Top 10 Hotels Near 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

Andrew

P14,074 total

includes taxes & fees

Jun 30 - Jul 1

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

8.5 km from Pleasant Square

William

P9,398 total

includes taxes & fees

Jul 6 - Jul 7

3. Baymont by Wyndham White Plains - Elmsford

10.9 km from Pleasant Square

Jaime

P9,720 total

includes taxes & fees

Jul 12 - Jul 13

4. FairBridge Inn Express Nyack

9.8 km from Pleasant Square

Paige

P7,803 total

includes taxes & fees

Jul 5 - Jul 6

5. Tappan Zee Hotel

10.4 km from Pleasant Square

Mariya

P6,069 total

includes taxes & fees

Jun 27 - Jun 28

6. Hotel Nyack, a JdV by Hyatt Hotel

9.5 km from Pleasant Square

Jillian

P9,146 total

includes taxes & fees

Jul 14 - Jul 15

7. West Gate Inn Nyack

9.6 km from Pleasant Square

Gareth

P6,942 total

includes taxes & fees

Jul 19 - Jul 20

8. SpringHill Suites by Marriott Tarrytown Westchester County

11.2 km from Pleasant Square

Piper

P10,922 total

includes taxes & fees

Jul 26 - Jul 27

9. Hotel MTK Mount Kisco

13.2 km from Pleasant Square

Andrea

P10,869 total

includes taxes & fees

Jul 2 - Jul 3

10. Motel 6 Elmsford, NY - White Plains

12.2 km from Pleasant Square

Bruce

P9,503 total

includes taxes & fees

Jun 29 - Jun 30

11. Hampton Inn White Plains/Tarrytown

12 km from Pleasant Square

Dominique

P8,511 total

includes taxes & fees

Jul 27 - Jul 28

12. Tarrytown House Estate

12.5 km from Pleasant Square

Deanna

P11,400 total

includes taxes & fees

Jun 30 - Jul 1

Premium bedding, desk, blackout drapes, free WiFi

13. Quality Inn Spring Valley - Nanuet

15.2 km from Pleasant Square

Anna Lorraine

P7,706 total

includes taxes & fees

Jun 28 - Jun 29

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

14. DoubleTree by Hilton Hotel Nanuet

13.8 km from Pleasant Square

Norman

P8,985 total

includes taxes & fees

Jul 12 - Jul 13

15. Armoni Inn & Suites

14.6 km from Pleasant Square

Mohamed

P4,801 total

includes taxes & fees

Jun 30 - Jul 1

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

14.4 km from Pleasant Square

Jennifer

P10,380 total

includes taxes & fees

Jul 27 - Jul 28

17. Days Inn by Wyndham Elmsford / White Plains

12.4 km from Pleasant Square

Mark

P8,069 total

includes taxes & fees

Jul 26 - Jul 27

18. Budget Motor Inn - Stony Point

12.3 km from Pleasant Square

Tariq

P4,249 total

includes taxes & fees

Jun 30 - Jul 1

19. Sonesta Simply Suites Nanuet

15.1 km from Pleasant Square

Delilah

P8,007 total

includes taxes & fees

Jul 12 - Jul 13

20. Cambria Hotel & Suites - White Plains Downtown

16.5 km from Pleasant Square

Sean

P14,247 total

includes taxes & fees

Jul 26 - Jul 27

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 174 reviews	View
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG	2.5 star property	9.0 Wonderful 1,002 reviews	View
Baymont by Wyndham White Plains - Elmsford	2.5 star property	8.4 Very Good 1,719 reviews	View
FairBridge Inn Express Nyack	2.0 star property	7.8 Good 1,000 reviews	View
Tappan Zee Hotel	2.0 star property	6.4 677 reviews	View

Top Pleasant Square Hotel Reviews

Sheraton New York Times Square Hotel

8/10 Good

"The room was mostly clean but I did find several hairs on the bathroom counter. The room had the thinnest, smallest dresser drawers I have ever seen. A single sweatshirt couldn't fit in one drawer. Overall clean but older and very small. My biggest problem was the constant fees. Resort fees were almost $40 per day. This is not a resort, no one stays on the property because it's NYC. However, I received a $35 per day credit for the restaurants and coffee shop. I used it for dinner at the bar/restaurant that the coffee shop turns into at 5 pm every day. It was good. I used it the next day at the breakfast buffet. The buffet was $47 with tip and tax included. It was literally the worst breakfast buffet I have ever had. The pre-made Belgian waffle was like cardboard but tasted worse. I literally spit it out. The eggs and potatoes were cold. The best part was the Fruit Loops. I paid $47 for Fruit Loops. The biggest surprise was the $6 per item for them to hold your bags if you aren't leaving for the airport yet, or are arriving prior to the room being ready. I saw kids stuffing their skateboards into their luggage, or it would be $6. One family of 4 had to consolidate 8 items into 4 items. I have never paid for a hotel to hold my luggage, ever. The best thing I can say about the hotel is the location. It's north of Times Square, so the sidewalks aren't crazy, and it was within a couple of blocks from numerous diners and restaurants. 6 short blocks from Central Park. Safe area."

Hyatt Regency Times Square

10/10 Excellent

"World Class hotel in prime location. We rented a corner room overlooking Times Square. Hotel was well staffed with World Cup events filling the hotel with multiple large groups. We were in town for a family trip to see several Broadway shows. All the theaters we attended were within walking distance of the theaters. And as a bonus, we were able to attend the street market on 8th Avenue on Sunday."

Hampton Inn New York Times Square

10/10 Excellent

"This is a great location right off of Times Square. You can walk to almost everything mid town and Broadway shows. Good breakfast. They have a desk there to help with ground transport back to the New York Airports. Plenty of food options right out the door from upscale to food stands. The rooms are a bit small, but you are in NY not a resort. Will book again when back in NY."

Hotels near other Pleasant Square attractions

Merchants Square

9.0/5 (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 quaint 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?

Night Hotel Broadway is one of the top choices for your stay based on our traveler data, and this hotel offers free WiFi and laundry facilities. You'll find it 26.1 mi (42.1 km) from Pleasant Square. Other good options around the area include Hotel Belleclaire and Empire Hotel.

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.

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 Merchants Square.

Hotels near Pleasant Square

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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. Baymont by Wyndham White Plains - Elmsford

4. FairBridge Inn Express Nyack

5. Tappan Zee Hotel

6. Hotel Nyack, a JdV by Hyatt Hotel

7. West Gate Inn Nyack

8. SpringHill Suites by Marriott Tarrytown Westchester County

9. Hotel MTK Mount Kisco

10. Motel 6 Elmsford, NY - White Plains

11. Hampton Inn White Plains/Tarrytown

12. Tarrytown House Estate

13. Quality Inn Spring Valley - Nanuet

14. DoubleTree by Hilton Hotel Nanuet

15. Armoni Inn & Suites

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

17. Days Inn by Wyndham Elmsford / White Plains

18. Budget Motor Inn - Stony Point

19. Sonesta Simply Suites Nanuet

20. Cambria Hotel & Suites - White Plains Downtown

Compare popular hotels close to Pleasant Square

Top Pleasant Square Hotel Reviews

Sheraton New York Times Square Hotel

Hotels near other Pleasant Square attractions

Merchants Square

Frequently asked questions