Default HTG hotel image

Search Hotels Near Pleasant Square, Ossining

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating

Selecting then applying a filter from this group will update the results on a new page

Star rating

Our top choices for Pleasant Square hotels

Windrose On Hudson

Windrose On Hudson
3.0 star property
3.1 km from Pleasant Square
8.6 out of 10, Excellent, (172 reviews)
"Ev chargers on site. Lovely grounds and facilities. Will definitely stay here next time i am in the area."
United States
Andrew
The price is Rp3.669.404
Rp4.086.798 total
includes taxes & fees
24 Jun - 25 Jun
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
8.5 km from Pleasant Square
9.0 out of 10, Wonderful, (1,001 reviews)
"Great location and very nice property"
United States
William
The price is Rp2.492.560
Rp2.850.955 total
includes taxes & fees
5 Jul - 6 Jul
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
9.5 km from Pleasant Square
8.6 out of 10, Excellent, (1,154 reviews)
"All staff were courteous and helpful. Chic rooms and everything was super clean! We had a great stay!"
United States
Jillian
The price is Rp1.925.452
Rp2.684.546 total
includes taxes & fees
8 Jul - 9 Jul
Hotel Nyack, a JdV by Hyatt Hotel

Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford
2.5 star property
10.9 km from Pleasant Square
8.4 out of 10, Very good, (1,723 reviews)
"Had a great stay at this property, resonably priced with good ammenities and clean rooms."
United States
Jaime
The price is Rp2.547.752
Rp2.913.994 total
includes taxes & fees
28 Jun - 29 Jun
Baymont by Wyndham White Plains - Elmsford

Courtyard by Marriott Tarrytown Westchester County

Courtyard by Marriott Tarrytown Westchester County
3.0 star property
10.9 km from Pleasant Square
9.0 out of 10, Wonderful, (1,003 reviews)
"Really excellent hotel all around. Just as nice as a place far more expensive."
United States
Clara
The price is Rp3.329.348
Rp3.807.942 total
includes taxes & fees
28 Jun - 29 Jun
Courtyard by Marriott Tarrytown Westchester County

Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown
3.0 star property
12 km from Pleasant Square
8.0 out of 10, Very good, (1,514 reviews)
"It was a great stay!"
United States
Dominique
The price is Rp2.128.646
Rp2.434.697 total
includes taxes & fees
2 Jul - 3 Jul
Hampton Inn White Plains/Tarrytown

West Gate Inn Nyack

West Gate Inn Nyack
3.0 star property
9.6 km from Pleasant Square
7.2 out of 10, Good, (1,345 reviews)
"Great location. Amazing breakfast."
United States
Gareth
The price is Rp1.762.418
Rp2.015.769 total
includes taxes & fees
23 Jun - 24 Jun
West Gate Inn Nyack

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
4.0 star property
13.8 km from Pleasant Square
9.0 out of 10, Wonderful, (1,153 reviews)
"Well maintained property. Comfortable bed. Staff was very friendly. Location is great"
United States
Norman
The price is Rp2.175.293
Rp2.531.499 total
includes taxes & fees
6 Jul - 7 Jul
DoubleTree by Hilton Hotel Nanuet

FairBridge Inn Express Nyack

FairBridge Inn Express Nyack
2.0 star property
9.8 km from Pleasant Square
7.8 out of 10, Good, (1,005 reviews)
"The best hotel!!!"
United States
Paige
The price is Rp1.842.714
Rp2.199.741 total
includes taxes & fees
6 Jul - 7 Jul
FairBridge Inn Express Nyack

SpringHill Suites by Marriott Tarrytown Westchester County

SpringHill Suites by Marriott Tarrytown Westchester County
3.0 star property
11.2 km from Pleasant Square
8.6 out of 10, Excellent, (1,003 reviews)
"Enjoyed our stay"
United States
Piper
The price is Rp2.772.617
Rp3.171.179 total
includes taxes & fees
5 Jul - 6 Jul
SpringHill Suites by Marriott Tarrytown Westchester County

Sheraton Tarrytown Hotel

Sheraton Tarrytown Hotel
3.5 star property
11.4 km from Pleasant Square
8.4 out of 10, Very good, (1,004 reviews)
"Every things was fine here-this is our go to hotel when we are in the area. I only wish the bar/restaurant was open later."
United States
Ciaran
The price is Rp2.860.213
Rp3.271.369 total
includes taxes & fees
28 Jun - 29 Jun
Sheraton Tarrytown Hotel

