Find hotels near Pleasant Square, Ossining from $82

  • Upfront pricing

    Our total price for your stay includes taxes and fees
  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Pleasant Square hotels

Windrose On Hudson

Windrose On Hudson
3.0 star property
1.9 mi from Pleasant Square
8.4 out of 10, Very Good, (127 reviews)
"Room was clean, super quiet, staff was very helpful and nice"
United States
Dawn
$172 nightly
The price is $191
May 3 - May 4
Total with taxes and fees
Windrose On Hudson

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
2.5 star property
5.3 mi from Pleasant Square
9.0 out of 10, Wonderful, (1,004 reviews)
"Very Clean and spacious we loved our stay "
United States
Maria
$139 nightly
The price is $159
Apr 26 - Apr 27
Total with taxes and fees
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

Hotel Nyack, a JdV by Hyatt Hotel

Hotel Nyack, a JdV by Hyatt Hotel
4.0 star property
5.9 mi from Pleasant Square
8.6 out of 10, Excellent, (1,050 reviews)
"excellent stay!"
United States
Karen
$110 nightly
The price is $126
Apr 27 - Apr 28
Total with taxes and fees
Hotel Nyack, a JdV by Hyatt Hotel

West Gate Inn Nyack

West Gate Inn Nyack
3.0 star property
5.9 mi from Pleasant Square
7.4 out of 10, Good, (1,252 reviews)
"The front staff Stu, Andre, Stephanie are all so professional and helpful. This place is an amazing place to stay! Breakfast is a plus!"
United States
Joseph
$88 nightly
The price is $101
Apr 30 - May 1
Total with taxes and fees
West Gate Inn Nyack

FairBridge Inn Express Nyack

FairBridge Inn Express Nyack
2.0 star property
6.1 mi from Pleasant Square
7.8 out of 10, Good, (1,001 reviews)
"Quiet ok place to stay "
United States
Luis
$85 nightly
The price is $102
May 6 - May 7
Total with taxes and fees
FairBridge Inn Express Nyack

Courtyard by Marriott Tarrytown Westchester County

Courtyard by Marriott Tarrytown Westchester County
3.0 star property
6.8 mi from Pleasant Square
9.0 out of 10, Wonderful, (1,002 reviews)
"McKenzie, at the front desk, is amazing and made the stay perfect. Thanks!"
United States
camie
$159 nightly
The price is $182
Apr 26 - Apr 27
Total with taxes and fees
Courtyard by Marriott Tarrytown Westchester County

SpringHill Suites by Marriott Tarrytown Westchester County

SpringHill Suites by Marriott Tarrytown Westchester County
3.0 star property
6.9 mi from Pleasant Square
8.6 out of 10, Excellent, (1,001 reviews)
"Nice place to stay"
United States
Kerri
$126 nightly
The price is $144
Apr 26 - Apr 27
Total with taxes and fees
SpringHill Suites by Marriott Tarrytown Westchester County

Westchester Marriott

Westchester Marriott
4.5 star property
7.3 mi from Pleasant Square
8.8 out of 10, Excellent, (525 reviews)
"This hotel was great and noticeably a level above other available properties. Had one of the best night's sleep here I'm not sure if their mattresses are different but these are extremely comfortable rooms and the property is very well kept a model example for other hotels and the chain"
United States
william
$206 nightly
The price is $236
Apr 23 - Apr 24
Total with taxes and fees
Westchester Marriott

Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford
2.5 star property
6.7 mi from Pleasant Square
8.2 out of 10, Very Good, (1,661 reviews)
"Very nice place"
United States
Romane
$122 nightly
The price is $140
Apr 19 - Apr 20
Total with taxes and fees
Baymont by Wyndham White Plains - Elmsford

Tappan Zee Hotel

Tappan Zee Hotel
2.0 star property
6.5 mi from Pleasant Square
6.4 out of 10, (659 reviews)
"Parking spacious Mall convenient Price affordable "
United States
dalia
$90 nightly
The price is $105
Apr 19 - Apr 20
Total with taxes and fees
Tappan Zee Hotel

