Find hotels near Pleasant Square, Ossining from ₩99,416

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

Compare 8,485 hotels close to Pleasant Square with room rates, reviews, and availability. Most hotels are fully refundable.

Windrose On Hudson

2.0 star property
8.4 out of 10, Very Good, (9)
"Staying the historic former GE Crottonville training center. The place is amazing. It wasn’t intended to be a hotel per se. It is way, way more than that. I think it is still looking for its footing as a hotel/corporate conference training center for public, so being able to stay here feels like I have a 6 Sigma training with Neutron Jack at 8:AM. The place is something to see for yourself hurry!!"
The price is ₩302,012
₩336,364 total
includes taxes & fees
Aug 17 - Aug 18
Windrose On Hudson

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

2.5 star property
8.8 out of 10, Excellent, (847)
"the beds were very comfortable, "
The price is ₩274,431
₩313,881 total
includes taxes & fees
Aug 17 - Aug 18
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

Courtyard by Marriott Tarrytown Westchester County

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Nice hotel"
The price is ₩222,027
₩253,945 total
includes taxes & fees
Aug 24 - Aug 25
Courtyard by Marriott Tarrytown Westchester County

Days Inn by Wyndham Nanuet / Spring Valley

2.0 star property
6.8 out of 10, (1001)
"It was a wonderful stay at the hotel"
The price is ₩116,047
₩135,049 total
includes taxes & fees
Aug 17 - Aug 18
Days Inn by Wyndham Nanuet / Spring Valley

West Gate Inn Nyack

3.0 star property
7.4 out of 10, Good, (1005)
"Great place to stay I”ll recommend it "
The price is ₩136,512
₩156,136 total
includes taxes & fees
Aug 17 - Aug 18
West Gate Inn Nyack

Westchester Marriott

4.5 star property
8.8 out of 10, Excellent, (336)
"Great stay - would def stay there again!"
The price is ₩256,503
₩293,375 total
includes taxes & fees
Aug 24 - Aug 25
Westchester Marriott

Days Inn by Wyndham Elmsford / White Plains

2.0 star property
6.6 out of 10, (1002)
"Property is very quiet. Staff was very helpful. "
The price is ₩132,734
₩151,814 total
includes taxes & fees
Aug 24 - Aug 25
Days Inn by Wyndham Elmsford / White Plains

Inn on the Hudson

2.0 star property
6.8 out of 10, (1002)
"Good for a short stay, nice place, easy to and from train station"
The price is ₩157,212
₩179,815 total
includes taxes & fees
Aug 17 - Aug 18
Inn on the Hudson

SpringHill Suites by Marriott Tarrytown Westchester County

3.0 star property
8.4 out of 10, Very Good, (1005)
"Decent hotel."
The price is ₩221,544
₩253,392 total
includes taxes & fees
Aug 21 - Aug 22
SpringHill Suites by Marriott Tarrytown Westchester County

Baymont by Wyndham White Plains - Elmsford

2.5 star property
8.2 out of 10, Very Good, (1393)
"Super comfy bed breakfast was great "
The price is ₩198,101
₩226,576 total
includes taxes & fees
Aug 24 - Aug 25
Baymont by Wyndham White Plains - Elmsford

Extended Stay America Suites White Plains Elmsford

2.5 star property
6.8 out of 10, (1000)
"Good location . Clean and staff very friendly "
The price is ₩171,264
₩195,908 total
includes taxes & fees
Aug 17 - Aug 18
Extended Stay America Suites White Plains Elmsford

Sleepy Hollow Hotel

3.5 star property
6.6 out of 10, (1002)
"Great stay!"
The price is ₩241,610
₩276,343 total
includes taxes & fees
Sep 14 - Sep 15
Sleepy Hollow Hotel

Hampton Inn White Plains/Tarrytown

3.0 star property
8.0 out of 10, Very Good, (1106)
"Easy check in and breakfast was amazing"
The price is ₩174,657
₩199,764 total
includes taxes & fees
Sep 1 - Sep 2
Hampton Inn White Plains/Tarrytown

Hotel Nyack, a JdV by Hyatt Hotel

4.0 star property
8.6 out of 10, Excellent, (1002)
"The restaurant is farm to table and the food was excellent!"
The price is ₩136,526
₩193,510 total
includes taxes & fees
Aug 26 - Aug 27
Hotel Nyack, a JdV by Hyatt Hotel

FairBridge Inn Express Nyack

2.0 star property
7.6 out of 10, Good, (1000)
"Great place to stay! "
The price is ₩128,941
₩153,922 total
includes taxes & fees
Aug 21 - Aug 22
FairBridge Inn Express Nyack

Tappan Zee Hotel

2.0 star property
6.4 out of 10, (607)
"Good location, next to mall."
The price is ₩133,313
₩155,143 total
includes taxes & fees
Aug 15 - Aug 16
Tappan Zee Hotel

Quality Inn Spring Valley - Nanuet

2.5 star property
6.2 out of 10, (1001)
"bed was comfy, clean rooms"
The price is ₩117,895
₩137,200 total
includes taxes & fees
Sep 1 - Sep 2
Quality Inn Spring Valley - Nanuet

Armoni Inn & Suites

3.5 star property
6.0 out of 10, (1985)
"The area is very quiet and the pool is great also very great staff"
The price is ₩99,416
₩110,726 total
includes taxes & fees
Sep 2 - Sep 3
Armoni Inn & Suites

Sheraton Tarrytown Hotel

3.5 star property
8.2 out of 10, Very Good, (1002)
"Comfortable stay."
The price is ₩198,101
₩226,578 total
includes taxes & fees
Aug 24 - Aug 25
Sheraton Tarrytown Hotel

Motel 6 Elmsford, NY - White Plains

2.0 star property
6.4 out of 10, (826)
"We liked that it was quiet and clean."
The price is ₩150,316
₩171,926 total
includes taxes & fees
Aug 17 - Aug 18
Motel 6 Elmsford, NY - White Plains
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Pleasant Square Hotel Reviews

Hotels near Other Ossining Attractions

Hudson Hills Golf Course

Hudson Hills Golf Course

Enjoy a round of golf in Ossining at Hudson Hills Golf Course. Amble around this quaint area's riverfront and enjoy its top-notch restaurants.

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 35 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 (35.4 km) from Pleasant Square. Other good options around the area include Night Hotel Broadway and Sheraton New York Times Square Hotel.

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

Expedia has 35 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, Rockefeller State Park Preserve, or Rockland Lake State Park.