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10 Jul - 11 Jul
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11 Jul - 13 Jul
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Top Hotels Close to Pleasant Square

Windrose On Hudson
Terrace/patio

Windrose On Hudson

2.0 star property
5.0 out of 10, (2)
"I regret I didn’t take pictures, but the scenery was beautiful"
The price is £204
includes taxes & fees
13 Jul - 14 Jul
Windrose On Hudson
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
Indulge in a variety of hot and cold options at our buffet.

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

2.5 star property
8.8 out of 10, Excellent, (824)
"Spotless, well appointed rooms, excellent location, superior staff."
The price is £167
includes taxes & fees
14 Jul - 15 Jul
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
Courtyard by Marriott Tarrytown Westchester County
Enjoy dining and socializing in this stylish kitchen with a central island and bar.

Courtyard by Marriott Tarrytown Westchester County

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Fantastic hotel. Quiet, out of the way. I always enjoy staying here when visiting Sleepy Hollow/Tarrytown"
The price is £134
includes taxes & fees
3 Aug - 4 Aug
Courtyard by Marriott Tarrytown Westchester County
Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG
Enjoy a wide selection of dishes at our buffet, featuring omelets, cheese, and more.

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

2.5 star property
9.2 out of 10, Wonderful, (1003)
"Would stay again"
The price is £104
includes taxes & fees
15 Jul - 16 Jul
Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG
Westchester Marriott
Experience the modern lobby with a digital reception desk, comfortable seating, and a touch of greenery.

Westchester Marriott

4.5 star property
8.8 out of 10, Excellent, (317)
"Great hotel, well maintained"
The price is £149
includes taxes & fees
3 Aug - 4 Aug
Westchester Marriott
Cambria Hotel White Plains - Downtown
Relax in the stylish lobby, featuring a comfortable seating area with a sofa, coffee table, and vibrant artwork.

Cambria Hotel White Plains - Downtown

3.5 star property
9.4 out of 10, Exceptional, (1003)
"Great staff and hotel"
The price is £171
includes taxes & fees
27 Jul - 28 Jul
Cambria Hotel White Plains - Downtown
Hotel Nyack, a JdV by Hyatt Hotel
Relax in our spacious lobby with sofas, armchairs, and large windows offering a view of the outside.

Hotel Nyack, a JdV by Hyatt Hotel

4.0 star property
8.4 out of 10, Very good, (1003)
"Nice restaurant "
The price is £105
includes taxes & fees
5 Aug - 6 Aug
Hotel Nyack, a JdV by Hyatt Hotel
The Abbey Inn & Spa
Stroll through the beautifully landscaped grounds, surrounded by flowering plants and large rocks, leading to a building with a unique tower.

The Abbey Inn & Spa

4.0 star property
9.2 out of 10, Wonderful, (185)
"Thanks for a great stay!!"
The price is £307
includes taxes & fees
13 Jul - 14 Jul
The Abbey Inn & Spa
The Opus Westchester, Autograph Collection
Welcome to The Opus, where guests enter through a grand entrance flanked by columns and a prominent glass door.

The Opus Westchester, Autograph Collection

5.0 star property
9.2 out of 10, Wonderful, (500)
"Great experience, will highly recommend."
The price is £268
includes taxes & fees
3 Aug - 4 Aug
The Opus Westchester, Autograph Collection
SpringHill Suites by Marriott Tarrytown Westchester County
Welcome to Springhill Suites, featuring a modern entrance with a covered seating area.

SpringHill Suites by Marriott Tarrytown Westchester County

3.0 star property
8.4 out of 10, Very good, (1003)
"Location"
The price is £142
includes taxes & fees
27 Jul - 28 Jul
SpringHill Suites by Marriott Tarrytown Westchester County
Element Spring Valley
Relax in our inviting lobby, featuring a comfortable seating area, dining space, and large windows offering a view of the outdoors.