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

Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG
2.5 star property
14.4 km from Pleasant Square
9.2 out of 10, Wonderful, (1,003 reviews)
"Great place to stay. "
United States
Jennifer
The price is Rp2.706.208
Rp3.095.225 total
includes taxes & fees
5 Jul - 6 Jul
Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

Westchester Marriott

Westchester Marriott
4.5 star property
11.7 km from Pleasant Square
8.8 out of 10, Excellent, (563 reviews)
"Great stay"
United States
Leneir
The price is Rp3.667.624
Rp4.194.844 total
includes taxes & fees
28 Jun - 29 Jun
Westchester Marriott

Tappan Zee Hotel

Tappan Zee Hotel
2.0 star property
10.4 km from Pleasant Square
6.4 out of 10, (677 reviews)
"Great stay…."
United States
Mariya
The price is Rp1.721.113
Rp2.002.950 total
includes taxes & fees
27 Jun - 28 Jun
Tappan Zee Hotel

Hotel MTK Mount Kisco

Hotel MTK Mount Kisco
3.0 star property
13.2 km from Pleasant Square
8.6 out of 10, Excellent, (1,001 reviews)
"Staff was very helpful and room was very clean!!"
United States
Andrea
The price is Rp2.759.264
Rp3.155.909 total
includes taxes & fees
28 Jun - 29 Jun
Hotel MTK Mount Kisco

Armoni Inn & Suites

Armoni Inn & Suites
3.5 star property
14.6 km from Pleasant Square
6.0 out of 10, (2,265 reviews)
"Good value, clean room, plenty of parking"
United States
Mohamed
The price is Rp1.251.799
Rp1.394.191 total
includes taxes & fees
23 Jun - 24 Jun
Armoni Inn & Suites

Motel 6 Elmsford, NY - White Plains

Motel 6 Elmsford, NY - White Plains
2.0 star property
12.2 km from Pleasant Square
6.6 out of 10, (985 reviews)
"Parking good. HVAC good. Bath good. Room floor a little disheveled. Needed more lamps. Very convenient."
United States
Bruce
The price is Rp2.403.540
Rp2.749.116 total
includes taxes & fees
29 Jun - 30 Jun
Motel 6 Elmsford, NY - White Plains

Quality Inn Spring Valley - Nanuet

Quality Inn Spring Valley - Nanuet
2.5 star property
15.2 km from Pleasant Square
6.2 out of 10, (1,002 reviews)
"The staffs are very friendly and rooms are clean."
United States
Anna Lorraine
The price is Rp1.922.654
Rp2.237.488 total
includes taxes & fees
28 Jun - 29 Jun
Quality Inn Spring Valley - Nanuet

Element by Marriott Spring Valley

Element by Marriott Spring Valley
3.0 star property
14.8 km from Pleasant Square
8.8 out of 10, Excellent, (494 reviews)
"Newer hotel with great amenities including daily breakfast. "
United States
Mark
The price is Rp2.633.212
Rp3.064.400 total
includes taxes & fees
12 Jul - 13 Jul
Element by Marriott Spring Valley

Sleepy Hollow Hotel, a Dolce by Wyndham

Sleepy Hollow Hotel, a Dolce by Wyndham
3.5 star property
11.3 km from Pleasant Square
7.0 out of 10, Good, (1,001 reviews)
"Great place to stay. Staff is super friendly, property is beautiful."
United States
Morgan
The price is Rp2.676.101
Rp3.060.789 total
includes taxes & fees
23 Jun - 24 Jun
Sleepy Hollow Hotel, a Dolce by Wyndham
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.

Compare popular hotels close to Pleasant Square

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
Restaurant
Windrose On Hudson
3.0 star property
8.6
Excellent
172 reviews
View
Exterior
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
2.5 star property
9.0
Wonderful
1,001 reviews
View
Restaurant
Hotel Nyack, a JdV by Hyatt Hotel
4.0 star property
8.6
Excellent
1,154 reviews
View
Free daily self-service breakfast
Baymont by Wyndham White Plains - Elmsford
2.5 star property
8.4
Very good
1,723 reviews
View
Property amenity
Courtyard by Marriott Tarrytown Westchester County
3.0 star property
9.0
Wonderful
1,003 reviews
View

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 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 traveller 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 should I expect to find near Pleasant Square?
Expedia has 46 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 Merchants Square.