The Best Hotels Closest to Pleasant Square in Ossining for 2026

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Our top choices for Pleasant Square hotels

1. Windrose On Hudson

3.1 km from Pleasant Square

Rachel

NT$5,872

NT$6,540 total

includes taxes & fees

Sep 27 - Sep 28

2. Cambria Hotel & Suites - White Plains Downtown

16.5 km from Pleasant Square

Matthew

NT$6,409

NT$7,331 total

includes taxes & fees

Sep 27 - Sep 28

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

8.5 km from Pleasant Square

Wanda

NT$4,873

NT$5,574 total

includes taxes & fees

Sep 13 - Sep 14

4. Ardsley Acres Hotel Westchester

17.1 km from Pleasant Square

Calvern

NT$3,541

NT$4,050 total

includes taxes & fees

Sep 17 - Sep 18

5. HYATT house White Plains

19.6 km from Pleasant Square

Lynn

NT$6,152

NT$7,037 total

includes taxes & fees

Sep 27 - Sep 28

6. Sheraton Tarrytown Hotel

11.4 km from Pleasant Square

Desorene

NT$5,275

NT$6,033 total

includes taxes & fees

Sep 20 - Sep 21

7. Baymont by Wyndham White Plains - Elmsford

10.9 km from Pleasant Square

Ebony

NT$3,996

NT$4,570 total

includes taxes & fees

Sep 20 - Sep 21

8. Element by Marriott Spring Valley

14.8 km from Pleasant Square

Yocheved

NT$4,228

NT$4,920 total

includes taxes & fees

Sep 27 - Sep 28

9. West Gate Inn Nyack

9.6 km from Pleasant Square

Marcelo

NT$3,132

NT$3,583 total

includes taxes & fees

Sep 13 - Sep 14

10. Days Inn by Wyndham Elmsford / White Plains

12.4 km from Pleasant Square

Frankie

NT$3,363

NT$3,957 total

includes taxes & fees

Sep 20 - Sep 21

11. Sonesta Simply Suites Nanuet

15.1 km from Pleasant Square

EDWARD

NT$3,248

NT$3,780 total

includes taxes & fees

Sep 20 - Sep 21

12. DoubleTree by Hilton Hotel Nanuet

13.8 km from Pleasant Square

Linda

NT$3,984

NT$4,637 total

includes taxes & fees

Sep 23 - Sep 24

13. Hampton Inn White Plains/Tarrytown

12 km from Pleasant Square

Susan

NT$3,725

NT$4,261 total

includes taxes & fees

Sep 20 - Sep 21

14. Hilton Garden Inn Westchester Dobbs Ferry, NY

17.7 km from Pleasant Square

Jean

NT$4,800

NT$5,490 total

includes taxes & fees

Oct 5 - Oct 6

15. Hilton Garden Inn Nanuet

15.2 km from Pleasant Square

cole

NT$3,737

NT$4,348 total

includes taxes & fees

Oct 5 - Oct 6

16. Inn on the Hudson

15.3 km from Pleasant Square

Sean

NT$3,439

NT$3,933 total

includes taxes & fees

Sep 13 - Sep 14

17. Motel 6 Elmsford, NY - White Plains

12.2 km from Pleasant Square

"The bed was really nice and it was easy to park. The parking lot was very noisy, with people playing music loudly in their cars for hours on end (both at night and in the morning). The room was good, with a nice big desk to get work done, but the floor was dirty and for sure had not been vacuumed/sweeped before we checked in. The shower was a bit of a hazard because the knob got insanely hot once turned on. The AC worked great, but I didn't like that I couldn't change the direction of the...

Estela

NT$3,521

NT$4,027 total

includes taxes & fees

Sep 21 - Sep 22

18. Extended Stay America Suites White Plains Elmsford

12 km from Pleasant Square

Debbie

NT$3,691

NT$4,222 total

includes taxes & fees

Sep 13 - Sep 14

19. Tappan Zee Hotel

10.4 km from Pleasant Square

Bayron

NT$2,684

NT$3,123 total

includes taxes & fees

Sep 13 - Sep 14

20. Days Inn by Wyndham Nanuet / Spring Valley

15.4 km from Pleasant Square

Jason L

NT$3,191

NT$3,714 total

includes taxes & fees

Sep 16 - Sep 17

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Compare popular hotels close to Pleasant Square

Property	Property class	Guest rating
Windrose On Hudson	8.6 Excellent 239 reviews	View
Cambria Hotel & Suites - White Plains Downtown	9.4 Exceptional 1,001 reviews	View
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG	9.0 Wonderful 1,002 reviews	View
Ardsley Acres Hotel Westchester	8.8 Excellent 1,155 reviews	View
HYATT house White Plains	8.8 Excellent 1,175 reviews	View

Top Pleasant Square Hotel Reviews

Motto By Hilton New York City Times Square

10/10 Excellent

"⭐️⭐️⭐️⭐️⭐️"

Hilton Garden Inn New York/Central Park South-Midtown West

8/10 Good

"Room was new and clean"

Hotel Edison Times Square

8/10 Good

"Convenient location"

Night Hotel Broadway

8/10 Good

"The highest tier room was very clean, but also very sparse."

