Ossining Pleasant Square Hotels

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Check prices for these dates

Tonight
7 Jan - 8 Jan
Tomorrow
8 Jan - 9 Jan
This weekend
9 Jan - 11 Jan
Next weekend
16 Jan - 18 Jan

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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)
"Clean room, staff were very welcoming"
United States
Semaj
The price is HK$1,570
HK$1,749 total
includes taxes & fees
22 Jan - 23 Jan
Windrose On Hudson
5 bedrooms
NEW 45 Wolden Rd Ossining NY 10562

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$2,348
HK$6,260 total
includes taxes & fees
12 Jan - 13 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

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, (971)
"great stay"
United States
Janet
The price is HK$1,043
HK$1,193 total
includes taxes & fees
22 Jan - 23 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

Baymont by Wyndham White Plains - Elmsford
2.5 star property
10.9 km from Pleasant Square
8.2 out of 10, Very good, (1487)
"Enjoyed the free breakfast and the workout room had options; great location for access into city"
United States
Kathleen Elizabeth
The price is HK$894
HK$1,022 total
includes taxes & fees
19 Jan - 20 Jan
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, (1002)
"Clean room , staff and amenities were all great"
United States
Elzie
The price is HK$1,051
HK$1,413 total
includes taxes & fees
20 Jan - 21 Jan
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, (1001)
"Nice clean place.. friendly staff .. fireplace in lobby perfect for chillin "
United States
Adam
The price is HK$1,113
HK$1,273 total
includes taxes & fees
8 Feb - 9 Feb
Courtyard 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, (1013)
"I loved my stay Staff was respectful and very hospitable Pool was warm And there was a lot of parking space available "
United States
Angelica
The price is HK$947
HK$1,083 total
includes taxes & fees
1 Feb - 2 Feb
Sleepy Hollow Hotel
Terrace/patio
Westchester Marriott

Westchester Marriott

Westchester Marriott
4.5 star property
11.7 km from Pleasant Square
8.8 out of 10, Excellent, (460)
"Comfy bed and nice breakfast!"
United States
Ignacio
The price is HK$1,178
HK$1,348 total
includes taxes & fees
18 Jan - 19 Jan
Westchester Marriott
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, (1000)
"My two day stay was really nice. The room was nice and clean, staff were very nice and professional and my stay was very comfortable. Thank you."
United States
Dick
The price is HK$753
HK$889 total
includes taxes & fees
5 Feb - 6 Feb
Days Inn by Wyndham Elmsford / White Plains
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, (1005)
"Room was clean and great size."
Canada
Robert
The price is HK$1,118
HK$1,279 total
includes taxes & fees
11 Jan - 12 Jan
SpringHill Suites by Marriott Tarrytown Westchester County
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, (1208)
"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
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, (1002)
"great comfortable stay !"
United States
Niesha
The price is HK$1,052
HK$1,204 total
includes taxes & fees
1 Feb - 2 Feb
Sheraton Tarrytown Hotel
Indoor pool, open 8:30 AM to 9:30 PM, pool 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
8.8 out of 10, Excellent, (1032)
"Good food hot tub great bed was wonderful area beautiful staff so nice"
United States
vontisha
The price is HK$722
HK$840 total
includes taxes & fees
1 Feb - 2 Feb
DoubleTree by Hilton Hotel Nanuet
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, (939)
"Easy parking, lots of restaurants near, dogs are welcome, beds are old, "
United States
kathy
The price is HK$771
HK$882 total
includes taxes & fees
8 Feb - 9 Feb
Motel 6 Elmsford, NY - White Plains
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, (1337)
"Room was clean, staff was friendly and the hotel was conveniently located to my destination."
United States
melissa
The price is HK$951
HK$1,088 total
includes taxes & fees
1 Feb - 2 Feb
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, (1003)
"The staff was really friendly and the place is clean"
Canada
Sara
The price is HK$653
HK$780 total
includes taxes & fees
21 Jan - 22 Jan
FairBridge Inn Express Nyack
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)
"We had a good stay, but the shower was messed up. Other than that, it was fine."
United States
Kizuwanda
Tappan Zee Hotel
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

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, (1005)
"Very comfortable beds,clean and breakfast was great."
United States
Dawn
The price is HK$927
HK$1,060 total
includes taxes & fees
25 Jan - 26 Jan
Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG
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, (1021)
"Everything was peaceful, clean and the attached restaurant was excellent. "
United States
Henry
The price is HK$1,042
HK$1,387 total
includes taxes & fees
12 Jan - 13 Jan
Tarrytown House Estate
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, (1002)
"very nice staff the room was clean good light enough outlets comfortable bed good water pressure in shower"
United States
Marie
The price is HK$1,079
HK$1,234 total
includes taxes & fees
8 Feb - 9 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

Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

10/10 Excellent
"Very clean room and nice location. My family of 4 stay in a 2 double bed room and had sufficient space."
Cheryl 4-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 36 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 Homewood Suites by Hilton East Rutherford - Meadowlands.
How many hotels should I expect to find near Pleasant Square?
Expedia has 36 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 Rockwood Hall Park.