Tarrytown House Estate

Tarrytown House Estate
3.5 star property
7.8 mi from Pleasant Square
8.2 out of 10, Very Good, (1,044 reviews)
"Lovely property and staff!"
United States
Gray
$174 nightly
The price is $199
Apr 19 - Apr 20
Total with taxes and fees
Tarrytown House Estate

Motel 6 Elmsford, NY - White Plains

Motel 6 Elmsford, NY - White Plains
2.0 star property
7.6 mi from Pleasant Square
6.6 out of 10, (956 reviews)
"Staff was beyond rude, room smelled and bedsheets had holes"
United States
RICHARD
$99 nightly
The price is $113
Apr 19 - Apr 20
Total with taxes and fees
Motel 6 Elmsford, NY - White Plains

Sheraton Tarrytown Hotel

Sheraton Tarrytown Hotel
3.5 star property
7.1 mi from Pleasant Square
8.4 out of 10, Very Good, (1,000 reviews)
"I enjoyed my stay rooms are very clean comfortable bed pool and hot was good also buffet was breakfast was good staff very nice check in was easy and fast "
United States
Florence
$144 nightly
The price is $164
Apr 30 - May 1
Total with taxes and fees
Sheraton Tarrytown Hotel

Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown
3.0 star property
7.4 mi from Pleasant Square
8.0 out of 10, Very Good, (1,401 reviews)
"Perfect location right off Highway and inly 45 minutes to JFK. Friendly staff, decent breakfast and the coffee and cookies hit the spot when we arrived! Room was clean and perfect for our one night stay. Would absolutely stay there again. "
United States
Gordon
$130 nightly
The price is $149
Apr 26 - Apr 27
Total with taxes and fees
Hampton Inn White Plains/Tarrytown

Hotel MTK Mount Kisco

Hotel MTK Mount Kisco
3.0 star property
8.2 mi from Pleasant Square
8.6 out of 10, Excellent, (1,000 reviews)
"room is clean, staff are friendly"
United States
Biyuan
$147 nightly
The price is $168
May 3 - May 4
Total with taxes and fees
Hotel MTK Mount Kisco

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
4.0 star property
8.5 mi from Pleasant Square
9.0 out of 10, Wonderful, (1,097 reviews)
"Nice hotel all around."
United States
Dan
$114 nightly
The price is $133
May 10 - May 11
Total with taxes and fees
DoubleTree by Hilton Hotel Nanuet

Armoni Inn & Suites

Armoni Inn & Suites
3.5 star property
9.1 mi from Pleasant Square
6.0 out of 10, (2,181 reviews)
"Very nice staff, the front desk rep was great...the room was fine...nice shower, TV, microwave, albig fridge and the ice-maker was rightbacross the hall and worked well. The mattress and pillows were great and the room was very clean, it just needed some updating and sprucing up...all n all the place was great and you can't beat the price!"
United States
robert
$74 nightly
The price is $82
Apr 26 - Apr 27
Total with taxes and fees
Armoni Inn & Suites

Quality Inn Spring Valley - Nanuet

Quality Inn Spring Valley - Nanuet
2.5 star property
9.4 mi from Pleasant Square
6.2 out of 10, (1,000 reviews)
"Clean room "
United States
DIPEN
$89 nightly
The price is $104
May 3 - May 4
Total with taxes and fees
Quality Inn Spring Valley - Nanuet

Element Spring Valley

Element Spring Valley
3.0 star property
9.2 mi from Pleasant Square
8.8 out of 10, Excellent, (472 reviews)
"Great place to stay."
United States
Jean Fritz Junior
$134 nightly
The price is $156
Apr 26 - Apr 27
Total with taxes and fees
Element Spring Valley

Sonesta Simply Suites Nanuet

Sonesta Simply Suites Nanuet
2.5 star property
9.4 mi from Pleasant Square
8.4 out of 10, Very Good, (1,163 reviews)
"Great Stay Would Definitely Stay Again"
United States
Antwon
$95 nightly
The price is $111
Apr 30 - May 1
Total with taxes and fees
Sonesta Simply Suites Nanuet
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 Pleasant Square attractions

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 41 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 Ly New York Hotel and Hotel Belleclaire.
How many hotels can I expect to find near Pleasant Square?
Expedia has 41 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 Rockwood Hall Park.

Explore a world of travel with Expedia