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

Star rating

Guest rating

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

Our top choices for Pleasant Square hotels

1. Windrose On Hudson

Windrose On Hudson
3.0 star property
3.1 km from Pleasant Square
8.6 out of 10, Excellent, (204 reviews)
The price is Rp3.414.723
Rp3.803.147 total
includes taxes & fees
19 Aug - 20 Aug
Windrose On Hudson

2. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
0.7 km from Pleasant Square
The price is Rp18.545.834
Rp29.344.342 total
includes taxes & fees
4 Aug - 5 Aug
Summer Pool Oasis Custom Bar Arcade Pool Table

3. 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, (1,186 reviews)
"Convenient, safe and very clean and quiet."
United States
Joyce
The price is Rp2.209.381
Rp2.571.169 total
includes taxes & fees
12 Aug - 13 Aug
DoubleTree by Hilton Hotel Nanuet

4. 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, (1,013 reviews)
"Room was spacious and clean. My children enjoyed the pool and gym. Will definitely stay again."
United States
Silvia
The price is Rp2.252.206
Rp2.575.961 total
includes taxes & fees
2 Aug - 3 Aug
Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

5. 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, (1,780 reviews)
"Clean rooms and indoor pool is a plus"
United States
Michael
The price is Rp2.428.728
Rp2.777.857 total
includes taxes & fees
12 Aug - 13 Aug
Baymont by Wyndham White Plains - Elmsford

6. Hotel MTK Mount Kisco

Hotel MTK Mount Kisco
3.0 star property
13.2 km from Pleasant Square
8.6 out of 10, Excellent, (1,007 reviews)
"The staff was super friendly!"
United States
Ellen
The price is Rp2.643.361
Rp3.023.345 total
includes taxes & fees
23 Aug - 24 Aug
Hotel MTK Mount Kisco

7. 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, (1,573 reviews)
"It was a great stay!"
United States
Dominique
The price is Rp2.046.272
Rp2.340.424 total
includes taxes & fees
9 Aug - 10 Aug
Hampton Inn White Plains/Tarrytown

8. Cambria Hotel & Suites - White Plains Downtown

Cambria Hotel & Suites - White Plains Downtown
3.5 star property
16.5 km from Pleasant Square
9.4 out of 10, Exceptional, (1,015 reviews)
"Great stay"
United States
Matthew
The price is Rp3.299.249
Rp3.773.518 total
includes taxes & fees
23 Aug - 24 Aug
Cambria Hotel & Suites - White Plains Downtown

9. Ardsley Acres Hotel Westchester

Ardsley Acres Hotel Westchester
2.0 star property
17.1 km from Pleasant Square
8.8 out of 10, Excellent, (1,109 reviews)
"Always a great stay"
United States
Sylvia
The price is Rp2.208.264
Rp2.525.942 total
includes taxes & fees
30 Jul - 31 Jul
Ardsley Acres Hotel Westchester

10. 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, (1,197 reviews)
"Great hotel if you are in that area."
United States
Jacob Glauco
The price is Rp2.296.541
Rp3.116.537 total
includes taxes & fees
20 Aug - 21 Aug
Hotel Nyack, a JdV by Hyatt Hotel

11. 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, (1,001 reviews)
"Really excellent hotel all around. Just as nice as a place far more expensive."
United States
Clara
The price is Rp2.751.328
Rp3.146.831 total
includes taxes & fees
2 Aug - 3 Aug
Courtyard by Marriott Tarrytown Westchester County

12. 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, (1,010 reviews)
"Enjoyed our stay"
United States
Piper
The price is Rp2.750.424
Rp3.145.798 total
includes taxes & fees
2 Aug - 3 Aug
SpringHill Suites by Marriott Tarrytown Westchester County

13. Westchester Marriott

Westchester Marriott
4.5 star property
11.7 km from Pleasant Square
8.8 out of 10, Excellent, (604 reviews)
"Great place. "
United States
Richard
The price is Rp3.385.692
Rp3.872.384 total
includes taxes & fees
20 Aug - 21 Aug
Westchester Marriott

14. 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, (1,009 reviews)
"Great stay"
United States
Lorraine
The price is Rp2.869.049
Rp3.281.522 total
includes taxes & fees
20 Aug - 21 Aug
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

15. Tarrytown House Estate

Tarrytown House Estate
3.5 star property
12.5 km from Pleasant Square
8.2 out of 10, Very good, (1,206 reviews)
"Gorgeous estate. Can’t wait to go back!"
United States
Chelsea
The price is Rp2.704.674
Rp3.545.534 total
includes taxes & fees
2 Aug - 3 Aug
Tarrytown House Estate

16. HYATT house White Plains

HYATT house White Plains
3.0 star property
19.6 km from Pleasant Square
8.8 out of 10, Excellent, (1,134 reviews)
"Excellent location, comfortable rooms, and very good breakfast."
United States
Patrick
The price is Rp3.238.665
Rp3.704.223 total
includes taxes & fees
6 Aug - 7 Aug
HYATT house White Plains

17. The Abbey Inn & Spa

The Abbey Inn & Spa
4.0 star property
15.6 km from Pleasant Square
9.2 out of 10, Wonderful, (262 reviews)
"The service was exceptional, room was amazing and very clean. Property is stunning and the spa was lovely. The restaurant in the hotel was delicious too. I highly recommend for a getaway!"
United States
Izabella
The price is Rp5.632.538
Rp7.269.512 total
includes taxes & fees
2 Aug - 3 Aug
The Abbey Inn & Spa

18. Sonesta White Plains Downtown

Sonesta White Plains Downtown
4.0 star property
17 km from Pleasant Square
8.8 out of 10, Excellent, (1,340 reviews)
"Beautiful hotel. And pleasant staff. I would definitely recommend and return for another stay"
United States
Angela Marquita
The price is Rp3.218.774
Rp4.281.285 total
includes taxes & fees
2 Aug - 3 Aug
Sonesta White Plains Downtown

19. 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, (504 reviews)
"Our room was clean and spacious. The staff was very kind and helped with anything we needed. Would stay here again!"
United States
Michael
The price is Rp2.513.537
Rp2.925.130 total
includes taxes & fees
16 Aug - 17 Aug
Element by Marriott Spring Valley

20. Residence Inn Orangeburg

Residence Inn Orangeburg
3.0 star property
15.4 km from Pleasant Square
8.8 out of 10, Excellent, (1,004 reviews)
"Clean up room and excellent staff."
United States
Maria
The price is Rp2.739.169
Rp3.050.749 total
includes taxes & fees
13 Aug - 14 Aug
Residence Inn Orangeburg
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

Other attractions near Pleasant Square

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 43 hotels and other accommodations within a few miles for a convenient home base.
Where is the best place to stay close to Pleasant Square?
Highbridge Hotel is one of the top choices for your stay based on our traveller data, and this hotel offers free breakfast and a fitness centre. You'll find it 22.7 mi (36.5 km) from Pleasant Square. Other good options around the area include Night Hotel Broadway and Arthouse Hotel New York City.
How many hotels should I expect to find near Pleasant Square?
Expedia has 43 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, Rockland Lake State Park or Louis Engel Waterfront Park.