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 RM1,752
RM3,900 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
7 Dec - 8 Dec
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
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, (1000)
"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 RM593
RM678 total
includes taxes & fees
18 Dec - 19 Dec
Courtyard by Marriott Tarrytown Westchester County
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
Exterior
The Abbey Inn & Spa

The Abbey Inn & Spa

4.0 star property
15.6 km from Pleasant Square
9.2 out of 10, Wonderful, (224)
"The staff, the room, the restaurant and bar were all excellent. The Abby is a special place. Beautiful architecture, great art! Location can’t be beat. "
United States
Lya
The price is RM1,166
RM1,522 total
includes taxes & fees
11 Dec - 12 Dec
The Abbey Inn & Spa
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 RM382
RM549 total
includes taxes & fees
17 Dec - 18 Dec
Hotel Nyack, a JdV by Hyatt Hotel
Exterior
The Opus Westchester, Autograph Collection

The Opus Westchester, Autograph Collection

5.0 star property
16.5 km from Pleasant Square
9.2 out of 10, Wonderful, (526)
"our room was very clean on beds very comfortable staff friendly, breakfast wonderful"
United States
Susan
The price is RM1,233
RM1,552 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Opus Westchester, Autograph Collection
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, (1018)
"Very clean very beautiful very good hospitality would stay again"
United States
Bobby
The price is RM436
RM508 total
includes taxes & fees
14 Dec - 15 Dec
DoubleTree by Hilton Hotel Nanuet
Lobby
Element Spring Valley

Element Spring Valley

3.0 star property
14.8 km from Pleasant Square
8.8 out of 10, Excellent, (429)
"Staff, cleanliness, nice breakfast"
United States
Jesus
The price is RM505
RM588 total
includes taxes & fees
14 Dec - 15 Dec
Element Spring Valley
View from property
Residence Inn Orangeburg

Residence Inn Orangeburg

3.0 star property
15.4 km from Pleasant Square
8.8 out of 10, Excellent, (1013)
"Great staff, great location "
United States
Luis
The price is RM593
RM660 total
includes taxes & fees
15 Dec - 16 Dec
Residence Inn Orangeburg
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, (1008)
"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
7 Dec - 8 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, (1012)
"Beautiful hotel, great breakfast!"
United States
Elaine
The price is RM492
RM562 total
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG
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
Indoor pool, pool loungers
Sonesta White Plains Downtown

Sonesta White Plains Downtown

4.0 star property
16.9 km from Pleasant Square
8.8 out of 10, Excellent, (1152)
"Great stay"
United States
Dedra
The price is RM647
RM876 total
includes taxes & fees
18 Dec - 19 Dec
Sonesta White Plains Downtown
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 RM533
RM610 total
includes taxes & fees
9 Dec - 10 Dec
Baymont by Wyndham White Plains - Elmsford
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, (1000)
"Excellent hotel. "
United States
Samuel
The price is RM605
RM693 total
includes taxes & fees
1 Jan - 2 Jan 2026
Hotel MTK Mount Kisco
Exterior
Residence Inn by Marriott White Plains Westchester County

Residence Inn by Marriott White Plains Westchester County

3.0 star property
16.1 km from Pleasant Square
8.6 out of 10, Excellent, (649)
"Staff very helpful "
United States
Bianca
The price is RM698
RM798 total
includes taxes & fees
2 Jan - 3 Jan 2026
Residence Inn by Marriott White Plains Westchester County
Premium bedding, desk, iron/ironing board, free WiFi
Ardsley Acres Hotel Westchester

Ardsley Acres Hotel Westchester

2.0 star property
17.1 km from Pleasant Square
8.6 out of 10, Excellent, (1000)
"Omg the rooms of this hotel are amazing and cute"
United States
Abdele
Ardsley Acres Hotel Westchester
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 RM561
RM642 total
includes taxes & fees
9 Dec - 10 Dec
Hampton Inn White Plains/Tarrytown
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

Empire Hotel

Empire Hotel

10/10 Excellent
"Friendly check-in staff"
Angela 1-night trip
Posted 15 hours ago
Empire 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.