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25 Nov - 26 Nov
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Top Trending 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, (89)
"Clean rooms, quiet, beautiful grounds"
United States
patricia
The price is ฿4,962
฿5,526 total
includes taxes & fees
1 Dec - 2 Dec
Windrose On Hudson
House | 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 ฿15,272
฿32,356 total
includes taxes & fees
1 Dec - 2 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, (941)
"Great hotel to enjoy all the SleepHollow excursions. "
United States
Michelle
The price is ฿4,635
฿5,301 total
includes taxes & fees
30 Nov - 1 Dec
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
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, (1010)
"Great staff , clean rooms, good breakfast "
United States
Stephen
The price is ฿2,280
฿2,721 total
includes taxes & fees
4 Dec - 5 Dec
Days Inn by Wyndham Elmsford / White Plains
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, (1012)
"Awesome place"
United States
Nichole
The price is ฿2,999
฿4,307 total
includes taxes & fees
1 Dec - 2 Dec
Hotel Nyack, a JdV by Hyatt Hotel
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, (1012)
"Was a good stay."
United States
Kelly
The price is ฿3,603
฿4,120 total
includes taxes & fees
26 Nov - 27 Nov
Sleepy Hollow Hotel
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, (1465)
"Great experience can’t wait to come back "
United States
Marvin
The price is ฿4,320
฿4,940 total
includes taxes & fees
1 Dec - 2 Dec
Baymont by Wyndham White Plains - Elmsford
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, (1005)
"Always a pleasant place "
United States
Abner
The price is ฿2,881
฿3,295 total
includes taxes & fees
30 Nov - 1 Dec
Inn on the Hudson
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, (1012)
"The heat and air conditioning were good. Hotel staff were friendly. "
United States
Ira
The price is ฿3,379
฿3,865 total
includes taxes & fees
30 Nov - 1 Dec
Extended Stay America Suites White Plains Elmsford
Reception
Westchester Marriott

Westchester Marriott

4.5 star property
11.7 km from Pleasant Square
8.8 out of 10, Excellent, (430)
"Had a great stay!"
United States
Brionna
The price is ฿4,962
฿5,675 total
includes taxes & fees
14 Dec - 15 Dec
Westchester Marriott
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, (1163)
"Clean rooms nice breakfast and amenities "
United States
Diane
The price is ฿3,884
฿4,442 total
includes taxes & fees
28 Nov - 29 Nov
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, (916)
"Very affordable compared to surrounding hotels"
United States
CRAIG A
The price is ฿3,204
฿3,665 total
includes taxes & fees
26 Nov - 27 Nov
Motel 6 Elmsford, NY - White Plains
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, (1005)
"The hotel did the job. Staff was great and accommodating. It was clean and rooms were nice. "
United States
Alex
The price is ฿4,925
฿5,633 total
includes taxes & fees
30 Nov - 1 Dec
SpringHill Suites by Marriott Tarrytown Westchester County
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, (1008)
"Beautiful hotel, great breakfast!"
United States
Elaine
The price is ฿3,858
฿4,413 total
includes taxes & fees
30 Nov - 1 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, (1287)
"Will definitely stay again"
United States
Elainne
The price is ฿4,402
฿5,035 total
includes taxes & fees
2 Dec - 3 Dec
Hampton Inn White Plains/Tarrytown
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, (1002)
"Great stay"
United States
Deon Francine
The price is ฿3,274
฿3,810 total
includes taxes & fees
26 Nov - 27 Nov
Days Inn by Wyndham Nanuet / Spring Valley
Reception
FairBridge Inn Express Nyack

FairBridge Inn Express Nyack

2.0 star property
9.8 km from Pleasant Square
7.6 out of 10, Good, (1007)
"Clean room, friendly staff, good location "
Canada
Andrew
The price is ฿3,026
฿3,613 total
includes taxes & fees
2 Dec - 3 Dec
FairBridge Inn Express Nyack
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, (1008)
"Very clean very beautiful very good hospitality would stay again"
United States
Bobby
The price is ฿3,424
฿3,985 total
includes taxes & fees
7 Dec - 8 Dec
DoubleTree by Hilton Hotel Nanuet
Basic Triple Room | Interior
Tappan Zee Hotel

Tappan Zee Hotel

2.0 star property
10.4 km from Pleasant Square
6.2 out of 10, (643)
"We had a good stay, but the shower was messed up. Other than that, it was fine."
United States
Kizuwanda
Tappan Zee Hotel
Restaurant
Armoni Inn & Suites

Armoni Inn & Suites

3.5 star property
14.6 km from Pleasant Square
6.0 out of 10, (2170)
"It was a quiet place with comfortable beds "
United States
Rob
Armoni Inn & Suites
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

Top Pleasant Square Hotel Reviews

Hyatt Grand Central New York

Hyatt Grand Central New York

10/10 Excellent
"Great location"
donald 4-night trip
Posted 10 hours ago
Hyatt Grand Central New York

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 Empire 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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