Search Hotels Near Pleasant Square, Ossining

    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
Property class

Top Trending Hotels Near Pleasant Square

Our top choices for Pleasant Square hotels

Windrose On Hudson

3.0 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 5.787.951 ₫
6.446.297 ₫ total
includes taxes & fees
24 Aug - 25 Aug
Windrose On Hudson

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

2.5 star property
8.8 out of 10, Excellent, (850)
"the beds were very comfortable, "
The price is 4.457.037 ₫
5.097.734 ₫ total
includes taxes & fees
1 Sept - 2 Sept
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, (1001)
"Nice hotel"
The price is 4.246.053 ₫
4.856.424 ₫ total
includes taxes & fees
31 Aug - 1 Sept
Courtyard by Marriott Tarrytown Westchester County

Days Inn by Wyndham Nanuet / Spring Valley

2.0 star property
6.8 out of 10, (1003)
"It was a wonderful stay at the hotel"
The price is 2.219.288 ₫
2.582.695 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Days Inn by Wyndham Nanuet / Spring Valley

Extended Stay America Suites White Plains Elmsford

2.5 star property
6.8 out of 10, (1001)
"Good location . Clean and staff very friendly "
The price is 3.204.056 ₫
3.664.529 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Extended Stay America Suites White Plains Elmsford

Westchester Marriott

4.5 star property
8.8 out of 10, Excellent, (342)
"Great stay - would def stay there again!"
The price is 4.414.840 ₫
5.049.473 ₫ total
includes taxes & fees
31 Aug - 1 Sept
Westchester Marriott

Hotel Nyack, a JdV by Hyatt Hotel

4.0 star property
8.6 out of 10, Excellent, (1003)
"Very clean .. staff super nice "
The price is 2.642.900 ₫
3.738.778 ₫ total
includes taxes & fees
2 Sept - 3 Sept
Hotel Nyack, a JdV by Hyatt Hotel

Days Inn by Wyndham Elmsford / White Plains

2.0 star property
6.6 out of 10, (1001)
"Staff is nice and professional. Breakfast is good as well."
The price is 2.396.251 ₫
2.740.714 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Days Inn by Wyndham Elmsford / White Plains

Sleepy Hollow Hotel

3.5 star property
6.8 out of 10, (1002)
"Amazing place "
The price is 4.630.361 ₫
5.295.976 ₫ total
includes taxes & fees
21 Sept - 22 Sept
Sleepy Hollow Hotel

Baymont by Wyndham White Plains - Elmsford

2.5 star property
8.2 out of 10, Very good, (1397)
"Super comfy bed breakfast was great "
The price is 3.586.728 ₫
4.102.322 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Baymont by Wyndham White Plains - Elmsford

FairBridge Inn Express Nyack

2.0 star property
7.6 out of 10, Good, (1000)
"Great World Market across the street. Clean and efficient place to stay. Continental breakfast "
The price is 2.353.790 ₫
2.809.835 ₫ total
includes taxes & fees
4 Sept - 5 Sept
FairBridge Inn Express Nyack

Tappan Zee Hotel

2.0 star property
6.4 out of 10, (607)
"Good location, next to mall."
Tappan Zee Hotel

Inn on the Hudson

2.0 star property
6.8 out of 10, (1004)
"Lovely location and view. Very nice folks and clean and helpful. "
The price is 3.006.522 ₫
3.438.775 ₫ total
includes taxes & fees
31 Aug - 1 Sept
Inn on the Hudson

West Gate Inn Nyack

3.0 star property
7.4 out of 10, Good, (1019)
"Great place to stay I”ll recommend it "
The price is 3.428.226 ₫
3.921.137 ₫ total
includes taxes & fees
29 Aug - 30 Aug
West Gate Inn Nyack

Armoni Inn & Suites

3.5 star property
6.0 out of 10, (1988)
"The area is very quiet and the pool is great also very great staff"
The price is 1.901.229 ₫
2.117.493 ₫ total
includes taxes & fees
2 Sept - 3 Sept
Armoni Inn & Suites

SpringHill Suites by Marriott Tarrytown Westchester County

3.0 star property
8.4 out of 10, Very good, (1000)
"Decent hotel."
The price is 3.788.481 ₫
4.333.074 ₫ total
includes taxes & fees
31 Aug - 1 Sept
SpringHill Suites by Marriott Tarrytown Westchester County

Motel 6 Elmsford, NY - White Plains

2.0 star property
6.4 out of 10, (830)
"We liked that it was quiet and clean."
The price is 2.874.657 ₫
3.287.922 ₫ total
includes taxes & fees
31 Aug - 1 Sept
Motel 6 Elmsford, NY - White Plains

Quality Inn Spring Valley - Nanuet

2.5 star property
6.2 out of 10, (1004)
"bed was comfy, clean rooms"
The price is 2.254.628 ₫
2.623.822 ₫ total
includes taxes & fees
3 Sept - 4 Sept
Quality Inn Spring Valley - Nanuet

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

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Would stay again"
The price is 3.665.847 ₫
4.192.813 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG

Hampton Inn White Plains/Tarrytown

3.0 star property
7.8 out of 10, Good, (1128)
"Easy check in and breakfast was amazing"
The price is 3.340.140 ₫
3.820.284 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Hampton Inn White Plains/Tarrytown
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

Destinations near Ossining

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.

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

Expedia has 35 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 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.