Hotels near Pleasant Square

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Top 10 Hotels Near Pleasant Square

Terrace/patio
Windrose On Hudson

Windrose On Hudson

3.0 star property
3.1 km from Pleasant Square
8.0 out of 10, Very good, (94)
"Clean rooms, quiet, beautiful grounds"
United States
patricia
The price is RM603
RM672 total
includes taxes & fees
14 Dec - 15 Dec
Windrose On Hudson
5 bedrooms
Foliage at Westchester Manor - Near Sleepy Hollow

Foliage at Westchester Manor - Near Sleepy Hollow

2.0 star property
0.7 km from Pleasant Square
The price is RM1,755
RM3,908 total
includes taxes & fees
8 Dec - 9 Dec
Foliage at Westchester Manor - Near Sleepy Hollow
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
8.8 out of 10, Excellent, (944)
"Great hotel to enjoy all the SleepHollow excursions. "
United States
Michelle
The price is RM591
RM676 total
includes taxes & fees
17 Dec - 18 Dec
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
Lobby
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, (1000)
"Room was clean, staff was pleasant, hotel overall was great"
United States
Cara
The price is RM383
RM550 total
includes taxes & fees
15 Dec - 16 Dec
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, (1009)
"Our stay was very cozy and comfortable. Our room was clean and had a great view. Conveniently located for our plans. Would recommend "
United States
Donald
The price is RM559
RM639 total
includes taxes & fees
21 Dec - 22 Dec
Courtyard by Marriott Tarrytown Westchester County
Breakfast and dinner served, American cuisine
Sleepy Hollow Hotel

Sleepy Hollow Hotel

3.5 star property
11.3 km from Pleasant Square
6.8 out of 10, (1030)
"excellent place "
United States
Boruch
The price is RM505
RM578 total
includes taxes & fees
7 Dec - 8 Dec
Sleepy Hollow Hotel
Reception
Westchester Marriott

Westchester Marriott

4.5 star property
11.7 km from Pleasant Square
8.8 out of 10, Excellent, (436)
"Staff was friendly hotel is beautiful"
United States
Doris
The price is RM634
RM725 total
includes taxes & fees
14 Dec - 15 Dec
Westchester Marriott
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, (1479)
"Great experience can’t wait to come back "
United States
Marvin
The price is RM541
RM619 total
includes taxes & fees
11 Dec - 12 Dec
Baymont by Wyndham White Plains - Elmsford
Exterior
Extended Stay America Suites White Plains Elmsford

Extended Stay America Suites White Plains Elmsford

2.5 star property
12 km from Pleasant Square
6.8 out of 10, (1014)
"The heat and air conditioning were good. Hotel staff were friendly. "
United States
Ira
The price is RM424
RM485 total
includes taxes & fees
15 Dec - 16 Dec
Extended Stay America Suites White Plains Elmsford
Lobby
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, (1001)
"Clean room 👍 Staff is friendly and welcoming 😊 Breakfast was good 👍 Thank you !! Will be booking again in the near future "
United States
sharon
The price is RM415
RM489 total
includes taxes & fees
29 Dec - 30 Dec
Days Inn by Wyndham Elmsford / White Plains
View from property
Inn on the Hudson

Inn on the Hudson

2.0 star property
15.3 km from Pleasant Square
6.8 out of 10, (1001)
"Always a pleasant place "
United States
Abner
The price is RM368
RM421 total
includes taxes & fees
7 Dec - 8 Dec
Inn on the Hudson
Exterior
SpringHill Suites by Marriott Tarrytown Westchester County

SpringHill Suites by Marriott Tarrytown Westchester County

3.0 star property
11.1 km from Pleasant Square
8.4 out of 10, Very good, (1007)
"The hotel did the job. Staff was great and accommodating. It was clean and rooms were nice. "
United States
Alex
The price is RM628
RM718 total
includes taxes & fees
1 Jan - 2 Jan 2026
SpringHill Suites by Marriott Tarrytown Westchester County
Lobby
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, (1017)
"Very clean very beautiful very good hospitality would stay again"
United States
Bobby
The price is RM437
RM509 total
includes taxes & fees
14 Dec - 15 Dec
DoubleTree by Hilton Hotel Nanuet
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, (1176)
"Always a great stay when I visit the area. "
United States
Joseph
The price is RM495
RM566 total
includes taxes & fees
26 Dec - 27 Dec
West Gate Inn Nyack
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, (918)
"Very affordable compared to surrounding hotels"
United States
CRAIG A
The price is RM409
RM468 total
includes taxes & fees
4 Dec - 5 Dec
Motel 6 Elmsford, NY - White Plains
Exterior
Sheraton Tarrytown Hotel

Sheraton Tarrytown Hotel

3.5 star property
11.4 km from Pleasant Square
8.4 out of 10, Very good, (1001)
"Very awsome hotel!!! It had charm!"
United States
kimberli
The price is RM559
RM639 total
includes taxes & fees
14 Dec - 15 Dec
Sheraton Tarrytown 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

2.5 star property
14.4 km from Pleasant Square
9.2 out of 10, Wonderful, (1012)
"Beautiful hotel, great breakfast!"
United States
Elaine
The price is RM492
RM562 total
includes taxes & fees
17 Dec - 18 Dec
Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG
Meeting facility
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, (1282)
"Will definitely stay again"
United States
Elainne
The price is RM562
RM643 total
includes taxes & fees
8 Dec - 9 Dec
Hampton Inn White Plains/Tarrytown
Interior
Tappan Zee Hotel

Tappan Zee Hotel

2.0 star property
10.4 km from Pleasant Square
6.4 out of 10, (644)
"We had a good stay, but the shower was messed up. Other than that, it was fine."
United States
Kizuwanda
Tappan Zee Hotel
Exterior
Days Inn by Wyndham Nanuet / Spring Valley

Days Inn by Wyndham Nanuet / Spring Valley

2.0 star property
15.4 km from Pleasant Square
6.8 out of 10, (1001)
"Great stay"
United States
Deon Francine
The price is RM440
RM511 total
includes taxes & fees
15 Dec - 16 Dec
Days Inn by Wyndham Nanuet / 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.
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Top Pleasant Square Hotel Reviews

Paramount Times Square – A Generator Hotel

Paramount Times Square – A Generator Hotel

10/10 Excellent
"I enjoyed my stay!"
Jazmine 3-night trip
Posted 3 days ago
Paramount Times Square – A Generator 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 Sheraton New York Times Square Hotel.
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 Croton Landing Park.

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