The Best Hotels Closest to Pleasant Square in Ossining for 2026

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Our top choices for Pleasant Square hotels

Room, 1 Queen Bed, Mobility Accessible | Desk, laptop workspace, iron/ironing board, cribs (free)

1. Windrose On Hudson

3.1 km from Pleasant Square

Mitchell

AED 776 total

includes taxes & fees

18 Aug - 19 Aug

2. Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

8.5 km from Pleasant Square

Lorraine

AED 521 total

includes taxes & fees

2 Sep - 3 Sep

3. Courtyard by Marriott Tarrytown Westchester County

10.9 km from Pleasant Square

Clara

AED 676 total

includes taxes & fees

13 Aug - 14 Aug

4. SpringHill Suites by Marriott Tarrytown Westchester County

11.2 km from Pleasant Square

Justin

AED 639 total

includes taxes & fees

10 Aug - 11 Aug

5. Westchester Marriott

11.7 km from Pleasant Square

Brygida

AED 703 total

includes taxes & fees

6 Aug - 7 Aug

6. Cambria Hotel & Suites - White Plains Downtown

16.5 km from Pleasant Square

Matthew

AED 770 total

includes taxes & fees

27 Aug - 28 Aug

Indoor pool, open 8:30 AM to 9:30 PM, sun loungers

7. DoubleTree by Hilton Hotel Nanuet

13.8 km from Pleasant Square

Paul

AED 522 total

includes taxes & fees

16 Aug - 17 Aug

8. The Abbey Inn & Spa

15.6 km from Pleasant Square

Izabella

AED 1,385 total

includes taxes & fees

30 Aug - 31 Aug

9. The Opus Westchester, Autograph Collection

16.4 km from Pleasant Square

Vann

AED 1,466 total

includes taxes & fees

3 Sep - 4 Sep

10. Baymont by Wyndham White Plains - Elmsford

10.9 km from Pleasant Square

Cason

AED 532 total

includes taxes & fees

23 Aug - 24 Aug

11. Sheraton Tarrytown Hotel

11.4 km from Pleasant Square

SANDRA

AED 602 total

includes taxes & fees

16 Aug - 17 Aug

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

14.4 km from Pleasant Square

David

AED 634 total

includes taxes & fees

2 Sep - 3 Sep

13. Hotel MTK Mount Kisco

13.2 km from Pleasant Square

Ellen

AED 617 total

includes taxes & fees

16 Aug - 17 Aug

14. Element by Marriott Spring Valley

14.8 km from Pleasant Square

Michael

AED 594 total

includes taxes & fees

16 Aug - 17 Aug

15. Tarrytown House Estate

12.5 km from Pleasant Square

Jennifer

AED 844 total

includes taxes & fees

30 Aug - 31 Aug

16. Sonesta White Plains Downtown

17 km from Pleasant Square

Sarah

AED 878 total

includes taxes & fees

16 Aug - 17 Aug

17. FairBridge Inn Express Nyack

9.8 km from Pleasant Square

Reign

AED 408 total

includes taxes & fees

9 Aug - 10 Aug

Standard Room, 1 King Bed | Premium bedding, desk, iron/ironing board, WiFi (free)

18. Ardsley Acres Hotel Westchester

17.1 km from Pleasant Square

Matthew

AED 515 total

includes taxes & fees

6 Aug - 7 Aug

19. Residence Inn by Marriott White Plains Westchester County

16.1 km from Pleasant Square

John

AED 807 total

includes taxes & fees

23 Aug - 24 Aug

20. Hampton Inn White Plains/Tarrytown

12 km from Pleasant Square

Dominique

AED 475 total

includes taxes & fees

16 Aug - 17 Aug

View all properties

Compare popular hotels close to Pleasant Square

Property	Property class	Guest rating
Windrose On Hudson	3.0 star property	8.6 Excellent 211 reviews	View
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG	2.5 star property	9.0 Wonderful 1,002 reviews	View
Courtyard by Marriott Tarrytown Westchester County	3.0 star property	9.0 Wonderful 1,001 reviews	View
SpringHill Suites by Marriott Tarrytown Westchester County	3.0 star property	8.8 Excellent 1,008 reviews	View
Westchester Marriott	4.5 star property	8.8 Excellent 611 reviews	View

Top Pleasant Square Hotel Reviews

Hotel Edison Times Square

10/10 Excellent

"Great location!! Hotel staff was very helpful."

