The Best Hotels Closest to Pleasant Square in Ossining - 2026 Updated Prices

Our top choices for Pleasant Square hotels

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

8.5 km from Pleasant Square

Casey

4.364.844 ₫ total

includes taxes & fees

7 Jun - 8 Jun

Baymont by Wyndham White Plains - Elmsford

10.9 km from Pleasant Square

Wynona

4.307.644 ₫ total

includes taxes & fees

7 Jun - 8 Jun

Hotel Nyack, a JdV by Hyatt Hotel

9.5 km from Pleasant Square

JOSE

4.249.275 ₫ total

includes taxes & fees

8 Jun - 9 Jun

FairBridge Inn Express Nyack

9.8 km from Pleasant Square

Suruba

3.110.412 ₫ total

includes taxes & fees

1 Jul - 2 Jul

West Gate Inn Nyack

9.6 km from Pleasant Square

Edmund

2.979.837 ₫ total

includes taxes & fees

3 Jun - 4 Jun

Courtyard by Marriott Tarrytown Westchester County

10.9 km from Pleasant Square

Brian

5.358.218 ₫ total

includes taxes & fees

18 Jun - 19 Jun

SpringHill Suites by Marriott Tarrytown Westchester County

11.2 km from Pleasant Square

Piper

4.949.729 ₫ total

includes taxes & fees

7 Jun - 8 Jun

Tappan Zee Hotel

10.4 km from Pleasant Square

Mariya

1.916.376 ₫ total

includes taxes & fees

15 Jun - 16 Jun

Tarrytown House Estate

12.5 km from Pleasant Square

Deanna

5.691.484 ₫ total

includes taxes & fees

16 Jun - 17 Jun

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

DoubleTree by Hilton Hotel Nanuet

13.8 km from Pleasant Square

Thomas

4.058.919 ₫ total

includes taxes & fees

7 Jun - 8 Jun

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

14.4 km from Pleasant Square

Jennifer

4.996.991 ₫ total

includes taxes & fees

7 Jun - 8 Jun

Westchester Marriott

11.7 km from Pleasant Square

Leneir

6.742.927 ₫ total

includes taxes & fees

21 Jun - 22 Jun

Hampton Inn White Plains/Tarrytown

12 km from Pleasant Square

Minerva

4.203.793 ₫ total

includes taxes & fees

14 Jun - 15 Jun

Sheraton Tarrytown Hotel

11.4 km from Pleasant Square

Ciaran

4.834.841 ₫ total

includes taxes & fees

18 Jun - 19 Jun

Hotel MTK Mount Kisco

13.2 km from Pleasant Square

Heidi

4.664.202 ₫ total

includes taxes & fees

29 Jun - 30 Jun

Motel 6 Elmsford, NY - White Plains

12.2 km from Pleasant Square

Bruce

3.492.005 ₫ total

includes taxes & fees

3 Jun - 4 Jun

Armoni Inn & Suites

14.6 km from Pleasant Square

Mohamed

2.523.729 ₫ total

includes taxes & fees

9 Jun - 10 Jun

Premium bedding, desk, blackout curtains, free WiFi

Quality Inn Spring Valley - Nanuet

15.2 km from Pleasant Square

Anna Lorraine

3.306.842 ₫ total

includes taxes & fees

8 Jun - 9 Jun

Cambria Hotel & Suites - White Plains Downtown

16.5 km from Pleasant Square

Zoran Dragutin

5.859.423 ₫ total

includes taxes & fees

28 Jun - 29 Jun

Sleepy Hollow Hotel, a Dolce by Wyndham

11.3 km from Pleasant Square

Morgan

4.729.984 ₫ total

includes taxes & fees

16 Jun - 17 Jun

View all properties

Compare popular hotels close to Pleasant Square

Property	Property class	Guest rating
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG	2.5 star property	9.0 Wonderful 1,004 reviews	View
Baymont by Wyndham White Plains - Elmsford	2.5 star property	8.4 Very good 1,701 reviews	View
Hotel Nyack, a JdV by Hyatt Hotel	4.0 star property	8.6 Excellent 1,124 reviews	View
FairBridge Inn Express Nyack	2.0 star property	7.8 Good 1,001 reviews	View
West Gate Inn Nyack	3.0 star property	7.2 Good 1,313 reviews	View

Top Pleasant Square Hotel Reviews

Hyatt Grand Central New York

6/10 Okay

"Good location but the facility is old and not clean."

