Default HTG hotel image

Find hotels near Pleasant Square, Ossining from AED 448

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
6 Nov - 8 Nov
Next weekend
13 Nov - 15 Nov

Filter by

Property class

Guest rating

Selecting then applying a filter from this group will update the results on a new page

Our top choices for Pleasant Square hotels

An aerial view of a campus with multiple buildings, a river, and surrounding greenery.

1. Windrose On Hudson

Windrose On Hudson
3.0 star property
3.1 km from Pleasant Square
8.6 out of 10, Excellent, (283 reviews)
"Would 100% stay again"
United States
Michael
The price is AED 555
AED 618 total
includes taxes & fees
22 Nov - 23 Nov
Windrose On Hudson
A spacious living room with a large window, a ceiling fan, a dining area with a table and chairs, and a staircase leading to an upper level.

2. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
0.7 km from Pleasant Square
The price is AED 1,802
AED 3,748 total
includes taxes & fees
9 Nov - 10 Nov
Summer Pool Oasis Custom Bar Arcade Pool Table
Indoor pool

3. 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, (1,188 reviews)
"Great place"
United States
Joel
The price is AED 465
AED 541 total
includes taxes & fees
22 Nov - 23 Nov
DoubleTree by Hilton Hotel Nanuet
A modern hotel lobby with a kitchen area, seating arrangements, and large windows offering a view of the outdoors.

4. 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, (1,897 reviews)
"Went for Halloween weekend it was very nice pool was nice as well there a Dunkin’ 3 min walking distance and a 7 min drive to tarry town it was wonderful"
United States
Omari
The price is AED 487
AED 557 total
includes taxes & fees
29 Nov - 30 Nov
Baymont by Wyndham White Plains - Elmsford
A modern lounge with leather sofas, a patterned rug, and red pendant lights.

5. 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, (1,326 reviews)
"Great stay!"
United States
Kristen
The price is AED 417
AED 576 total
includes taxes & fees
2 Dec - 3 Dec
Hotel Nyack, a JdV by Hyatt Hotel
A hotel with a modern facade, a prominent signage for SpringHill Suites Marriott, and a covered entrance area with seating.

6. SpringHill Suites by Marriott Tarrytown Westchester County

SpringHill Suites by Marriott Tarrytown Westchester County
3.0 star property
11.2 km from Pleasant Square
8.8 out of 10, Excellent, (1,006 reviews)
"Clean, friendly staff, would stay again"
United States
Gwen
The price is AED 572
AED 654 total
includes taxes & fees
15 Nov - 16 Nov
SpringHill Suites by Marriott Tarrytown Westchester County
A hotel room with a wooden headboard, a bedside table with a lamp, and a bed with white bedding and pillows.

7. Ardsley Acres Hotel Westchester

Ardsley Acres Hotel Westchester
2.0 star property
17.1 km from Pleasant Square
8.8 out of 10, Excellent, (1,266 reviews)
"Great Stay"
United States
Wendell
The price is AED 459
AED 525 total
includes taxes & fees
5 Nov - 6 Nov
Ardsley Acres Hotel Westchester
A modern reception area with a wooden reception desk, a blue accent wall, and a large glass door leading to an outdoor seating area.

8. 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, (1,000 reviews)
"Great stay"
United States
Sean P.
The price is AED 544
AED 622 total
includes taxes & fees
2 Dec - 3 Dec
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
A modern kitchen with a central island, bar stools, a fireplace, and a contemporary pendant light.

9. 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)
"Very clean property with pleasant staff."
United States
Syble
The price is AED 558
AED 639 total
includes taxes & fees
19 Nov - 20 Nov
Courtyard by Marriott Tarrytown Westchester County
A spacious lobby with a red sofa, green armchairs, a fireplace, and a staircase leading to an upper level.

10. Hotel MTK Mount Kisco

Hotel MTK Mount Kisco
3.0 star property
13.2 km from Pleasant Square
8.6 out of 10, Excellent, (1,002 reviews)
"This hotel served our purposes very well."
United States
Joseph
The price is AED 539
AED 617 total
includes taxes & fees
15 Nov - 16 Nov
Hotel MTK Mount Kisco
A spacious lobby with a reception desk, sofas, and a coffee table. There are multiple seating areas and a large window providing natural light.

11. Sheraton Tarrytown Hotel

Sheraton Tarrytown Hotel
3.5 star property
11.4 km from Pleasant Square
8.4 out of 10, Very good, (1,000 reviews)
"Nice stay"
United States
Kerry-Anna
The price is AED 497
AED 568 total
includes taxes & fees
22 Nov - 23 Nov
Sheraton Tarrytown Hotel
A spacious hotel lobby with a modern design, featuring a large seating area, a dining table, and large windows providing views of the outdoors.

12. Element by Marriott Spring Valley

Element by Marriott Spring Valley
3.0 star property
14.8 km from Pleasant Square
8.8 out of 10, Excellent, (558 reviews)
"Delicious breakfast, clean room, nice gym!"
United States
Rohan
The price is AED 492
AED 573 total
includes taxes & fees
22 Nov - 23 Nov
Element by Marriott Spring Valley
A modern lobby with seating areas, a fireplace, and a flat-screen TV mounted on the wall.

