 Feb
Windrose On Hudson
5 bedrooms

NEW 45 Wolden Rd Ossining NY 10562

NEW 45 Wolden Rd Ossining NY 10562
2.0 star property
0.7 km from Pleasant Square
The price is HK$2,566
HK$6,719 total
includes taxes & fees
21 Jan - 22 Jan
NEW 45 Wolden Rd Ossining NY 10562
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, (976 reviews)
"great stay"
United States
Janet
The price is HK$1,045
HK$1,195 total
includes taxes & fees
25 Jan - 26 Jan
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
8.2 out of 10, Very good, (1,495 reviews)
"Enjoyed the free breakfast and the workout room had options; great location for access into city"
United States
Kathleen Elizabeth
The price is HK$902
HK$1,031 total
includes taxes & fees
1 Feb - 2 Feb
Baymont by Wyndham White Plains - Elmsford
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, (1,000 reviews)
"Clean room , staff and amenities were all great"
United States
Elzie
The price is HK$828
HK$1,159 total
includes taxes & fees
29 Jan - 30 Jan
Hotel Nyack, a JdV by Hyatt 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 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 HK$1,054
HK$1,205 total
includes taxes & fees
25 Jan - 26 Jan
Courtyard by Marriott Tarrytown Westchester County
Aerial view

Sleepy Hollow Hotel

Sleepy Hollow Hotel
3.5 star property
11.3 km from Pleasant Square
6.8 out of 10, (1,000 reviews)
"Overall the staff was great and the rooms were nice!"
United States
Ashley
The price is HK$1,009
HK$1,154 total
includes taxes & fees
12 Feb - 13 Feb
Sleepy Hollow Hotel
Terrace/patio

Westchester Marriott

Westchester Marriott
4.5 star property
11.7 km from Pleasant Square
8.8 out of 10, Excellent, (466 reviews)
"Comfy bed and nice breakfast!"
United States
Ignacio
The price is HK$1,180
HK$1,350 total
includes taxes & fees
15 Feb - 16 Feb
Westchester Marriott
Restaurant

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, (1,001 reviews)
"Good for a short stay! "
United States
NUTAN
The price is HK$731
HK$863 total
includes taxes & fees
31 Jan - 1 Feb
Days Inn by Wyndham Elmsford / White Plains
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, (1,010 reviews)
"Room was clean and great size."
Canada
Robert
The price is HK$1,120
HK$1,281 total
includes taxes & fees
25 Jan - 26 Jan
SpringHill Suites by Marriott Tarrytown Westchester County
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, (1,212 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, 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, (1,031 reviews)
"Nice clean hotel with friendly staff. "
United States
michelle
The price is HK$723
HK$841 total
includes taxes & fees
1 Feb - 2 Feb
DoubleTree by Hilton Hotel Nanuet
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, (1,001 reviews)
"great comfortable stay !"
United States
Niesha
The price is HK$1,054
HK$1,205 total
includes taxes & fees
25 Jan - 26 Jan
Sheraton Tarrytown Hotel
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, (1,340 reviews)
"Room was clean, staff was friendly and the hotel was conveniently located to my destination."
United States
melissa
The price is HK$953
HK$1,090 total
includes taxes & fees
23 Jan - 24 Jan
Hampton Inn White Plains/Tarrytown
Lobby

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 HK$772
HK$883 total
includes taxes & fees
18 Jan - 19 Jan
Motel 6 Elmsford, NY - White Plains
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$897
HK$1,026 total
includes taxes & fees
25 Jan - 26 Jan
Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley 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
7.6 out of 10, Good, (1,002 reviews)
"The staff was really friendly and the place is clean"
Canada
Sara
The price is HK$675
HK$806 total
includes taxes & fees
25 Jan - 26 Jan
FairBridge Inn Express Nyack
Interior

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
3.5 star property
12.5 km from Pleasant Square
8.2 out of 10, Very good, (1,008 reviews)
"Hotel was beautiful and clean "
United States
April
The price is HK$938
HK$1,268 total
includes taxes & fees
20 Jan - 21 Jan
Tarrytown House Estate
Interior entrance

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, (1,001 reviews)
"Great hotel. The town is nice. "
United States
Eric
The price is HK$1,081
HK$1,236 total
includes taxes & fees
1 Feb - 2 Feb
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

Hotel Edison Times Square

Hotel Edison Times Square

10/10 Excellent
"Excellent "
Agnes Milagros 1-night trip
Posted 14 hours ago
Hotel Edison 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 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 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 traveller data, and this hotel offers a restaurant and a 24-hour fitness centre. 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 should I expect to find near Pleasant Square?
Expedia has 38 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 Teatown Lake Reservation.