Night Hotel Broadway

8/10 Good

"Night Hotel is a convenient & budget friendly option. The staff is very nice. There are updated rooms & old school rooms which are comfortable & clean, but shabby. If you are on a budget & like the UWS, this hotel is just fine. I find it quiet and clean and the staff is nice. If you get a room that hasn’t been updated, just focus on the clean bathroom, comfortable bed and peace & quiet. I find the rooms rather roomy for NYC as well."

Paramount Times Square – A Generator Hotel

8/10 Good

"Great location if you want to be steps away from time square. Can be noisy at night if you like to go to bed early. We didn’t mind the noise outside. We could hear the neighbors through the joining room. That was a bit annoying. The staff was helpful when we called but no one made up our room the whole stay. Not sure if you need to ask or not. The rooms are a little out dated, but they were clean. Overall a decent place. I would stay there again."

Park Central Hotel New York

2/10 Terrible

"I like nothing it was a horrible experience I’ve stayed in better rooms at a motel 6 , we had to carry our bags 3 blocks just to get to the hotel , the room was old and run down , beds were not comfortable , had no iron or refrigerator or microwave , for the price we paid was not justified, being downtown New York City you have to do better , what was suppose to once in life time experience was horrible stay"

M Social Hotel New York Times Square

2/10 Terrible

"Patio was out of function so you could not sit outside to explore the view. That was the reason I booked. The room was EXTREMELY cold, & I mean COLD for the month of June. Heater apparently is out of function spring onwards. We asked for a mini heater which was not available. Did not get to sleep at all."

The Manhattan at Times Square

4/10 Poor

"The hotel is in an excellent location and the front desk staff, porters, etc were amazing. Unfortunately, the website is showing the hotel will be or is in the process of being renovated to a Crowne Plaza. I generally do not leave reviews, and have never left a poor one, but the rooms are in extremely poor repair. Obviously no effort is being made until the complete reno. Rusty sink, yucky bathtub with the ceiling in shambles because no fan in bathroom, rugs dirty and do not look vaccumed, furniture old and scraped up, and no plugs by bed or desk! Even photo on wall, is hanging down inside the class, bathroom mirror cracked and light fixure hanging crooked. Would never step in bare feet here. So that’s where it stands in the meantime, but I’m sure will be amazing once renovated!"

Hotels near other Pleasant Square attractions

Merchants Square

4.5/5 (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 43 hotels and other accommodations within a few miles for a convenient home base.

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

Expedia has 43 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 Ossining Historical Society and Sing Sing Prison Museum. 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 Rockwood Hall Park.

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Our top choices for Pleasant Square hotels

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

Baymont by Wyndham White Plains - Elmsford

Hotel Nyack, a JdV by Hyatt Hotel

FairBridge Inn Express Nyack

West Gate Inn Nyack

Courtyard by Marriott Tarrytown Westchester County

SpringHill Suites by Marriott Tarrytown Westchester County

Tappan Zee Hotel

Tarrytown House Estate

DoubleTree by Hilton Hotel Nanuet

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

Westchester Marriott

Hampton Inn White Plains/Tarrytown

Sheraton Tarrytown Hotel

Hotel MTK Mount Kisco

Motel 6 Elmsford, NY - White Plains

Armoni Inn & Suites

Quality Inn Spring Valley - Nanuet

Cambria Hotel & Suites - White Plains Downtown

Sleepy Hollow Hotel, a Dolce by Wyndham

Compare popular hotels close to Pleasant Square

Top Pleasant Square Hotel Reviews

Hyatt Grand Central New York

Hotels near other Pleasant Square attractions

Merchants Square

Frequently asked questions

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