The Best Hotels Closest to Pleasant Square in Ossining for 2026

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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

3.1 km from Pleasant Square

Michael

SAR 687 total

includes taxes & fees

15 Nov - 16 Nov

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

0.7 km from Pleasant Square

SAR 3,958 total

includes taxes & fees

16 Nov - 17 Nov

An indoor swimming pool with clear water, sunroof, and lounge chairs.

3. DoubleTree by Hilton Hotel Nanuet

13.8 km from Pleasant Square

Joel

SAR 553 total

includes taxes & fees

6 Dec - 7 Dec

An outdoor seating area with wicker chairs and tables, surrounded by greenery and a modern lamp structure.

4. Westchester Marriott

11.7 km from Pleasant Square

Karrie

SAR 769 total

includes taxes & fees

22 Nov - 23 Nov

A modern hotel lobby with a kitchen area, seating arrangements, and large windows offering a view of the outdoors.

5. Baymont by Wyndham White Plains - Elmsford

10.9 km from Pleasant Square

Omari

SAR 577 total

includes taxes & fees

29 Nov - 30 Nov

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

11.2 km from Pleasant Square

Gwen

SAR 669 total

includes taxes & fees

15 Nov - 16 Nov

A modern reception area with a wooden reception desk, a blue accent wall, and a large glass door leading to an outdoor seating area.

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

8.5 km from Pleasant Square

Sean P.

SAR 558 total

includes taxes & fees

10 Dec - 11 Dec

A hotel room with a wooden headboard, a bedside table with a lamp, and a bed with white bedding and pillows.

8. Ardsley Acres Hotel Westchester

17.1 km from Pleasant Square

Wendell

SAR 531 total

includes taxes & fees

19 Nov - 20 Nov

A modern lounge with leather sofas, a patterned rug, and red pendant lights.

9. Hotel Nyack, a JdV by Hyatt Hotel

9.5 km from Pleasant Square

Kristen

SAR 608 total

includes taxes & fees

22 Nov - 23 Nov

A spacious hotel lobby with a modern design, featuring a large seating area, a dining table, and large windows providing views of the outdoors.

10. Element by Marriott Spring Valley

14.8 km from Pleasant Square

Rohan

SAR 585 total

includes taxes & fees

22 Nov - 23 Nov

A modern kitchen with a central island, bar stools, a fireplace, and a contemporary pendant light.

11. Courtyard by Marriott Tarrytown Westchester County

10.9 km from Pleasant Square

Syble

SAR 653 total

includes taxes & fees

19 Nov - 20 Nov

A spacious lobby with a reception desk, sofas, and a coffee table. There are multiple seating areas and a large window providing natural light.

12. Sheraton Tarrytown Hotel

11.4 km from Pleasant Square

Jiamin

SAR 580 total

includes taxes & fees

22 Nov - 23 Nov

A modern lobby with seating areas, a fireplace, and a flat-screen TV mounted on the wall.

13. Cambria Hotel & Suites - White Plains Downtown

16.5 km from Pleasant Square

Anthony

SAR 821 total

includes taxes & fees

6 Dec - 7 Dec

A hotel patio with outdoor seating, a fire pit, and a covered area with glass doors.

14. Residence Inn Orangeburg

15.4 km from Pleasant Square

Jessica

SAR 598 total

includes taxes & fees

29 Nov - 30 Nov

An indoor swimming pool with clear water, surrounded by lounge chairs and a seating area.

15. Sonesta White Plains Downtown

17 km from Pleasant Square

Laura

SAR 837 total

includes taxes & fees

22 Nov - 23 Nov

A modern kitchen with a large island, bar stools, a flat-screen TV, and a stone backsplash.

16. Hampton Inn White Plains/Tarrytown

12 km from Pleasant Square

Michelle

SAR 486 total

includes taxes & fees

22 Nov - 23 Nov

A Holiday Inn Express & Suites sign with a bench and flower beds in front.

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

14.4 km from Pleasant Square

John

SAR 562 total

includes taxes & fees

22 Nov - 23 Nov

A large, historic building with a prominent tower, surrounded by well-maintained gardens and a parking area.

18. The Abbey Inn & Spa

15.6 km from Pleasant Square

Lina

SAR 1,519 total

includes taxes & fees

6 Dec - 7 Dec

A spacious lobby with a red sofa, green armchairs, a fireplace, and a staircase leading to an upper level.

19. Hotel MTK Mount Kisco

13.2 km from Pleasant Square

Joseph

SAR 630 total

includes taxes & fees

16 Nov - 17 Nov

A breakfast area with multiple tables and chairs, a kitchen area with appliances, and a sign for Daybreak Breakfast.