ROW NYC

8/10 Good

"I am extremely disappointed with my experience regarding a refund issue. Making the reservation was quick and easy, but trying to get help after my stay has been incredibly frustrating. I was told to wait for the refund timeframe, and after more than 7 business days, I still had not received it. When I contacted the hotel for assistance, I was transferred between departments, including Accounting, but I had difficulty getting anyone to actually help or provide a clear update. I spent a significant amount of time trying to resolve an issue that should have been handled with better communication. The biggest frustration was not just the delay, but the lack of accountability and the amount of effort required from me to follow up on my own money. Customers should not have to chase departments and repeatedly explain the same issue after already waiting the required timeframe. I hope the hotel improves its customer service process, especially for billing and refund concerns. A smooth reservation process is important, but support after the payment is made is just as important."

Park Central Hotel New York

8/10 Good

"Overall, this is a very good hotel with a perfect location. I was very happy with my stay and really enjoyed my vacation. The staff were also wonderful. On our first day, we got stuck because the elevators were so crowded that we couldn't get down from the seventh floor. The housekeeping staff kindly let us use the service elevator, which we really appreciated. They were very friendly and helpful. However, the elevators were by far the biggest problem. If you're in a hurry, be prepared to wait. They were always crowded, stopped on almost every floor, and sometimes seemed to have technical issues. This is definitely something the hotel should improve. The Wi-Fi was another disappointment. It was very slow, and in the evenings it would sometimes stop working completely. The rooms were also quite noisy because of the street outside. However, since the hotel is located in the heart of New York City, that's somewhat understandable. Despite these issues, I would still recommend this hotel because the location is excellent and the staff were amazing. I just hope the management improves the elevator situation, as it was the biggest downside of our stay."

Highbridge Hotel

10/10 Excellent

"This my first time staying in the Bronx - we selected hotel because of it's proximity to Yankee Stadium. Hotel was clean, breakfast was good, staff was helpful and it was a 10 min walk to the stadium - our party of four was safe coming back to the hotel in the evening. In addition, this was close to the subway lines too - easy to get into and out of the Bronx on our trip to NYC"

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 family-friendly area.

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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 46 hotels and other accommodations within a few miles for a convenient home base.

Where is the best place to stay close to Pleasant Square?

Highbridge Hotel is one of the top choices for your stay based on our traveler data, and this hotel offers free breakfast and a fitness center. You'll find it 22.7 mi (36.5 km) from Pleasant Square. Other good options around the area include Night Hotel Broadway and Arthouse Hotel New York City.

How many hotels can I expect to find near Pleasant Square?

Expedia has 46 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. 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 Louis Engel Waterfront Park.

Find hotels near Pleasant Square, Ossining from AED 408

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Our top choices for Pleasant Square hotels

1. Windrose On Hudson

2. Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

3. Courtyard by Marriott Tarrytown Westchester County

4. SpringHill Suites by Marriott Tarrytown Westchester County

5. Westchester Marriott

6. Cambria Hotel & Suites - White Plains Downtown

7. DoubleTree by Hilton Hotel Nanuet

8. The Abbey Inn & Spa

9. The Opus Westchester, Autograph Collection

10. Baymont by Wyndham White Plains - Elmsford

11. Sheraton Tarrytown Hotel

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

13. Hotel MTK Mount Kisco

14. Element by Marriott Spring Valley

15. Tarrytown House Estate

16. Sonesta White Plains Downtown

17. FairBridge Inn Express Nyack

18. Ardsley Acres Hotel Westchester

19. Residence Inn by Marriott White Plains Westchester County

20. Hampton Inn White Plains/Tarrytown

Compare popular hotels close to Pleasant Square

Top Pleasant Square Hotel Reviews

Hotel Edison Times Square

Other attractions near Pleasant Square

Merchants Square

Frequently asked questions