Search Hotels Near Pleasant Square, Ossining

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Top Trending Hotels Near Pleasant Square

Windrose On Hudson

2.0 star property
8.0 out of 10, Very good, (1)
"I regret I didn’t take pictures, but the scenery was beautiful"
The price is ₹19,628
₹21,861 total
includes taxes & fees
3 Jul - 4 Jul
Windrose On Hudson

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

2.5 star property
8.8 out of 10, Excellent, (811)
"Spotless, well appointed rooms, excellent location, superior staff."
The price is ₹15,343
₹17,548 total
includes taxes & fees
29 Jun - 30 Jun
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)
"Fantastic hotel. Quiet, out of the way. I always enjoy staying here when visiting Sleepy Hollow/Tarrytown"
The price is ₹15,217
₹17,404 total
includes taxes & fees
10 Jul - 11 Jul
Courtyard by Marriott Tarrytown Westchester County

Westchester Marriott

4.5 star property
8.8 out of 10, Excellent, (309)
"The stay was great!"
The price is ₹14,348
₹16,411 total
includes taxes & fees
2 Jul - 3 Jul
Westchester Marriott

Cambria Hotel White Plains - Downtown

3.5 star property
9.4 out of 10, Exceptional, (1002)
"Staff at front desk were awesome. Hotel was clean and comfortable. Located in a great area. I would definitely stay here again, and recommend it to friends "
The price is ₹17,412
₹19,916 total
includes taxes & fees
13 Jul - 14 Jul
Cambria Hotel White Plains - Downtown

Hotel Nyack, a JdV by Hyatt Hotel

4.0 star property
8.4 out of 10, Very good, (1010)
"lovely boutique hotel."
The price is ₹8,486
₹12,027 total
includes taxes & fees
20 Jul - 21 Jul
Hotel Nyack, a JdV by Hyatt Hotel

The Opus Westchester, Autograph Collection

5.0 star property
9.2 out of 10, Wonderful, (499)
"Great experience, will highly recommend."
The price is ₹27,342
₹31,273 total
includes taxes & fees
30 Jun - 1 Jul
The Opus Westchester, Autograph Collection

DoubleTree by Hilton Hotel Nanuet

4.0 star property
8.8 out of 10, Excellent, (1001)
"nice hotel"
The price is ₹10,828
₹12,601 total
includes taxes & fees
27 Jul - 28 Jul
DoubleTree by Hilton Hotel Nanuet

SpringHill Suites by Marriott Tarrytown Westchester County

3.0 star property
8.4 out of 10, Very good, (1010)
"Location"
The price is ₹12,280
₹14,046 total
includes taxes & fees
10 Jul - 11 Jul
SpringHill Suites by Marriott Tarrytown Westchester County

Element Spring Valley

3.0 star property
8.8 out of 10, Excellent, (371)
"Great place , great breakfast, great staff!! "
The price is ₹12,257
₹14,264 total
includes taxes & fees
13 Jul - 14 Jul
Element Spring Valley

Baymont by Wyndham White Plains - Elmsford

2.5 star property
8.2 out of 10, Very good, (1363)
"Great stay"
The price is ₹12,458
₹14,249 total
includes taxes & fees
29 Jun - 30 Jun
Baymont by Wyndham White Plains - Elmsford

Sheraton Tarrytown Hotel

3.5 star property
8.2 out of 10, Very good, (1005)
"Convenient location, easy check in, good for access to multiple sights of interest. "
The price is ₹11,584
₹13,249 total
includes taxes & fees
20 Jul - 21 Jul
Sheraton Tarrytown Hotel

Hotel MTK Mount Kisco

3.0 star property
8.4 out of 10, Very good, (1003)
"Clean, quiet, good sheets and pillows."
The price is ₹14,460
₹16,539 total
includes taxes & fees
6 Jul - 7 Jul
Hotel MTK Mount Kisco

Residence Inn by Marriott White Plains Westchester County

3.0 star property
8.6 out of 10, Excellent, (614)
"Excellent service and rooms"
The price is ₹15,217
₹17,404 total
includes taxes & fees
27 Jul - 28 Jul
Residence Inn by Marriott White Plains Westchester County

Sonesta Simply Suites Nanuet

2.5 star property
8.4 out of 10, Very good, (1000)
"Great location and room. Would stay again. "
The price is ₹9,720
₹11,311 total
includes taxes & fees
2 Jul - 3 Jul
Sonesta Simply Suites Nanuet

Tarrytown House Estate

3.5 star property
8.0 out of 10, Very good, (1002)
"Stayed 1 night. What a beautiful hotel. Staff was very friendly, the grounds outside are stunning, well kept and very big. The rooms fit the ambiance. Lots of restaurants close by(car required) with cute shops. We definitely enjoyed our stay and would recommend."
The price is ₹9,469
₹12,540 total
includes taxes & fees
6 Jul - 7 Jul
Tarrytown House Estate

Sonesta White Plains Downtown

4.0 star property
8.6 out of 10, Excellent, (1102)
"Great place"
The price is ₹16,114
₹20,881 total
includes taxes & fees
30 Jun - 1 Jul
Sonesta White Plains Downtown

FairBridge Inn Express Nyack

2.0 star property
7.6 out of 10, Good, (1003)
"Stayed for one night, it was excellent and quiet. Breakfast was pretty good too. I'd stay again"
The price is ₹8,087
₹9,654 total
includes taxes & fees
7 Jul - 8 Jul
FairBridge Inn Express Nyack

Hampton Inn White Plains/Tarrytown

3.0 star property
7.8 out of 10, Good, (1041)
"Good location "
The price is ₹11,554
₹13,214 total
includes taxes & fees
6 Jul - 7 Jul
Hampton Inn White Plains/Tarrytown

West Gate Inn Nyack

3.0 star property
7.4 out of 10, Good, (1006)
"The breakfast is good and the rooms are clean."
The price is ₹10,336
₹11,821 total
includes taxes & fees
11 Jul - 12 Jul
West Gate Inn 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 33 hotels and other accommodations within a few miles for a convenient home base.

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

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

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

Expedia has 33 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.