13. Cambria Hotel & Suites - White Plains Downtown

Cambria Hotel & Suites - White Plains Downtown
3.5 star property
16.5 km from Pleasant Square
9.2 out of 10, Wonderful, (1,004 reviews)
"Very conveniently located hotel, and great service"
United States
Anthony
The price is AED 702
AED 803 total
includes taxes & fees
29 Nov - 30 Nov
Cambria Hotel & Suites - White Plains Downtown
A hotel lobby with seating areas, tables, a reception desk, and a TV mounted on the wall.

14. Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown
3.0 star property
12 km from Pleasant Square
7.8 out of 10, Good, (1,722 reviews)
"The room was pretty clean and comfortable, staff was friendly"
United States
Zack
The price is AED 416
AED 475 total
includes taxes & fees
22 Nov - 23 Nov
Hampton Inn White Plains/Tarrytown
A hotel patio with outdoor seating, a fire pit, and a covered area with glass doors.

15. Residence Inn Orangeburg

Residence Inn Orangeburg
3.0 star property
15.4 km from Pleasant Square
8.8 out of 10, Excellent, (1,003 reviews)
"Great property!! Great staff!! Clean and lots of room!!"
United States
KAREN
The price is AED 526
AED 585 total
includes taxes & fees
29 Nov - 30 Nov
Residence Inn Orangeburg
A breakfast area with multiple tables and chairs, a kitchen area with appliances, and a sign for Daybreak Breakfast.

16. Days Inn by Wyndham Elmsford / White Plains

Days Inn by Wyndham Elmsford / White Plains
2.0 star property
12.4 km from Pleasant Square
7.4 out of 10, Good, (1,027 reviews)
"Great place to stay, extremely friendly and helpful staff"
United States
Frankie
The price is AED 392
AED 448 total
includes taxes & fees
22 Nov - 23 Nov
Days Inn by Wyndham Elmsford / White Plains
A large, historic building with a prominent tower, surrounded by well-maintained gardens and a parking area.

17. The Abbey Inn & Spa

The Abbey Inn & Spa
4.0 star property
15.6 km from Pleasant Square
9.4 out of 10, Exceptional, (281 reviews)
"Room was clean, staff was pleasant... overall great stay"
United States
Lina
The price is AED 1,246
AED 1,594 total
includes taxes & fees
9 Nov - 10 Nov
The Abbey Inn & Spa
A Holiday Inn Express & Suites sign with a bench and flower beds in front.

18. Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG
2.5 star property
14.4 km from Pleasant Square
9.2 out of 10, Wonderful, (1,002 reviews)
"Very clean, great staff, great breakfast."
United States
John
The price is AED 511
AED 584 total
includes taxes & fees
15 Nov - 16 Nov
Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG
A checkered floor, a potted plant, and two metal ladders in a room with large windows.

19. West Gate Inn Nyack

West Gate Inn Nyack
3.0 star property
9.6 km from Pleasant Square
7.4 out of 10, Good, (1,509 reviews)
"Awesome place will still again if in area"
United States
Joshua
The price is AED 405
AED 464 total
includes taxes & fees
5 Nov - 6 Nov
West Gate Inn Nyack
An indoor swimming pool with clear water, surrounded by lounge chairs and a seating area.

20. Sonesta White Plains Downtown

Sonesta White Plains Downtown
4.0 star property
17 km from Pleasant Square
9.0 out of 10, Wonderful, (1,353 reviews)
"Well, maintained property and great location!"
United States
Laura
The price is AED 613
AED 823 total
includes taxes & fees
22 Nov - 23 Nov
Sonesta White Plains Downtown
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

Hotels recommended for families near Pleasant Square

A modern living room with a large window, a sofa with patterned cushions, a wooden coffee table, and a painting on the wall.

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Ossining
8.8 out of 10, Excellent, (10)
The price is AED 1,380
AED 2,936 total
includes taxes & fees
9 Nov - 10 Nov
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Top Pleasant Square Hotel Reviews

Hotel Edison Times Square

Hotel Edison Times Square

10/10 Excellent
"Great location for theatres."
Brian 3-night trip
Posted 1 hour ago
Hotel Edison Times Square

Other attractions near Pleasant Square

Merchants Square

9.0/10 (2 reviews)
Explore the great outdoors at Merchants Square, a lovely green space in Ossining. Stroll along the riverfront or attend a sporting event in this quaint area.
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 traveler data, and this hotel offers a restaurant and a 24-hour fitness center. You'll find it 22 mi (35.5 km) from Pleasant Square. Other good options around the area include Night Hotel Broadway and Hotel Belleclaire Central Park, a Small Luxury Hotel.
How many hotels can I expect to find near Pleasant Square?
Expedia has 36 hotels and other accommodations 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, you'll find most room reservations are fully refundable if you cancel prior to the hotel's cancellation deadline, which is usually within 24-48 hours of your arrival date. If your reservation is non-refundable, you might be able to cancel it and receive a refund within a 24-hour period of booking. Add your dates and click on "Search", then you can filter by "fully refundable" to review top deals close to Pleasant Square.
Where can I learn more about changing or cancelling my trip in the area near Pleasant Square?
For additional details about updating your stay near Pleasant Square or cancelling it, go to https://www.expedia.com/service/.
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. Van Cortlandt Manor, Sleepy Hollow Cemetery, and Old Dutch Church of Sleepy Hollow are some of the local landmarks to explore. Consider spending a leisurely afternoon outside at Croton Point Park, Rockland Lake State Park, or Louis Engel Waterfront Park.