The Best Hotels Closest to Pleasant Square in Ossining - 2026 Updated Prices

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Our top choices for Pleasant Square hotels

Room, 1 Queen Bed, Mobility Accessible | Desk, laptop workspace, iron/ironing board, free cots/infant beds

1. Windrose On Hudson

3.1 km from Pleasant Square

Rp3.803.147 total

includes taxes & fees

19 Aug - 20 Aug

2. Summer Pool Oasis Custom Bar Arcade Pool Table

0.7 km from Pleasant Square

Rp29.344.342 total

includes taxes & fees

4 Aug - 5 Aug

Indoor pool, open 8:30 AM to 9:30 PM, pool loungers

3. DoubleTree by Hilton Hotel Nanuet

13.8 km from Pleasant Square

Joyce

Rp2.571.169 total

includes taxes & fees

12 Aug - 13 Aug

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

14.4 km from Pleasant Square

Silvia

Rp2.575.961 total

includes taxes & fees

2 Aug - 3 Aug

5. Baymont by Wyndham White Plains - Elmsford

10.9 km from Pleasant Square

Michael

Rp2.777.857 total

includes taxes & fees

12 Aug - 13 Aug

6. Hotel MTK Mount Kisco

13.2 km from Pleasant Square

Ellen

Rp3.023.345 total

includes taxes & fees

23 Aug - 24 Aug

7. Hampton Inn White Plains/Tarrytown

12 km from Pleasant Square

Dominique

Rp2.340.424 total

includes taxes & fees

9 Aug - 10 Aug

8. Cambria Hotel & Suites - White Plains Downtown

16.5 km from Pleasant Square

Matthew

Rp3.773.518 total

includes taxes & fees

23 Aug - 24 Aug

Standard Room, 1 King Bed | Premium bedding, desk, iron/ironing board, free WiFi

9. Ardsley Acres Hotel Westchester

17.1 km from Pleasant Square

Sylvia

Rp2.525.942 total

includes taxes & fees

30 Jul - 31 Jul

10. Hotel Nyack, a JdV by Hyatt Hotel

9.5 km from Pleasant Square

Jacob Glauco

Rp3.116.537 total

includes taxes & fees

20 Aug - 21 Aug

11. Courtyard by Marriott Tarrytown Westchester County

10.9 km from Pleasant Square

Clara

Rp3.146.831 total

includes taxes & fees

2 Aug - 3 Aug

12. SpringHill Suites by Marriott Tarrytown Westchester County

11.2 km from Pleasant Square

Piper

Rp3.145.798 total

includes taxes & fees

2 Aug - 3 Aug

13. Westchester Marriott

11.7 km from Pleasant Square

Richard

Rp3.872.384 total

includes taxes & fees

20 Aug - 21 Aug

14. Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

8.5 km from Pleasant Square

Lorraine

Rp3.281.522 total

includes taxes & fees

20 Aug - 21 Aug

15. Tarrytown House Estate

12.5 km from Pleasant Square

Chelsea

Rp3.545.534 total

includes taxes & fees

2 Aug - 3 Aug

16. HYATT house White Plains

19.6 km from Pleasant Square

Patrick

Rp3.704.223 total

includes taxes & fees

6 Aug - 7 Aug

17. The Abbey Inn & Spa

15.6 km from Pleasant Square

Izabella

Rp7.269.512 total

includes taxes & fees

2 Aug - 3 Aug

18. Sonesta White Plains Downtown

17 km from Pleasant Square

Angela Marquita

Rp4.281.285 total

includes taxes & fees

2 Aug - 3 Aug

19. Element by Marriott Spring Valley

14.8 km from Pleasant Square

Michael

Rp2.925.130 total

includes taxes & fees

16 Aug - 17 Aug

20. Residence Inn Orangeburg

15.4 km from Pleasant Square

Maria

Rp3.050.749 total

includes taxes & fees

13 Aug - 14 Aug

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Top Pleasant Square Hotel Reviews

Highbridge Hotel

10/10 Excellent

"The room was very clean, comfortable, spacious and great."

Nap York Central Park Sleep Station

8/10 Good

"The rooms are very clean and well maintained. I liked that there were lockers available to use and that they were full size. It was larger enough to fit a carry on luggage and a back pack, and had shelves and hooks that were useful to hang up clothing or store shoes. The bunk beds were pretty comfortable too and had a shelf, charging ports, hooks, a reading light, and even a small fan. The rooms were very well ventilated and even with 5 other roommates it stayed cool. I liked that there were both private and communal bathrooms/showers and they were cleaned daily by staff. There was a pretty chill living area as well to eat in or get work done. I thought that it was really cool that there was even a vending machine that sold basic necessities in case you forgot anything, and even had snacks, ramen, and drinks for a reasonable price. The only thing that I wish was that there was a stove/oven. But the kitchen was otherwise very useful and equipped with a sink, fridge, and cabinets to store stuff in so long as you labeled your items. There was also a shelving unit/area to store your luggage in in case you check in early. It is unguarded and in an open space so I would suggest a luggage lock if you plan to use the space to store your luggage."

Other attractions near Pleasant Square

Merchants Square

9.0/10 (2 reviews)

Explore the great outdoors at Merchants Square, a lovely green space in Ossining. Stroll along the riverfront or attend a sporting event in this family-friendly area.

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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.

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Our top choices for Pleasant Square hotels

1. Windrose On Hudson

2. Summer Pool Oasis Custom Bar Arcade Pool Table

3. DoubleTree by Hilton Hotel Nanuet

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

5. Baymont by Wyndham White Plains - Elmsford

6. Hotel MTK Mount Kisco

7. Hampton Inn White Plains/Tarrytown

8. Cambria Hotel & Suites - White Plains Downtown

9. Ardsley Acres Hotel Westchester

10. Hotel Nyack, a JdV by Hyatt Hotel

11. Courtyard by Marriott Tarrytown Westchester County

12. SpringHill Suites by Marriott Tarrytown Westchester County

13. Westchester Marriott

14. Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

15. Tarrytown House Estate

16. HYATT house White Plains

17. The Abbey Inn & Spa

18. Sonesta White Plains Downtown

19. Element by Marriott Spring Valley

20. Residence Inn Orangeburg

Top Pleasant Square Hotel Reviews

Highbridge Hotel

Other attractions near Pleasant Square

Merchants Square

Frequently asked questions