20. Days Inn by Wyndham Elmsford / White Plains

12.4 km from Pleasant Square

Peter

SAR 461 total

includes taxes & fees

29 Nov - 30 Nov

View all properties

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

Top Pleasant Square Hotel Reviews

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

Hawthorne

10/10 Excellent

Lorena

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

Peekskill

10/10 Excellent

David Allen

Westchester Marriott

Tarrytown

10/10 Excellent

This hotel was nice, the only thing I was not a big fan of was the overcrowded lobby. I felt like it was a hassle to enter and exit the doors because people were permitted to block doorways and the main hallway to get to the elevators. I understand people are eager to congregate, but a kind reminder to move over for guests just trying to get up to their rooms by staff would have made the experience much more welcoming.

KELLY

SpringHill Suites by Marriott Tarrytown Westchester County

Tarrytown

10/10 Excellent

James

Cambria Hotel & Suites - White Plains Downtown

White Plains

10/10 Excellent

Keeping in mind its 3-star classification, this hotel does not disappoint. Front desk staff is outstanding. Metro-North station is in easy walking distance. Of special note: In partnership with the Chazz Palminteri restaurant next door, guests can order a meal, get it delivered and charged to the room. Very nice option when traveling all day. On a lesser note, the slamming doors made a lot of disruption. Soft close, as in other hotels, would improve the guest experience and be worth the...

William

A modern hotel entrance with a glass door, a car parked outside, and a well-lit pathway leading to the entrance.

The Opus Westchester, Autograph Collection

White Plains

10/10 Excellent

Anonymous traveler

Hotel Nyack, a JdV by Hyatt Hotel

Nyack

10/10 Excellent

JASON

Sonesta White Plains Downtown

White Plains

10/10 Excellent

Amy

Ardsley Acres Hotel Westchester

Ardsley

10/10 Excellent

Valerie

Sheraton Tarrytown Hotel

Tarrytown

10/10 Excellent

Jason

Baymont by Wyndham White Plains - Elmsford

Elmsford

10/10 Excellent

Norma Jean

Hotel MTK Mount Kisco

Mount Kisco

10/10 Excellent

Overall our stay at MTK was very positive. Generally staff was responsive and friendly but not our experience in the restaurant. Service person barely greeted us, sat looking at his phone, apparently not checking on our food for which we waited a very long time. He made it quite clear that he did not enjoy his job and did not want to be there. However, we definitely would stay at MTK again without hesitation.

Shirley

A modern high-rise hotel with a curved facade, multiple floors, and a well-lit entrance.

Residence Inn by Marriott White Plains Westchester County

White Plains

10/10 Excellent

The receptionist was awesome, professional, and really connects with us, very positive, courteous, informative, and shows a lot of customer care, great service. The corner suite was pretty awesome spacious, and felt like I was in a new home or an apartment. Very clean. I would recommend the suites , especially with the kitchen for multiple nights and long stays. I've been to the Chinese restaurant, and it's got awesome dim sum, and pretty authentic. Everything else you want is local and a few...

Anonymous traveler

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.

Find hotels near Pleasant Square, Ossining from SAR 442

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Our top choices for Pleasant Square hotels

1. Windrose On Hudson

2. Summer Pool Oasis Custom Bar Arcade Pool Table

3. DoubleTree by Hilton Hotel Nanuet

4. Westchester Marriott

5. Baymont by Wyndham White Plains - Elmsford

6. SpringHill Suites by Marriott Tarrytown Westchester County

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

8. Ardsley Acres Hotel Westchester

9. Hotel Nyack, a JdV by Hyatt Hotel

10. Element by Marriott Spring Valley

11. Courtyard by Marriott Tarrytown Westchester County

12. Sheraton Tarrytown Hotel

13. Cambria Hotel & Suites - White Plains Downtown

14. Residence Inn Orangeburg

15. Sonesta White Plains Downtown

16. Hampton Inn White Plains/Tarrytown

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

18. The Abbey Inn & Spa

19. Hotel MTK Mount Kisco

20. Days Inn by Wyndham Elmsford / White Plains

Other attractions near Pleasant Square

Merchants Square

Top Pleasant Square Hotel Reviews

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

10/10 Excellent

Frequently Asked Questions

What's the area like around Pleasant Square?

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

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

If I need to cancel the hotel reservation for my stay near Pleasant Square, will I receive a refund?

Where can I learn more about changing or cancelling my trip in the area near Pleasant Square?

What can I see and do near Pleasant Square?