ROW NYC

10/10 Excellent

"It was"

Harmony Suites

10/10 Excellent

"I came to attend the Chris Brown and Usher concert. Loved the hotel! It reminded me of a coliseum."

Hotel Belleclaire Central Park, a Small Luxury Hotel

10/10 Excellent

"Hotel Belleclaire is a beautiful very clean and well located hotel! The staff is eager to help with all your needs. The beds and linen were perfect and the free breakfast was nice. I only wish they had some more GF options. I have stayed here before and will book my next trip here again! Thank you for making us feel comfortable, safe and at home!"

Ameritania Hotel at Times Square

8/10 Good

"The location was perfect. Check-in was rough, but once we got checked in, we had a nice stay. The room was clean and comfortable. The lobby furniture is worn, ripped, and old. The doormen and manager were great, very helpful, and friendly!"

Warwick New York

8/10 Good

"Nice room. Very conveniently located to Rockefeller center, Central Park, Broadway and Time Square. The only minus that the room had scaffolding right outside the window so no views and made the room a bit dark."

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.

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Sing Sing Prison Museum

You can spend time browsing the exhibits at Sing Sing Prison Museum during your travels in Ossining. Amble around this family-friendly area's riverfront and enjoy its top-notch restaurants.

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Ossining Public Library

Learn about the local history of Ossining when you spend time at Ossining Public Library. Amble around the area's parks or visit its monuments.

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Snowden Avenue Park

Snowden Avenue Park is just one of the places to see in Ossining, so why not enjoy the other things to explore during your travels? Stroll along the riverfront in this family-friendly area, or check out its top-notch restaurants.

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Depot Square

Explore the great outdoors at Depot Square, a lovely green space in Ossining. Stroll along the riverfront or attend a sporting event in this quaint area.

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Nelson Park

Nelson Park is just one of the places to see in Ossining, so why not enjoy the other things to explore during your travels? Stroll along the riverfront in this quaint area, or check out its top-notch restaurants.

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Crawbuckie Park

Explore the great outdoors at Crawbuckie Park, a lovely green space in Ossining. Amble around the area's parks or visit its monuments.

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Louis Engel Waterfront Park

Louis Engel Waterfront Park is just one of the places to see in Ossining, so why not enjoy the other things to explore during your travels? Amble around this quaint area's riverfront and enjoy its top-notch restaurants.

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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?

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 Highbridge Hotel and Night Hotel Broadway.

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 Merchants Square.

Find hotels near Pleasant Square, Ossining from NT$3,123

Change your mind

Treat yourself

Be picky

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Our top choices for Pleasant Square hotels

1. Windrose On Hudson

2. Cambria Hotel & Suites - White Plains Downtown

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

4. Ardsley Acres Hotel Westchester

5. HYATT house White Plains

6. Sheraton Tarrytown Hotel

7. Baymont by Wyndham White Plains - Elmsford

8. Element by Marriott Spring Valley

9. West Gate Inn Nyack

10. Days Inn by Wyndham Elmsford / White Plains

11. Sonesta Simply Suites Nanuet

12. DoubleTree by Hilton Hotel Nanuet

13. Hampton Inn White Plains/Tarrytown

14. Hilton Garden Inn Westchester Dobbs Ferry, NY

15. Hilton Garden Inn Nanuet

16. Inn on the Hudson

17. Motel 6 Elmsford, NY - White Plains

18. Extended Stay America Suites White Plains Elmsford

19. Tappan Zee Hotel

20. Days Inn by Wyndham Nanuet / Spring Valley

Compare popular hotels close to Pleasant Square

Top Pleasant Square Hotel Reviews

Motto By Hilton New York City Times Square

Hilton Garden Inn New York/Central Park South-Midtown West

Hotel Edison Times Square

Night Hotel Broadway

ROW NYC

Harmony Suites

Hotel Belleclaire Central Park, a Small Luxury Hotel

Ameritania Hotel at Times Square

Warwick New York

Other attractions near Pleasant Square

Merchants Square

Sing Sing Prison Museum

Ossining Public Library

Snowden Avenue Park

Depot Square

Nelson Park

Crawbuckie Park

Louis Engel Waterfront Park

Frequently asked questions

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