Element Spring Valley

3.0 star property
8.8 out of 10, Excellent, (375)
"Great place , great breakfast, great staff!! "
The price is £122
includes taxes & fees
3 Aug - 4 Aug
Element Spring Valley
Baymont by Wyndham White Plains - Elmsford
Relax in our spacious lobby with a seating area, food counter, and large window offering a view of the surrounding greenery.

Baymont by Wyndham White Plains - Elmsford

2.5 star property
8.2 out of 10, Very good, (1375)
"Great affordable location ."
The price is £127
includes taxes & fees
27 Jul - 28 Jul
Baymont by Wyndham White Plains - Elmsford
Residence Inn Orangeburg
Relax and socialize in this outdoor patio area, featuring a fire pit and comfortable seating.

Residence Inn Orangeburg

3.0 star property
8.8 out of 10, Excellent, (1006)
"Love the area and the history "
The price is £125
includes taxes & fees
10 Aug - 11 Aug
Residence Inn Orangeburg
Sheraton Tarrytown Hotel
Experience the welcoming atmosphere of this Sheraton hotel, where guests can enjoy a convenient entrance via a covered walkway and beautifully landscaped surroundings.

Sheraton Tarrytown Hotel

3.5 star property
8.2 out of 10, Very good, (1002)
"Convenient location, easy check in, good for access to multiple sights of interest. "
The price is £114
includes taxes & fees
3 Aug - 4 Aug
Sheraton Tarrytown Hotel
Hotel MTK Mount Kisco
Relax in the inviting lobby with a comfortable sofa, armchair, and leather chair, surrounded by a stone accent wall and a cozy fireplace.

Hotel MTK Mount Kisco

3.0 star property
8.4 out of 10, Very good, (1002)
"Very friendly staff!"
The price is £142
includes taxes & fees
3 Aug - 4 Aug
Hotel MTK Mount Kisco
Residence Inn by Marriott White Plains Westchester County
Experience the Residence Inn's contemporary design, featuring spacious balconies and large windows, amidst a serene courtyard with lush greenery.

Residence Inn by Marriott White Plains Westchester County

3.0 star property
8.6 out of 10, Excellent, (615)
"Excellent service and rooms"
The price is £150
includes taxes & fees
3 Aug - 4 Aug
Residence Inn by Marriott White Plains Westchester County
Sonesta Simply Suites Nanuet
Relax in a serene outdoor space with a round table and comfortable seating.

Sonesta Simply Suites Nanuet

2.5 star property
8.4 out of 10, Very good, (1010)
"Great location and room. Would stay again. "
The price is £102
includes taxes & fees
28 Jul - 29 Jul
Sonesta Simply Suites Nanuet
Tarrytown House Estate
Relax by the serene pool surrounded by lounge chairs and umbrellas, with a castle-like building in the background.

Tarrytown House Estate

3.5 star property
8.0 out of 10, Very good, (1012)
"Beautiful property in a beautiful town."
The price is £180
includes taxes & fees
27 Jul - 28 Jul
Tarrytown House Estate
Sonesta White Plains Downtown
Relax by the rectangular pool surrounded by lounge chairs and a bench.

Sonesta White Plains Downtown

4.0 star property
8.6 out of 10, Excellent, (1089)
"Great place"
The price is £167
includes taxes & fees
3 Aug - 4 Aug
Sonesta White Plains Downtown
FairBridge Inn Express Nyack
Relax in our spacious lobby, featuring a seating area with sofas and armchairs, a small table, and a graphic wall sign.

FairBridge Inn Express Nyack

2.0 star property
7.6 out of 10, Good, (1003)
"This property is completely remodeled, a 90% improvement under the new management. I would stay here again and recommend it"
The price is £83
includes taxes & fees
17 Jul - 18 Jul
FairBridge Inn Express Nyack
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.

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 34 hotels and other accommodations within a few miles for a convenient home base.

Where is the best place to stay close to Pleasant Square?

Radio Hotel is one of the top choices for your stay based on our traveller data, and this hotel offers a restaurant and a 24-hour fitness centre. You'll find it 22 mi (35.4 km) from Pleasant Square. Other good options around the area include Hotel MOCA NYC and Night Hotel Broadway.

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

Expedia has 34 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.